Shuffle Around Life: Chapter 4 (2, Q, 4), Dating App Tips Series: Hinge and the Holiday Season

What’s up everyone and welcome to Part 2 of our DAT TRP Series. We already covered OkCupid so if you’re curious about the issue you can click here or work your way from the Beginning of the Shuffle Around Life series.

Hinge is an app that was popularized in New York, gained traction in LA and slowly crept and crawled throughout the country. One of the key differences with this app compared to OkCupid is it’s minimalist settings. Originally you had to sync your Facebook account in order to “acquire the friends of friends network aka your prospective dating pool” to see what you’re working with. As of the writing of this article, you can now sign up with just an email. You can do either way, however for me I started with Sync’ing my own FB account and went from there.

When you first start you need to set your Preferences, who are you interested in (are you interested in the same sex, opposite sex, or you like to grab from both genders). Unfortunately for certain LGBT individuals this may be off putting. Afterwards you need to turn on Location Settings because you need to “Claim your hood.” Then you have to set all the other demographic data: Age Range, Maximum Distance and more. One of the key features that stand out as a filter is the “Is this a Dealbreaker?”

If you’re one of those people that likes to sample the entire world’s buffet, then never turn on that option. However if Religion, Maximum Distance (which only covers 100 miles, talk about limited parameters) and more are truly important for you, then by all means switch on and indicate “It is a Dealbreaker?” It will be marked with ‘Dealbreaker’ in the preference setting, so you can set it and forget it. Now me personally, unlike OkCupid you cannot filter by fitness preferences (seems superficial and probably better for overall user experience) but for those of us who want someone a bit more active, than average (and that’s not asking much) this is one of my few qualms about it. One other thing to note is, while OkCupid still has a slant (no pun intended) to favor Caucasian Males and Asian Females. This app caters to a similar audience (it’s not to throw shade it’s the facts), so if you love Basic Becky/Techies (70%) then you’re probably in Nirvana. There are a portion of Minority Females but the breakdown before I placed my filters were (20% Asian and 5-10% Latino/Hispanic or African American given your geographic location). You don’t have to fill out everything but you should definitely address everything, if you want to take this thing seriously. Your mileage may vary and as an Asian-American male my experience is much more unique than let’s say someone who is Caucasian or African-American. When thinking about how you want to convey yourself to your dating prospects be mindful to:

It’s very important to setup your profile sections, you need to optimize: six pictures, three answer prompts, seven virtues, eight vitals, four vices, and the option of syncing your Instagram (sounds like the 12 days of Christmas song, doesn’t it?). I’ll break it down by each section mentioned:

Six Pictures

You have six pictures to make an ideal impression on your would-be prospect. I’ve seen both my friend’s profiles and some acquaintances. If you don’t like taking pictures either befriend (or pay) for professional photography headshots. If you’re crafty (or gutsy like I was), you can have someone take them for you and take a chance. For my recommendations you should have a split, three photos of you: One clear headshot, one full body shot, and one action shot (pick your ideal activity: climbing, racing, dancing, etc.) The other three, should showcase your personality/interests: Do you like dogs, have a specific passion, have an “urge” to travel (which is very common in dating apps)?

Once you pick those photos you can put it in order, now there’s another three ways you can break this out:

  1. Treat your dating profile like a page from your life story, infographic style and easy to follow, top to bottom
  2. While creating PR highlights about yourself in between the snippet

Three Answer Prompts

English majors, Hinge will make you shine so hard, it’s not even funny (maybe even OkCupid), very few know how to entertain those with a tap of the keyboard. In any event, if you’re a man of few words, use your concise language effectively. My recommendations are: Two Truths/One Lie (if you live an interesting life, are a good liar, entertaining storyteller, or all of the above), I’m looking for (you can be as blunt or witty, e.g. I like tongue and cheeks…. tongue twisters and baby cheeks to pinch, you pervert), & Ideal first date (to set the tone of the first encounter).

Seven Virtues

This is your personal/impersonal background. You don’t have to give out your life story like a business card, of the seven, I would say: Work, Job Title, and Education Level are the most important. A tie for forth is Religious Beliefs/Politics, if that truly matters to you.

Eight Vitals

These are your sports stats, get ready to flex (or not flex) your biological prowess. As for the important ones in this list: Gender, Age, Height, Ethnicity, Family Plans and Location. If you’re concerned about stalking safety (yes ladies, it happens to guys as well), then change your Location setting to what’s reasonable and within the area you’d like to be. Just note, if you place yourself into some “perceived rich metropolitan area” you could be cat fishing those along, who might be looking for a lifestyle that doesn’t equate to your standards. 

My Four Vice

This particular section is all about which vices resonate or deal break the entire experience. Do you sip, get lit, hit the bong, or go off the grid?

Instagram feed Syncing is optional. If you decide to sync it, think of it like your first pictures but people will be able to “Hinge comment or  heart like” (I’ll explain this in a bit). your photos via IG (up to the most recent 27 entries). Again, think of these recent entries as part of “What’s going on in my Social Media life recently?”


Now that your profile is set you’re ready to engage. When you encounter a profile, you’ll see their name in the top left corner. And you’ll begin to notice the choices people make on their photos, prompts, and etc. The heart icons enable you to “like” a specific part of that profile (why I encouraged optimizing your profile from the beginning). While scrolling top-bottom you’ll see a pink-red ‘X’ notating you can outright reject the current profile (a swipe left in Tinder/OkCupid land) and movie onto the next. If you did your due diligence, once you like this person and they review your awesome profile, they’ll like you back and “maybe comment'” about whatever picture or content you wrote about.

Like most dating websites, there are stereotypes both regionally/nationally/globally about genders. For instance,  women on dating apps “love to travel” (I get it, you have not only disposable income but you’d also like to explore a buffet of men and destinations before settling down, men feel the same way). Whereas guys love to “Rock Climb, go Camping, Racing, or “Raving.” etc. Pick your poison and if you want to make it a drinking game, play dating app bingo and see how many stereotypes you come across. Also note, didn’t realize women we’re already ahead of the curve, case in point (however the insecurities of putting dating effort into the app, definitely hit her hard) as well as a few others who came into this realization.

