Single Life Date #3: The Political Outreach, Within Reach

So do you do all these creative shots and production times with this new gig?

As luck would have it in an earlier post I refer to a previous date of mixing one woman for the other.

Ladies and Gentleman, let me introduce to you Ms. Forager. Unlike Ms. Soylent this lady had it going on in all sorts of ways. When I first swiped on Ms. Forager, I got a bit nervous because there are moments that even we we guys feel that we’re truly, “Swinging for the fences.”

I like to believe, that I can go for anyone I want, even if this idealism would eventually lead me to nowhere. I figured, “What did I have to lose?” If Dax Shepard can get with my old crush Kristen Bell, anything is possible right? Right? As luck would have it, I soon found out the hard way that not all that glitters is gold.

She came from an upper-middle class background, was involved in politics and now is leading one of the notable startups in Silicon Valley. I thought to myself, “Damn, why does she want to meet me?” We were dead set one Thursday evening at one of the bars in San Francisco. It was somewhat cool evening and I’d already work a 11 hour shift, so my brain is already at the brink of exhaustion. When I first laid eyes on her, she looked so much better in person the picture didn’t do her justice by a long shot. As we shared drinks, we had great banter and even did some people watching.

We exchanged investment ideas and enjoyed our time to extend for dinner. She seemed pretty simple and well traveled, having come from Singapore and the Maldives. Throughout the night although we were close, we didn’t make any physical contact of the sort. No Hand Holding, playful taps on the arm or even a couple’s arm lock.  I offered to walk her home and we finally reached her apartment’s front door. I thought to myself, “It’s now or never.” I went for the hug. It was at that moment, I felt the ‘ass out’ hug of a lifetime (shot down).

Yeah, it wasn’t going to go anywhere beyond our date but she had a fun time and shut the door behind her. As I walked back to the terminal, I hated to admit that she was above my league. I was nowhere near her level of success, lifestyle, or cultural background she had been hoping for. This wasn’t the first time and this most certainly isn’t the last. The biggest lesson learned was no matter what stage at your life, sometimes you gotta live in the moment and take as many at bats as possible. You never know what’s the outcome and you might get lucky sooner or later. Now onto the next one…


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