The Worst Date Experiences Of My Life, An Accounting

Sitting down and figuring these out really made me see how many of my "bad" experiences actually had far more to do with my behavior than anyone else's.
Publish date:
September 12, 2013
Dating, bad dates

Sitting down and figuring these out really made me see how many of my "bad" experiences actually had far more to do with my behavior than anyone else's. Those dates didn't make the list. What we are left with is the real gems, the ones that stung, that stayed with me, and that turned me into the crotchety old grump I am now.

But in all seriousness, I am so glad that we live and learn. That comforting knowledge allows me to take all the "bad" dates and turn them into experiences that make me a better dater, and potentially a better girlfriend, in the future.

10. The Houdini:

To the best of my memory, this has happened five times in the last 2.5-3 years. Who knows what I've suppressed. These dates are actually amazing. There's nothing "worst" about them. They are hours spent having an absolute blast with men whose company I enjoy. Why are they on this list? For what happens after. Which is nothing.

No calls, no texts. No second dates. It's as if they've evaporated into thin air or been beamed up to their home planet. Bon voyage, shitbird.

9. The Harsh Critic:

After a recent online date and I spent two lovely dates together (to be fair, I didn't feel, like, the Earth move or anything, but I had a nice time and he seemed like good company), I asked him out on our third date. His response? "I'm gonna pass."

No, "no, thank you" or "I'm sorry but I should decline," no, no. This guy will pass. On me.

Why did I feel the need to ask him on a 3rd date and bring these biting words upon myself? When we said goodbye on our 2nd date, he kissed me. For a while. In the middle of the street. In public. Mixed signals? Naaaaah, those don't exist, right?

8. The Visitor:

Waited two hours to tell me he doesn't actually live in New York. I don't have anything else to say about this person.

7. The Amazon Review:

A friend fixed me up with her boyfriend's co-worker. So sweet of her. We met, he seemed nice, but really wasn't for me. As he walked away, literally as he was walking, he texted me "Did I live up to your expectations?"

Sorry, pal, I usually wait an hour or so before reviewing a product. Good grief. I don't like being put on the spot. Not about my coupled-up friends hoping to live vicariously with the details of my dates, or by the date himself, needing an affirmation that girls like him.

6. The Dick:

And this is some high school shit. A guy I went out with twice (aggressively) tried to sleep with me on the second date. When I refused, he left. He later told me was actually gay. But like, in a very matter of fact way. "Wait, you didn't know I'm gay?" Meanwhile, he told our mutual friends he told me he was gay so that I'd leave him alone. Because I wouldn't stop hounding him. That fear of rejection can really get to a guy, huh?

5. The Favor:

I met a guy I was really into during a time when I hadn't met anyone I was into in a good long while. I met this guy, asked him out, and he dragged his feet for weeks. But I didn't let it go. I wanted to at least find out if there was something there. There was. We had a great time together.

Such a great time that after four drinks or so he let me know that he really never wanted to go out with me. Thanks for throwing me a bone, I guess? We dated for a month or so, after which he invited me to a party at his house with all of his friends so that I could meet them. Then proceeded to ignore me 90% of the night and yell at me for the other 10%. I suppose I should have trusted his instincts.

4. The Team Player:

This one actually made it into the New York Times, launching my foray into the world of dating documentation. If I could I'd dip this non-date in gold. A guy I found online made plans to get drinks with me after we both wrapped up dinner with our respective friends. After dinner, he texts, setting plans to get a drink.

His second text: I'm here with five of my college friends who are in town, cool? No it is NOT COOL. I've never met you before! Now I have to meet five of you? Netflix and glass of wine sounds like more fun than that project, thanks.

3. The Embellisher:

Notice I do not call him "The Shorty." Because your height doesn't matter dude, until you lie about it. This has happened six times in the last 14 months or so. Six times. I don't mind dating someone short, I mind dating someone who lies. Learn the difference.

These next two really take the cake, hence their spots in the places of honor.

2. The Coffee Date:

This gentleman found me via a blog post I did and asked me out in what was hands down the most gentlemanly email I have ever received. I was so flattered. I didn't know what he looked like, and didn't care. I met him for coffee. Once he walked in, it was clear someone else had penned the letter.

He stared into his coffee cup for the 35 minutes I managed to stay on the date. If I wanted conversation, I had to pry it, with force, from his mouth. I don't know if it was nerves, or if he was just disappointed in me, but this was the most awkward 35 minutes of my entire life. I left comforted actually, this being the first truly bad date I'd ever had, I felt confident I could handle anything. I was wrong.

1. The Diner:

Let's ignore for a moment that he looked nothing like his photos. To this day I am confident they were photos of an attractive relative. But looks don't matter that much. (Lies do, but whatever.) We sit down, chat about the extensive beer selection, I attempt small talk. Again, I'm driving the conversation, asking all the questions, or sitting in silence. Don't believe me? OK.

He read the menu for so long I had time to text my girlfriend a paragraph containing three sentences. When the server arrived, I ordered a beer. He ordered scallops. SCALLOPS. Who does that? Who orders a full meal when their (first) date orders a drink?

I was planning to skid-addle after my beer but now you've locked me in for your leisurely meal! Where you don't ask me anything! Or talk much! Because you're eating! I checked work emails, texted friends, and sat in so much silence I didn't date again for three months. Some wounds cut deep.

All right Universe, what else you got? I'm here. I can take it.