Overall, you get what you put into any experience and dating apps are no exception to this rule. Sure, there are some things you might want to hold back on your first few dates. However over time people will eventually see if you’re worthwhile or not, which I stumbled upon content creator George Bruno and his timely video here, said this in his script “Women marry a lifestyle, a man marries a body.” 

This really hit close to home because as I get older, I do fear in some respects that could be a possibility. And with the advent of Social Media, more and more people are “conforming/settling” for a specific lifestyle, I wonder why that may be the case? Side note aside, Hinge as a dating app (like everything else in the market) gives you an opportunity to meet new people. Some of you are expecting 100% effectiveness with these tips, unfortunately it may not work for some of you at all. I’m merely sharing my experience because I had to learn the hard way, there were no resources for Asian-American males and the things that were taught to me, didn’t apply (or I didn’t have the “model look” to pull it off like some of my peers LOL).  

All I do hope is whether it’s this holiday season, you’re trying to get an extra ‘snack’ to stay warm with or are truly looking for something meaningful. I hope these few tidbits can help you one step closer in your journey to happiness. Merry Christmahanukwanzaa to all and The Relationship Podcast will be ready to ring in 2019 with a brand new season! Thank you for the support as always and take care, the only single guy on the panel signing off!

-R.M. 2018 DAT TRP



Shuffle Around Life: Chapter 3 (7, 6, 5), Dating App Tips Series: OkCupid and More

Here’s my explanation for this long-overdue Chapter, I wanted to create a bit more coherence between posts (beyond Cartomancy and the general theme of top, middle, and bottom) and introduce a small mini series called Dating App Tips The RelationshiPodcast Series (or DAT TRP)

This series is a build up to the Dating Project I mentioned a few episodes back and I’ll start with a semi-popular and somewhat relevant app of today, OkCupid. There are many reviews of this app, you can read Mashable’s, Ask Men’s, or Dating Scout’s version. However my review is different because I will share with you the few tips you need to have the most optimal experience. One other thing to keep in mind, this is coming from a heterosexual minority (Asian-American) male so your experience and mileage may vary.

Let’s get started!

Unlike Tinder and Bumble what sets this specific app apart is the long form survey questionnaires. People get real lazy and from my experience if a woman really appreciates your “aesthetic” chances are she didn’t read your profile for jack shit. So you’re probably gonna ask, “How can I get my own bae?” Welp, here are some best practices and specific questions to look out for:

  1. Be yourself (write your profile as if you had a girlfriend/wife).
    1. I know this shit sounds weird but when I first created my profile a long time ago, I thought about it like a “Marketer/Youtube Clickbait writer.” Trust me it works, the more genuine your tone and candor you provide. Your personality shines bright like a diamond and the chances you’ll be matched with someone will increase (even if you feel like your ugly as sin itself).
  2. Watch out for specific questions that could indicate incompatibility based on your lifestyle and core values
    1. Ethnic/Race preference Question: Probably the biggest indicator (if your ideal mate) likes to stick with their own kind. Even OkCupid Christian Rudder reference’s in his book Cataclysm, that this question is supposed to indicate some sliding scale of Racial preferences. A 95% of the woman I swiped on thankfully answered in this manner:
      1. Would you Strongly prefer to date someone of your own skin color/racial background?
        1. You answer: Whatever
        2. She answers: No
          1. There are a few profiles I encountered that say “Yes” and majority of those were Caucasian and Asian women (no big surprises there given our previous podcast episodes and historical data).
      2. Would you ever consider ending a relationship because a parent, family, member or close friend didn’t approve of your partner in terms of attractiveness, race, nationality, gender, age, or other factors beyond their control?
        1. You answer: Whatever
        2. She answers: No
      3. If you were going to have a child would you want the other parent to be of the same ethnicity as you?
        1. You answer: Whatever
        2. She answers: No
          1. Fun fact, if she says “Yes” and you’re not her ethnicity, well I feel bad for you son because…. 99 problems but a kid ain’t one. *Jay-Z voice*
    2. Money Question(s): Again, another dead giveaway. People usually don’t put in the work to answer these for yourself but you should (and for good reason). If you don’t want a “Gold Digger” than anything that shows she values money potential you might, have a large incompatibility issue in the long run. Furthermore, I would stress that a whopping 98% of the profiles I’ve encountered answered these questions in the same way regardless of ethnicity, that I swiped on (shocking I know) and here are the two questions and their affiliated responses:
      1. Is your ideal match well-off financially or at the very least someone who has high income potential?
        1. You Answer: Whatever
        2. She Answers: Yes it’s somewhat important
          1. If she answers “Yes it’s very important,” now I ain’t saying she a gold digger but..
      2. How important is money/wealth for you in a match?
        1. You Answer: Whatever
        2. She Answers: Yes, it’s somewhat important.
          1. …she ain’t a messing…
      3. Would you date someone who was in considerable debt?
        1. You Answer: Whatever
        2. She Answers: No
          1. …With a (Broke/Student Loan heavy/no new BMW type) ninja. However if she ever says, “Yes, its not a problem for me.” that’s wifey material right there (hard to come by).
      4. How would you feel if your significant other made more money than you?
        1. You Answer: Whatever
        2. She Answers: Very Comfortable
          1. Fun fact on this one, I NEVER see any ladies say “Very Uncomfortable.” Given the whole movement in 2018 for dating equality, there are some things that will stay the same till the end of time.
      5. Do you believe money can buy happiness?
        1. You Answer: Whatever
        2. She Answers: Yes
          1. If she answers yes (in addition to the above questions), then I hope your pockets are deeper than the Mariana trenches, cause that child/lifestyle support money is serious in 2018
    3. Hygiene (Biological/Lifestyle) Question(s): You’re probably thinking, damn Ryan I can’t pick up a woman if I don’t wash my balls religiously or brush my teeth twice a day. You can thank your stars Jimmy, this isn’t that much of a deal breaker. Granted I can make the case, that most people have some standard of basic hygiene and the arguments for lack of hygiene is purely for lifestyle optimization (not washing their hair everyday, is a ‘dirtbag’ (rock climber), or HLA (Human Leikocyte Antigens) incompatibility). In my sample size, 60% of the women I swiped on answered the question and provided these responses:
      1. How important is it to you that your partner smell good?
        1. You answer: Whatever
        2. She answers: Important-ish or Less important than you think
          1. If she says “I just don’t care at all” may your crusty balls be forever cherished.
    4. Lifestyle: This isn’t lumped with hygiene because you can avoid the restroom for a few weeks and still be a rational (and somewhat ethnical) human being. However do note, depending on what you’re personally gunning for you may want to focus on certain questions and de-prioritize the rest. Here are the questions and their respective responses, keep in mind 70% of the women, I swiped on answered in this manner:
      1. Would you date someone who still lives with their parents?
        1. You answer: Whatever
        2. She answers: No
          1. Another fun tidbit, if she says “Yes” and you’re living in a very expensive part of the country *COUGH* San Francisco Bay Area/Manhattan/Hollywood*. Good luck, trying to convince her otherwise.
      2. Would you consider having an open relationship (i.e., one where you can see other people)?
        1. You answer: Whatever
        2. She answers: No
          1. One of the things I learned from past dates is if she says “Yes,” then you shouldn’t hold your breathe on commitment quality, just saying (and this is beyond the “Dating Phase.”) as well.
      3. It’s your first date. Do you split the bill, pay the whole bill, have them pay the whole bill?
        1. You answer: Whatever
        2. She answers: Split the bill or It doesn’t matter to me.
          1. If she answers “Have them pay the whole bill.” then you know what to do chief.
      4. Would you consider sleeping on a first date?
        1. You answer: Whatever
        2. She answers: No
          1. If she says yes and she’s also down to hook-up, then make sure to stay equipped.
      5. About how long do you want your next relationship to last?
        1. You answer: Whatever
        2. She answers: Several years or The rest of my life
          1. I never seen the answer “One night” usually few months to a year is common.
      6. Has anyone ever accused you of being “high maintenance”?
        1. You answer: Whatver
        2. She answers: No
          1. If she answers “Yes” in addition to the financial questions again don’t be surprised…
  3. Read their profile and find common ground between you two
    1. No surprises there but there’s some amount of work you need to put in.

