42 Dating Disasters

Cougars... they know what they want

A buddy and I were out having a few drinks at a local bar. It’s normally a pretty good scene, full of HAPS or better possibilities. But even when the woman count is low, there are other things to keep us occupied. For whatever reason, the place we were gets pretty dead early on, especially mid-week, like this time. Like so many good stories, this one starts “I’m sitting there, minding my own business….” My friend and I were having our last drinks before we moved on, and that’s when she pounced. I like women to take the initiative sometimes; but if you’re a cougar and taking the initiative, you’d better look like Courtney Cox.

I could tell right away I was in for it, but I didn’t want to be rude. I had never seen this woman before, so I didn’t know who she knew (a lot of people “know the owner” at this place; but I think a lot of people say that, too). It seemed like a good idea to try to be polite and just try not to get mauled. No such luck. She must have started drinking some time around noon, because she was totally shit-faced drunk. That might have explained why she started pawing me right away. Hands all over my face and hair. C’mon, lady. I did NOT invite you to touch me in any way. When I smile and nod and then turn away from you, with my only view the overweight, hairy bartender… that should be a clue. Then, in what had to be one of the worst moves I’ve ever seen, she pinched my cheeks. In addition to being a huge invasion of my personal space it had exactly the wrong effect. I told her, “Wow. You just reminded me of my grandmother.” For some reason, this didn’t have the desired effect, either. Instead, she told me about her daughter who she came with to the bar (she was 30, according to Mom). Then she went on to explain, proudly, that she was her youngest daughter. Youngest. Meaning there were older daughters. More than one. Okay, so assume there were only 2 years between each, and there were only 3 daughters. That means she has to be at least 50 (and that’s being generous; 16 + 2 + 2 + 30). I mean, I’m flattered and all, but I don’t think so. To top it all off, she then starts telling me about her dead husband. And you know, I felt bad for her, but is this how you pick up men? Does this ever work? Actually, the best part is that my buddy backed off completely, hiding behind a tree somewhere instead of bailing me out! To be honest, it had to be pretty funny to watch, so I might have done the same thing.

The same rules apply to darts, pool, and picking someone up at a bar. A few drinks might help your game, but things can get out of control if you have too much. In any case, you still need some kind of talent and a game plan to expect success.

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.

One man, one vote

I’ve had a pretty active fantasy life, especially when my real life didn’t live up to my expectations. Whenever I travel alone, for example, I think about getting propositioned. What guy doesn’t want to be so powerfully attractive that a woman throws herself at him? And what guy wouldn’t want to walk out of a bar with a lay at the end of the night?

This guy. At least on this night.

Since I became separated, I’ve been hanging with a younger crowd when I go out. It’s been a lot of fun so far, and they are able to introduce me to people who are younger and have a very different perspective on life. After so many years as a “family man”, it’s good for me to shake things up a little bit. One night, a small group of us went to the local dive bar, where we ran into some folks that we knew from being there before. One of the people there was a woman who I absolutely knew was interested in me. After a previous night at the bar, she sent me a message letting me know that I was the hottest guy in the bar. Considering this is a dive bar, I wasn’t quite sure how to take that. Also, she sent this message to me after making out for 15 minutes with one of my friends. I was pretty sure how to take that. Slut.

Now, we’re going to the bar on this night, and the slut sits down next to me and starts complaining about how this other guy in the bar slept with her, then never called her. “Slut” status confirmed. I was unsure where she was going with this. What angle could she possibly be playing? Was she actually interested in me? And if so, why on earth would she bring that guy up? There wasn’t much going on, so I went outside to talk with a friend. After about an hour on the phone (and the corresponding hour of sobering up), I went back into the bar. I don’t know if you’ve ever noticed, but alcohol really goes straight for the bladder. In my case, if I didn’t get to the bathroom soon, it was going to be New Orleans all over again.

Now I’m heading straight for the men’s room, and this woman grabs my arm, pulls me in close and just straight up offers to go home with me… or just to my car, if I prefer. In situations like this — ones that I never in a million years thought would happen to me — I freeze up. So, I just resumed my original plan, excused myself, and rushed to the men’s room door. Which was locked. Escape was so close, but now I was trapped in a tiny dive bar only a few feet away from someone I was desperate to get away from, only inches from a room I was desperate to get into. I felt my stomach sink.

Fortunately, my friend lived around the corner from the bar. I told him I had a potty emergency (and that there was absolutely no way I was even getting close to touching the bar skank who just propositioned me). He gracefully rushed me out the side door. Of course, “you know who” was waiting when we came down the alley. I decided that was a good time to appear more drunk and disorderly than I actually was, and we made a break for it. All ended well enough, with me happier than I’ve been for a while to be in my bed alone!

Not as cool as it looks

I met “Betty” on Plenty of Fish, a popular, completely free dating site. I think they make their money selling insecure men and women dating advice in the form of books, DVDs, and live seminars. At any rate, I tried to start a conversation with Betty, but she just… wouldn’t… go. I would ask questions about her interests and get one-line responses back. Often, only one of my questions would be answered at all. Some people don’t communicate well in written form, but I just couldn’t even bring myself to ask for her number to find out.