5 Good Things About My Worst Date Ever

5 Good Things About My Worst Date Ever Image
I’ve never been a big dater; I’ve had boyfriends (and two girlfriends), but most of them I met through friends or at parties, and our romantic relationships grew out of being friends first. Actual first dates, complete with jittery nerves, fashion angst and awkward conversation aren’t my forte. The whole trying-to-get-to-know-someone-in-an-hour thing makes nervous, and seems way too much like a job interview that something conducive to finding someone I could fall in love with. But since I’m 34, single and looking to be in a relationship, I figured I should finally give online dating a try, so I signed up for OkCupid and HowAboutWe.

The results have been mixed, but I want to share five things I learned about a Very Bad Date that might help you in the dating jungle. I had proposed the date – a free comedy show at the Knitting Factory in Brooklyn – on HowAboutWe. The premise of the site is that you either respond to cool-sounding dates, or propose your own. This was a show I’d been wanting to check out for over a year, so I figured I’d rather do so with company. It took us about a month before we were both free. I knew very little about the guy, but was excited about the prospect of meeting someone new.

Well, my expectations were on the high side – the very high side, as it turns out – but I’m still glad I went on the date. Here are five reasons why:

1. Getting Dressed Up is Fun No Matter What

That day, I put on a flower-pattern Yumi Kim dress, got a manicure and pedicure and – something that’s a challenge for me – managed to fit all my stuff into my shiny new red purse, so as to make a good impression, rather than lugging my usual three to four giant bags. My date didn’t say a word about what I was wearing; now, he doesn’t have to, and maybe he wasn’t impressed, but a small compliment goes a long way. But wearing the outfit and matching bag, taking the time to make sure I looked my best, made me feel good even if he didn’t appreciate it.

2. I Realized I Have Good Social Skills

I’d arrived uncharacteristically on time, and proceeded to look around and order a seltzer, then get a table. He came in about five minutes later, which was fine … until he told me he’d seen me come in. What? That struck me as creepy; he’d known I was in there and deliberately waited five minutes before joining me. I’m often late, but I would never do that to someone.

He’d recently been on a trip abroad, so I tried to draw him out about the trip, with little luck; for the most part, I got one-word answers. I was frantically trying to come up with things to talk about, but instead got really odd answers (such as “I live in the Bronx and Brooklyn”) that I couldn’t figure out how to follow up on. I was starting to feel a little crazy, until I realized that I’d tried my best, and that sometimes it’s better to just be silent and wait it out. I may not be the perfect conversation partner, and sometimes ask too intense questions on a first date, but at least I didn’t revert into silent mode.

I’d finished my seltzer and was sucking on the ice, a clear sign that it was time for him to at least offer to get me a drink. I’m not a dinner whore by any means but that would’ve been the polite thing to do. Instead, I got up to get my own drink, and offered to get him one. He declined, but when I returned and said the bartender had comped my seltzer, he replied (perhaps his most egregious dating faux pas), “If I’d known it was free, I’d have asked you to get me one.”

The situation was so ridiculous I couldn’t help but be amused and again, give myself a pat on the back for having the graciousness to offer him a drink.

3. I Got to See a Fun Comedy Show

The comedy show wasn’t the best I’d ever seen (one guy talked about how he fantasized about chopping his exes’ heads off and making a mobile over his head!) but there were enough funny moments, including a guest appearance by 30 Rock’s Judah Friedlander, that I laughed more than a few times. I was very glad we were not on a dinner date where the lack of chemistry would’ve seemed interminable.

4. I Flirted With A Cute Guy (Not My Date)

Now, this may be a cardinal sin of dating – thou shall not flirt with other people while on a date. But first let me say that I didn’t start it. When I finally broke the deafening silence at my table to get myself another seltzer, I ran into a guy I’d had a few dates with last year. He complimented me on my outfit, which made me smile, and sort of made up for my date not doing so. I was tempted to simply ditch my date and hang out with him, but I didn’t, though I did drop him a line when I got home, sharing the highlights of my date, and we’ve been emailing ever since.

5. Instead of Feeling Sorry for Myself, I Got “Out There”

I think I had this fantasy that the minute I conceded to the world of online dating, the perfect person would be waiting at the click of a button. Clearly, not so much. Still, if I hadn’t met him in person, I’d never have know that, and just by being out, rather than slumped in front of my TV or laptop, I felt more confident. And I might’ve even parlayed it into a date – with someone who’ll actually talk to me.

Tell us: Would you rather go on a bad date than not date at all? Share your Good Bad Date stories!

Suggested free e-books to read:

Helen Ferry - Get The Facts About Condoms
David Deangelo - Double Your Dating Sex Secrets
Joseph Matthews - The Boyfriend Is Not An Obstacle

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