Other questions to look out for and determine good compatibility not just for dates but long-term relationship potential are:

  • How many children would you ideally like to have?
  • Is it ok for a woman to ask a man out on a date?
  • Would you consider being in a relationship with someone who has had homosexual sex?
  • Does hanging out in an empty field, in the middle of no where, at 2am to watch a meteor shower sound like fun to you
  • Are you still in love with one or more of your former partners?
  • Which of the following do you find to be the most liberating?
  • How many countries have you visited?
  • Have you stayed friends with most of your ex-boyfriends/ex-girlfriends?
  • Do you have an ex that you would really like to date again?
  • Are you flaky (i.e. cancel plans at the last minute)?
  • Can you cook?
  • Do you believe regular sex is necessary in maintaining a healthy relationship?
  • Do you ever ghost someone (cut off contact without warning) after meeting in person?

These questions are a supplemental litmus to determine how adventurous, reliable, and/or “not ready for a relationship material these prospects” are. You can observe on the one’s I highlighted here to determine, the ideal people I’d like to build a relationship. However if you really want to take the bare bones optimal approach use the questions I bolded as strong indicators of overall compatibility, that might help you in your search. Hope this helps and look out for an upcoming Podcast Episode on Double Standards and the next app I’ll review in the DAT TRP series.

Shuffle Around Life: Chapter 2, Another one bites the dust, J-7-Q

It’s super early in the morning and I cannot fall asleep due to this weird episode of insomnia and sickness. After having a crazy week of work and getting super sick (cabin fever and all), I’m ready to retreat into my shell and never come out for the rest of the month. However I don’t have the luxury to do so and it some cases, I truly wish I did.

Taking one step forward and three steps back seems to feel like the appropriate cadence, at least the peanut gallery always reminds me of what little progress I make. When I began shuffling the cards, I was really hoping for a particular trio to come around. But with anything in life, you can only leave it to chance. Many people who are driven, rarely ever believe in the value of luck attributing to their success. It’s working effectively and consistently, day in and day out, to strive for something better (even if it’s slightly better). One unspoken tool successful people forget to mention is, the unconditional love and support of those around them, enabling them to succeed and push through the barriers when the going gets tough.

This was the first time in a while, I felt very alone, not knowing what to do next. I usually have a contingency for almost everything and this is the first time I felt so ill-prepared. You can talk to anyone and ask for their advice. As they lend you their ear, shoulder, time, and attention. When you open yourself up, you also increase the likelihood of being judged (by an apathetic party). In the end you have no choice but to do it on your own because you’re the only one with the scope of the full picture. There was so much questioning I did this week about my future and where I want to be. I haven’t felt content, never have been for a very long time. Therefore one of my main priorities that I’ll be focusing on from here on out, is to finally solidify my own support system and then go on from there.

Now for the cards:

Jack of Clubs: According to the internet and the history of cards, the jack (also known as the knave) is the lowest ranking court card. If we we’re to go by suit, I’m barely above diamonds. This week, I definitely feel like a knave.

Seven of Clubs: Now, with this card there’s many interpretations (and I just realized) in some cases people use playing cards as supplements to a tarot reading/cartomancy. However without getting too spiritual, most people say it’s a card of worry or difficult situations. Again this week is definitely a reflection of that.

Queen of Diamonds: Apparently again the interpretation of this card is of a wealthy woman figure but would bring danger into my life. As they say, more money and more problems but thankfully I don’t know anyone who would fit this description currently in my life.

I hope next week’s shuffle will be better once everything levels off but until the meantime, this is the best that I can do and provide. May the RNG be in my favor sooner or rather than later.







