42 Dating Disasters

Love triangles. Mine was obtuse.

One night, out with the twenty-something crew, I made my way into a bachelorette party. Think Wedding Crashers, only sexier. The ladies of the bachelorette party were definitely out for a good time (most are), and they welcomed me into their midst. When I mentioned my friends, they said, “Bring them over!”

Suddenly, in the middle of having a fun night, a friend of theirs arrives late. Let’s call her “Penelope”. Despite the fun I was having, I was instantly attracted. In my latest post, I mentioned my “brain-dar”, and it was on “high” this night, despite the copious shots we had all been consuming all night. My instincts were completely right, as I found out when she challenged me to a thinking contest of sorts after a shot of tequila. Considering she had a six-shot edge (having just arrived to the party), I wasn’t surprised that I just missed the mark. Somehow, this turned me on even more. We danced together very closely for the rest of the night. I could probably identify her panties in a line-up.

Girls will talk at a bachelorette party, and part of what I picked up on was that Penelope had a boyfriend. One of my mental gifts is that, no matter how drunk I am, I will always pick up on a key detail like this. I put it in my back pocket for later. As it turns out, this was exactly the right thing to do. One faculty that does fade as I drink, however, is judgment. I made a nearly-fatal miscalculation and said something that really offended Penelope. She stormed off, probably never to be seen again. After taking a powder, chatting with some of the young men in the bathroom about the importance of condom use and with the attendant about which cologne he needed to get, I went outside to find my friends. Who should walk up to me but Penelope? She was explaining that she wasn’t really that angry and that she didn’t mean to make me feel bad. “I know you have a boyfriend. I know what’s going on.” was all I said. She immediately looked around to find out which of her friends ratted her out. Then, she admitted that she was trying to find an excuse not to talk with me anymore, so she blew the whole situation out of proportion.

Gentleman that I am, I explained that I understood her situation and offered her my number. She entered it into her phone, and after a moment or two of hesitation…. pressed “Send”. I could tell she was uncomfortable doing it, but she definitely wanted to make sure I had her number. Later that night, I checked up on her and her friend. Early the next morning, she contacted me, and we set up a date.

Unfortunately, no amount of persuading on my part was able to get the date to happen. She went back and forth for an entire week, finally canceling our plans on the day. Her main concern actually seemed to be what might happen if we ever met (and what she might say to her boyfriend). Because of this, I have a feeling that I may not have heard the last of Penelope.