Shuffle Around Life: Chapter 1, begin to re-shuffle priorities, 7-7-8

This series was meant to replace The Single Life column for two reasons:

  1. I’m not single anymore, so there’s no point in continuing forward.
  2. Neither John nor Andrey is single either and would have any relevance with maintaining such a column.


With this in mind the new setup and approach with this column is like a deck of cards sans Joker Card(s). I’ll shuffle around the deck and point out the highs, lows, and everything in between with regards to what’s going on in my life.. I’m toying with the idea if I should actually shuffle a deck of cards and see what is the top, bottom and middle card drawn from the deck. There’s 52 cards and 52 weeks, so maybe this can reflect every three weeks?

The cards in display are as follows:












Highs, 7 of Spades; Spades historically have been the suit to beat. The seven isn’t too high but it isn’t too low either. Ever since starting this podcast and having this escalated amount of responsibility it feels as though time has accelerated tremendously. Unlike many of my peers, within our age cohort most of us are (or at least presumably) ready to settle down and really get your shit together.

Lows, 8 of Clubs; The suit of clubs is an interesting bunch. This isn’t the king or a bottom card like the 2, however in my life at the moment, my energy feels very depleted. In reflection, as noted by many of my co-workers, it follows in a three of a kind. Someone’s getting engaged, married, or pregnant. In my life, someone has gotten engaged, invited me to my first baby shower, and has gotten married. Furthermore, it makes me wonder when the time comes to have a family of my own, will I ever be ready to step up and become a father?

In Between, 7 of Diamonds; If you played “Big two aka Pusoy Dos aka an Asian Gambling game,” my middle school self would be ecstatic when the suits are ordered (clubs, spades, hearts, diamonds). Perhaps I had it all wrong in that the correct suit priority was (Diamonds, Clubs, Hearts, Spades)? One of the biggest skillsets to have in adulthood is shifting priorities, certain people, projects, and hours in the day will be allotted to take precedence over everything else. A year ago today, my life was extremely different. I had a more robust social life… A mid-size social circle, plenty of activities I participated in, and dating was like a box of chocolates because you never know what you’re going to get.

Thanks for reading this very rough, first post but I’m still creatively figuring out how to present everything.


Final Chapter of TRP Single Life: Execution, Timing, and Luck; Same Woman, Three Dates (Dates #11-13):

“You have everything I want in a person but… I’m just not feeling it and I don’t know what’s wrong with me…”

Final Chapter Author’s Note: These series of dates happened a while back (before I got into a relationship) so this is sort of a recap of what happened prior and what’s to come with this column. Anyway hope you enjoy it!

Execution, Timing, and Luck are necessary to lead you into the next door of opportunity.


Everything in life is a combination of three things: Timing, Execution, and Luck

The execution piece is obvious, it’s probably the only thing you have complete control over. Whereas Timing and Luck are the two other elements you will never be able to control. You’re also probably wondering why I’m not lumping timing with luck because although they’re obviously intertwined, it’s quite different when it comes to being variables within the success of any relationship.


Date #11: Timing


Like all things in life, you have to be at the right place at the right time. However in terms of dating apps, sometimes a glass of scotch and perusing dating app profiles is a better way to get the weekend festivities started after a long work week. I was at profile number 50 and I was ready to call it quits. Finally she appeared, her name read Mizunara, “Worked in the City, active, and had a nice smile to boot.” *Clicks Accept*

Sipping on scotch while watching Netflix, ten minutes have elapsed and then the pop up notification came “Mizunara has accepted the match, please begin to chat.” As usual, one message became two, four, and you already know the drill….So we meet at this bar on a hill (the rhyme wasn’t intentional). Simple digs and there was a party there before us, she then explicitly stated, “If this doesn’t work out at least we have good drinks.” Our conversations weaved in out, between the yesteryears of college midterms to  future aspirations. As we paid the check, I asked her did she wanted to proceed. She nodded, waited for the check, took my arm and off we went for dinner.

On the way we stopped at a cross walk and made out. It was clear, the night wasn’t over yet. We had food, enjoyed conversation and I’ll leave the rest of the imagination to you all… After our fun, we made plans to see each other in a week and a half.


Date #12: Execution


We rendezvous’d at a mid-point within the city. Gave each other an embrace and a single kiss as anyone dating would, especially when they rekindle their passion for one another for that fleeting moment. Having been a very simple date, we decided to keep going with the theme and went to a beer and wine specialty bar. As usual, time elapsed and we continued enjoying each other’s time and conversation. However as my previous experience (and slight jadedness has taught me), sometimes if things are too good to be true…Then it is. I’m already 2/2 and as we kept talking, I was looking for the x variable, the thing that’ll throw a wrench in this whole experience. I know I shouldn’t be thinking like that but I knew at some point it will come up. She then mentioned, the x variable, “I hadn’t been in a relationship in a long while and I don’t know if I’ll ever settle…”

You see, she had everything else covered. Stable career, active, reasonably attractive, and etc. However when people start sharing they don’t know if they will ever settle. There’s this restlessness that settles in (at least it did for me), it’s very intuitive and a huge red flag for me. Psychic abilities aside, I don’t know if I’m willing to risk that, however there results were laid out to bare our final date…


Date #13: Luck


A week has gone by since the last date, and the dreaded text finally came on a busy Thursday morning at work


Her: Hey

Me: What’s up?

Her: Can we meet up and talk later tonight?

Me: Sure…


When we met up with one another, the hug (was half assed, butt sticking out using one arm) and the body language became distant. I knew right at that moment, regardless of what plans we “initially discussed” via text wasn’t going to come to fruition. She told me up front,  she wasn’t feeling “the chemistry.” My luck had ran out and this person wasn’t the one for me. At the time I felt completely rejected like any other human being, but if it wasn’t already noticeable I had learn to adapt (and dispose) whatever connection I had with this person like a useless folder of pictures of your exes. Dragging them into the Recycle Bin on a PC, with intent of permanent deletion and memory lapse.

You see, in the human language of the words “Dating chemistry,” its a culmination of emotional, physical, sexual, and spiritual attraction all wrapped up into one. If your partner (man or woman) cannot see themselves, at some point doing anything of those things (for a long period of time) it’s a wrap for that possibility. At times it feels like a “cop out response” easy to serve without remorse. More often than not, it’s the woman who will determine the chemistry barometer. As a guy (or the pursuer if you’re LGBT), your sole task is to uncover the catalyst of that chemistry and decide for yourself if it’s worth maintaining in the long-run.

Throughout this series, after reflection I realized there was a lot of confirmation on my end both in long-term core values and daily relationship nuances. For the first time in a long-term, before getting into my current relationship. I have some lessons, I would like to share from this experience. Hopefully you can learn from example (instead of experiencing them like I did), in order to find more fulfilling relationships.

  1. Appreciate Someone’s Identity: Don’t think of them as another “name” in your cell phone.
  2. Good on paper, doesn’t mean good for compatibility: We all have “ideal mates” but realize they’re not perfect but always a work in progress.
  3. Shoot for the moon but have a parachute in handy: You can climb the highest mountains but if they’re not willing to summit with you, re-evaluate.
  4. Everyone is searching for love: It can get complicated but the more honest you are with your search the easier it is to find someone more compatible.
  5. A kiss isn’t always meaningful: Some people hand them out like business cards but your individual actions beyond the kiss mean much more in the long-run.
  6. Substance Influence Dating isn’t recommended: You can argue for it’s shortcomings (or miraculous opportunities) but in the long-term it doesn’t really pan out for most.
  7. Never double-book yourself: It’s not sustainable and you won’t value the people you spend your time with (personal and platonic).
  8. Don’t over communicate before your first date: Whether it’s sending 200 messages on a dating app or talking 2 hours a day for two weeks. It’s setting the wrong expectations.
  9. Always work towards the middle ground: People will take advantage (or remain oblivious) of how unfair it feels at any moment when things are imbalanced. You and your potential partner need to always vocalize, reflect, and respect each other’s differences. The sum of your experiences are entirely different from their own. Learn how to leverage and intertwine this knowledge for a better foundation.
  10. Realize all the wrong relationships were meant for “The Right One”: We can debate till the end of time people’s definitions of soulmates: Astrological, Atheistic, Christian, and etc. At the end of the day, when you (and hopefully your partner) realize how much the other brings to the table. You’ll soon see that is the reason why they remain (and continue to flourish) in your life.

… I am grateful to be developing a wonderful relationship with a very sweet (and independent) lady. However this is just the beginning and now I begin to shuffle things around in preparation for things to come.

Thanks for reading this series and hope you continue to in the next chapter of my relationship life!



Date #10: Lots of Messages= My Sassy and Straightshooter of a Date

Author’s Note: Sorry for the Long Delay given work and life but now, we’re back on the momentum and grind…


Lots of Messages, from our emails, to our dating inboxes we’re ridden with all kinds of stuff. This date was no different and like things it started on a good foot and eventually let to nothingness. In the beginning, like any other first dating app impression of one another, we slowly sized each other up.

She shared a bit of her current background and aspirations of the future, as I did with mine. However as time went on, I noticed our exchange became quite enormous. What started as a few messages, led to 50, then a 100, and afterwards it became such an egregious number to where I literally said, “Why don’t we just talk on the phone/facetime given all of exchanges?…”It’ll be quicker and there’s less typing involved.”

For many people, who know me IRL and heard me referenced this Ad-Nauseum before within our podcast episodes. I’m not a big texter by any means, I get that it’s the preferred mode of communication but I have serious hang up about it.

*Author’s side Rant Starts*

For one, unless you meet through a dating app you typically don’t really know the person until you’re in proximity (face to face). Second, a lot of times because text messaging is similar to email you can get really distracted easily (another “date potential,” other friends, family, etc.) Finally, we’re not robots (at least I’d hope, I didn’t date any in disguise yet?) and if you don’t want me to communicate with you via text as we sit/stand next to one another, then please let’s be humans and actually verbally converse. I had dated someone who gave their two cents on the issue, “A Phone Call in my generational cohort, is like getting a direct request from the Principal’s Office, as if you were going to get Expelled.” Are you fucking kidding me? This dramatic exaggeration is a major turn-off which is why I try my best to proactively filter those who are in love with this form of communication. The only thing useful with this modern medium is to slide into those DMs before you slide into one’s underwear.

*Author’s side Rant Ends*

Once our phone conversation began, they went even longer, she was definitely a ‘chatty cathy’ but I appreciate that because then I don’t have to talk as much as one would expect. After several days, we finally met up at a wine bar after work downtown. It was extremely filled to the brim on a Thursday evening, I didn’t imagine it would be this packed but then again this is San Francisco after all. She looked pretty cute in her mint green dress and heels. I wore a simple business casual outfit with some oxfords to at least put forth some type of effort. She constantly reminded me of her “Boughetto” (Bougie and Ghetto, for the uninformed) behavior and yet when we had a flight of wine, she wasn’t too familiar with the process.

I then, explained to her the process and she was baffled because she didn’t expect someone like me to have such  a refined palate. Looks are deceiving and this isn’t the first time it has happened, I guess when you look (and feel) a bit rugged you don’t give off the clean cut demeanor to certain folks. Anyway, we ended up walking around town until she wanted pizza from a certain area. I told her gently, I wasn’t really feeling but she insisted I got a bad batch. After getting the pizza (and trying it for a second time), I still wasn’t impressed and she was disappointed. During this time, I already had slight inclination (two hours into the date) it wasn’t going to work out.

You see comfort with physical touch is critical for a guy. I don’t care what anyone says about their preference, but if someone is not willing to be close whether it’s holding hands, hugging, or even hinting at a kiss. There’s no future for the both of you, just drop it. It’s a simple litmus test really and as a guy you don’t have to be “aggressive” to find out, even the distance between you two as you walk should let you know what’s up. In my case, by the time we were lounging around the bookstore, I knew it was time for the fairy tale to end. I did the gentlemanly thing and waited for her Uber to pick her up before leaving (I asked her texted me to let me know she got home alright at least). After giving her a hug and seeing the Uber drive off, I realized you don’t need to talk to someone for four weeks to find out your incompatible.

As I got home, she texted (instead of called) to inform me she got home. She then mentioned, what I expected and wanted to stay friends but I refused. The reason is, even though I wanted to, for some people like myself it’s weird meeting someone, knowing you were involved with them at some point and acknowledging they’re being intimate with someone other than you. I can commend the people who can stay friends with their exes/ex-dates after a fall out, but let’s face it a lot of the times, it’s a fall back option. It’s something I also used to do, till I realized one day it wouldn’t be fair for the next person.

So long many message lady, you probably found someone who can appreciate your “Boughetto” habits. The search continues…

Date 8 & 9: Different Women, Same Day: Rolling Cliffs and Lost in Translation



Her: “So, what is a triple threat?”

Me: “It’s when you’re good at three different things?”

Her: “I won’t give you my number, but I’ll give you my address to pick me up?”

Me: “Uhh ok????? *confused by logic*”

I know so you’re probably wondering, how in the hell did this happen?

Let me start off first by saying woman #2 mentioned in quotes, was supposed to be a delayed date for the following week but insisted I meet her the same saturday as woman #1 except in the evening… I’ll get in to that. Let’s start off with the first woman…

I met her on a different dating app and so far, like all first impressions I thought she was pretty cute. Slim, long hair, dark brown eyes, rosy cheeks, the whole nine. I figured why not, give it a shot, after a few messages here and there I noticed she wasn’t from around here. So we planned for a hiking ‘date’ the only reason why I started putting ‘date’ in subtle quotes are because at this point of time, the way ‘dates’ were discussed or planned became very ambiguous. I would say a date to the people I corresponded with, they would say ‘hang out.’ Someone else doesn’t say date, they just say ‘let’s meet and see what happens?’

It was at this junction that I began to believe, are first dates really a thing of the past? (hint: this may be a future episode or article). Anyway, I didn’t let the semantics get the best of me, so I planned on picking her up from one of the station and then we would carpool to our hiking destination. As soon as I drove up the curb, “I saw her except, she looked slightly different from the filters.” (not catfishes but definitely not as rosy). So we talked about our mornings and finally got to the trailhead. It was a mainstream spot, where the ocean met the sky. As we were talking, there was a crossroads and I asked her if she would be up for the challenge. I even warned her, it may be difficult to getting down, she didn’t mind.

As we went began our ascent, I noticed that she kept going behind me despite the trail and coastline being wider than five linebackers. It felt kinda weird and I even told her to go on the side, so I can talk to her and not feel like we’re scanning the Amazonian jungle and covering my flanks. We reached the fake summit and she then responded, it’s getting pretty tough. I told her we can back out, but she insisted and so up we went up the tiny dried up waterfall trail. As we climbed, I noticed she began to slip and I tried giving her some advice (not to ‘mansplain’ but because I had experience leading hikes; if a woman gave me advice and I was inexperienced I would’ve listened). She didn’t listen and her stubbornness began to show, it was admirable but became mildly annoying whenever she screamed and asked why she kept slipping.  We finally managed to climb to the top to see the nice view with a bench peeking out. “I would’ve preferred doing this on my own,” as I thought to myself. No matter, I was already in the moment and there was no escaping the present reality.

At this time of the date, I knew it wasn’t going to work out but I kept going because I didn’t wanna waste my time and feel like I did all of this for nothing. So I did my best to keep the conversation going while we went downhill. Now this is the frustrating part, I constantly reminded her to not rush and just take it slow as we treaded downhill. Did she listen? Nope, she just said kept doing her thing and she almost rolled down the hill like a rogue boulder off the cliff. After another 40 minutes passing we finished our hike and got some food before I dropped her off at the station. I had to take this a hard pass on this one and move onward…


The second woman, I only spoke with for several days and a lot of the times I like to space things out to avoid any schedule conflicts (like this one that occurred). She insisted on meeting up later on this evening (mind you, I just came back from my mid-afternoon date). So I was mulling it over and I said to myself, “Screw it, what’s the worst that can happen, right?” Spoke too soon, spoke too soon… After exchanging text for the next 40 minutes, I asked her, let’s just exchange numbers maybe FaceTime and see what happens? She then replied, ” I won’t give you my number, but I’ll give you my address to pick me up for a face to face date?”

Huh??? What is this logic??!?!?!? I would honestly think giving a number is much safer than giving home address? Uhh, I thought again for a second time, thinking to myself. “Nah, she can’t be this dense… right?” Wrong again…. oh so very wrong. At this point, as a single guy on a saturday night, if you’re left with Netflix, swiping more potential dates, or drinking yourself to sleep. This attempt of entertaining myself, is probably the best decision I could ever make. I take a shower, hop into my car and pick her up at her place later that evening. So, I’m waiting there and I’m literally the only car with blinking emergency lights on, she then messages me via dating app and says, “Where are you?” I replied, “I’m the only car on the block with blinking lights.” She says she doesn’t see me (seriously, is this going to be an episode of catfish?) I said, “Unless you’re pranking me, I’m at the front of your place.”

She finally comes out and as she entered the car, I remember the power of “MySpace angles.” She looked alright but definitely not the same perspective. Anyway, we got some food and as entered we did the usual “back and form interview routine.” As this point of the story you can probably already tell this wasn’t going anywhere. I’m  trying to constantly improvise my own ‘dating algorithm’ and automating it with my canned responses. This was the beginning of the decline, all the “moments”  began to fade away like defragging a computer hard drive. I realized,  as we grow older many of us use “self love” as an excuse to be obsessively selfish and guarded. The one thing, I have to ask is, “Where does one draw this line?”

We like to bring ourselves up to the highest peak imagineable and unless someone passes our “relationship barometer” we won’t even bother giving them a ladder (or ledge) to hoist themselves if they’re struggling to reach the summit (fall off bitches!). I hear this all the time, through dates/co-workers/people on the street about the struggle of finding good “dates/partners/relationships/etc.” Feminine women do not have this burden as a relationship decision maker (straight or LGBT). The obvious answer is to look at yourself and improve in the areas of weakness (especially if you’re a guy), especially if you suck at life. An alternative would be is to embrace singledom for the rest of your life because nobody else can do it better than yourself. In the meantime, I’ll keep dating (and entertaining) you all until I finally get sick of it.

The Single Life: Date #7, Mission Analytical

Analyzing any situation good or bad, can get out of control even in beautiful surroundings..

Analytical tendencies and mistakes, I made a terrible one and took a coworker’s advice because this was the week of overwhelming dates and opportunities and this date could’ve been better but before I get to this point, let’s start from the beginning of the week..

My Date: Let’s go to this place in the Mission, they have tasty drinks….

Co-worker: You should go to your date absurdly drunk, it’s probably fun and you’ll experience something different for a change?


At this period, I already experienced in one week a streak of dates ranging from impromptu photography,  cheesy flower antics, and political charged discussion and now tonight’s date. This entire week, I was texting this person and three others to fill up the next couple of weeks. I was on a roll, it wasn’t an entirely positive one but I made it happen somehow.

Exchanged messages with this one lady, who’s love for bacon and data knows no boundaries. We had good “text chemistry” but the real deal had to occur within a week and a half. When you get back into dating, especially this 2018 version everyone knows and loves, the lines to really blur and the timelines become unexpectedly complicated. You see unlike project management, where its expected to have a “moving deadline,” dating wise one of the biggest struggles is this idea of the “stake in the ground” commitment of the first date.

Surrounded by technology and some of the most influential companies in the world, you’d think we would find a solution to this problem. That isn’t the case and as each day and text went by, my fatigue began to show. In my current career  the hours are demanding and technical challenges are always an expectation. My day to day can easily change in a blink of an eye unlike most roles. However I crave stability, predictability and the occasional good morning text that someone would give just to add a little extra perk. After the busy workweek was over (thursday night, is an early start for most professionals and young adults), things got a little out of hand at a bar we frequented within the downtown area. One drink, after another, turned into four glasses of truth serum.

One by one, my co-workers and friends kept asking me the usual questions and banter,

“How was the last date?”

“What happened with xyz?”

*insert relevant dating cliches and platitudes here*

My mind began to wander and as I received the last text from my date tonight, “Can’t wait to see you tonight.” I asked if any of my co-workers wanted to come with me pre-dinner before meeting up with this person. One of them accepted and we conversed about nuances of life and the complexities of dating. I paid my share, gave my friend a hug, and off I went to this analytical lady. I entered the bar and it was a familiar scene, a mix of cardigans, tech hoodies, and handlebar mustaches. My black horn rimmed glasses, didn’t help painting the cliche portrait but I had to fit in somehow. As, I stood in my corner in a semi-drunken stupor, someone tapped me behind the shoulder.

She was petite, had her hair up, also with black horned rim glasses and a cute smile (it was my date for the night). Now painfully, this is where things get a bit more hazy than expected. We had several more drinks and exchanged the usual “dating interview dialogue.” However one thing that stuck out the most, was her simple words of, “You know, I have a keen sense of situational awareness as well…”

Now, this simple phrase wouldn’t bother me too much but it was at that time, I realized I don’t know why I even accepted the date in the first place. She was analyzing me as much as my inebriated self could muster some form of analysis. The body language, the levels of comfort, and of course the possibilities to go beyond the first night of sex. That lasting impression was made and it sealed my fate… That I was gonna go home alone that night.

Sure, she was great on paper and we had good conversation but this was one of those convenient and nothing better to do on a Thursday moments. I reflect back on this date, nothing really stood out, other than our in-person chemistry was lacking and my drunken self was disappointed when she called the night off short (45 minutes into it). Perhaps this is why, I decided to liquor myself up prior to meeting her, it served as a safeguard in case of disappointment. Sure enough, this strategy justified itself (in an aha-esque fashion) serving as a self-fulfilling prophecy (I’m a psychic, bitches).

Companionship and ease of conversation is probably one of the things I miss most, when it comes to being in a relationship.  Everyone puts up some sort of facade up, no matter how “real or one hunnid/100”  one claims to be. We like to project the best version of ourselves, even when we’re barely keeping it together deep down inside. As I walked home, I began seriously evaluating my dating filters, whether or not they needed some serious adjustments. Serial dating, really isn’t my thing, but one of the biggest mistakes I recently with someone I dated for a while, was putting all my eggs in one basket. It is the sole reason why I continue “stack/stagger” dating in this process because I’m sure all my prospects are doing the same for me. I haven’t found anyone worth investing from the jump and I have yet to meet woman that can securely say, “You’re the only one I’m dating.” And give me a reason, to purge all my apps and prospects for good. An idealistic sentiment, that one could only hope and dream of.

This old school mentality of dating, it was much more simple back then. I wish this generation wasn’t so infatuated with FOMO and the “grass is always greener” ideologies. Until that ideal woman comes into my life, the only thing I can do is: pivot, iterate, and find someone who embodies and smashes my bar of standards to smithereens.

The Single Life: Dates 5 & 6: Same Woman: Cheesy Flower Bowl Antics

1st Date Leftovers…

Cheesy and wine glasses, almost a month back in to the dating game and I’m getting sick of the stuffiness. At this point, nothing should surprise me and my expectations were slowly dwindling. This lovely lady is a software engineer but we didn’t have an exciting conversation the first time we chatted via dating app. However somehow we managed to meet up for a drinks and by some weird coincidence she was fine with the same place, I’ve met someone else at before (not intentional but it worked out that way). I was running a bit late because I had to work Overtime and I was nearly exhausted by the time I got to the date spot.

So I can’t believe, I got a flower bowl just to drink soup and everything spills over.

The place was blasting with music and all I saw was a woman with long hair, a peach dress and a quiet demeanor. I thought to myself, “This date is probably gonna get awkward, real quick.” I introduced myself and we gave each other an awkward handshake/hug (I didn’t know what she was trying to go for). As we sat down we ordered a few orders, one of them being a couple of toasted burrata pieces and our drinks. Within 30 minutes it went down with the cliche order of operations…


Me: So, how was your day?
Her: Good, not too much work and you? *eats quietly*
Me: It was exhausting but I’m glad it was over, how do you like burrata?
Her: Good, not bad at all. *sips quietly*
Me: …Ok, do you like your wine?
Her: It’s ok, I just ordered it because I couldn’t decide… *continues to sip quietly*


I was ready to throw in the towel. She then exclaimed, “I would talk more but it’s so loud so I’m afraid you can’t hear me.” I told her, “Wanna leave early and try for round two, given the circumstances?” During this time she explained about friends visiting, her work, and her limited time. I was for certain this was it but then she replied, “Yes, that would be great. I’ll let you know when I’m free next week.”

I covered the tab and then escorted her to her Uber. Gave her a proper hug and she went on her way, Date 1 was over.


Next week arrived and we were planning for Date 2, a quieter and more intimate venue. They didn’t have reservations but it ended up being a walk-in spot. She got there earlier than I did because it was the weekend and she just finished shopping with her friends. We ordered a few flights of wine and over the course of the evening the alcohol caught up to us, we became a bit more flirty with a bit more exchanges across the table.  Afterwards a bit more banter came out and she mentioned her bad choices of kitchenware. A flower, that forces extra liquids to spillover, that’s quite the highlight of the night. The corny conversation was lighthearted and fun, something I don’t really experience too often with these dates. During the last flight of wine, we looked at each other and I told her, “I would be right back as I whispered in her ear, she turned towards me and made out with me for a bit.”

I thought to myself, “Is this really happening right now? Is the alcohol, the only reason why she is really into me at the moment?” I couldn’t tell but after some back and forth, she was ready to go home. This self proclaimed ‘high tolerance lady’ was ready to hit the hay. We strolled through downtown and made out a bit more one another, she randomly blurted in a slurred speech, “You know I should hire you for a party sometime, you know quite a bit about food and drink.” I gave her this weird glance given the random response out of the blue. It was odd of her to say such a thing during our second date, as if I was some rogue bartender/chef for hire.

As we got into the car, we were trying to iron out plans for a second date. She mentioned, about all the things we could do and she’ll “get back to me” once her schedule was clear. At that point, I was too skeptical, to believe something would come out of it. I think a sober thought entered my mind, given my current run of experience that this was all a temporary fantasy. After dropping her home and going about the week, I didn’t hear from her until the day before our potential third date. She rescinded her original “3rd date proposal,” felt it was better to “stay friends and didn’t feel the chemistry.” I was confused and somewhat shocked but I politely declined and wandered into a bar later that night. As I sat there with a scotch in hand, I realized, all you gotta do is move on. So with one shot and more messages flowing, it was onto the next one…

According to my peers one would argue that I suck at life. Some would maybe say it’s “bad timing” or someone called ‘dibs’ before I even had a chance. Either way, this is all a journey for me, so let’s keep it moving.

The Single Life: Date #4, Photography and Boba

I really like this picture, I wish I can take pictures just as good as you.

This week was crazy, I literally had three dates in the same week (after work) and now this was Date #4, what a hectic schedule (hence the delay with the most recent article). If you haven’t gotten caught up on the series you can review the entire archive here.

Anyway, the back story with this particular lady, we messaged each over for at least 2-3 weeks and our schedules never really lined up until this hectic week. Worked in Silicon Valley, software engineer, bright eyed, and family oriented. You’d think she has everything I want in a person, well that wasn’t really the case. One thing I’ve realized about myself is although I appreciate intellect in a woman (and believe me being a software engineer is nothing to scoff at). There are other items that are important to me, like drive, culture, and other similar values.

This is probably the first time, that I didn’t really care what would’ve been the outcome on this date. Whether we would end up as friends or lovers, I was completely fine with that. I guess when you meet genuine people who don’t have enough of that “spark” drives up your interest, you feel at peace. This peace almost broke the opportunity when she texted a few lines and took to offense:


Her: I would be such an Asshole if I said that…
Me: Well if you did, then I would say, peace out cunt. Exit stage right :p.
Her: Wow, I can’t believe you said that…
Me: Hey now, I was just kidding as well. You said it earlier.


Granted the messages afterwards were days after and lots of miscommunication could’ve occurred. People’s real personas through online dating don’t really transpire until you meet them in person. For the first time ever, I really just didn’t give a shit anymore about my personal filter. Majority of my life, I felt the need to hold my tongue because lord forbid,  “Someone would get offended.” However as you grow older, you truly do have less “fucks” to give about life because its too unpredictable and can end in an instant. The day of, we finally met granted we still had an awkward air given our text exchange.

Boba date

However we had a nice time and took a few photos along the coastline (including the portrait I took of her) and then grabbed Boba shortly after. We shared everything from short-term goals and new travel destinations. The only problem was for the first time in a while, I wasn’t really feeling it. I knew she was because of her body language but I kept wondering to myself, “What’s wrong with me? Why can’t I like a nice girl like her?”

Was it because I was a bit shallow and she didn’t look as good in person, as she did in the photos? Or, was this “Chemistry” thing really happening right now? Either way, I ended the date within an hour and dropped her off. As I drove home, I realized maybe you’re not meant for everyone because this chemistry is crucial and that “spark” (or “tinder”)  is necessary to build that momentum. I came to the conclusion, that I didn’t mind ending as friends or seeing her for a second date but I unconsciously made up my mind. She texted me a few days later saying , “She’s taking a break from dating.” I guess not hearing from me frustrated her, I don’t blame her as I’m about to realize, the same thing was going to happen to me…