What I Learned From Bad Dates

One single woman shares the relationship lessons she learned via some truly awful nights out. Come listen in.

By Caroline Kepnes

y first date was with a boy named Brian who took me to see Nuns on the Run. It was a double date, of course, and it went off without a hitch. As the credits rolled, I knew one thing for sure: I was good at dating. Oh, to be 13, naïve and wearing Esprit. Alas, kids grow up. Every date can’t be dreamy—in fact, some are plain old nightmares that make you want to become a nun on the run. But there are upsides. These dates were torture at the time, but ultimately taught me some priceless lessons.

The guy: Captain Charmsicles
The bad date: This was the most aggressively romantic night of my life. Captain
Even if he’s super-nice, if he’s not for you, don’t try to force it.
Charmsicles went all out—candlelight on the roof of a landmark building and a private, luxurious meal under the stars. He opened door after door. And I cringed time after time, then berated myself for being annoyed by the same behavior I’d always said I wanted. Ever the gentleman, he kept going for the grand kiss, thereby sending me on an obstacle course, with his tongue being the primary obstacle.

That’s when I realized… If he’s not for you, you’re wasting your time. It doesn’t matter if he’s the greatest, most chivalrous man on earth: You deserve some sizzle. And skip the guilt trip. You’re allowed to hold out for a nice guy who you actually like.

The guy: 2 Cool 4 School
The bad date: Wow, here I was at a fashion designer’s after-party for models. And this amazingly hot hipster with the right jeans and the right BlackBerry was asking me, a non-model, to go out. A week later, we met up at an impossibly hip restaurant. 2C4S seemed disappointed by the lack of product in my hair. After we placed our order, he “remembered” that he’d forgotten his wallet. Yay for me! He got up every 30 seconds to make a phone call, and eventually, just never came back. Gulp.

That’s when I realized… If you aren’t yourself when you’re talking to him, you’re never going to truly connect. I met him at a bar I didn’t like, at a scene that wasn’t my scene. If you feel like an alien in his homeland, you’re probably not going to be compatible in the long run.

The guy: Perfect In Profile
The bad date: Oh, was I smug: In my first foray into online dating, I landed a lawyer/book-lover with whom I could communicate for hours about
Witty online repartee doesn’t necessarily mean you two are destined to marry.
writing, movies, family, everything. And then he showed up for our first date. Oops. He didn’t look that much like his photo (or what I’d extrapolated from his photo), but I wasn’t going to judge, not yet anyway. We hugged hello: zero chemistry. We had the most awkward burrito dinner in the history of dating. I told him I didn’t think this was going to work; he said his hair had only recently started to fall out. Hint: It wasn’t the hair.

That’s when I realized… You can’t gauge chemistry over the computer. Can you meet someone great? Absolutely! But witty repartee over instant messaging doesn’t necessarily translate into live-action dating—and the longer you spend fantasizing about the guy in your inbox before meeting him, the more disappointed you’ll be if he’s not who you’d imagined he was.

The guy: The Renaissance (Gun) Man
The bad date: Dating a buff, classical guitarist makes you feel like you’ve walked into a romance novel. On our first date, my Renaissance man forbade me from ordering steak medium and said I would “learn to like it” rare. I bit my tongue—maybe this was finally the chivalrous, take-charge kind of guy I’d always heard existed. So I thought about his rock-hard abs and gave him another shot. This time, he boasted about shooting at his neighbor’s dog after it wandered onto his property. Needless to say, I stopped biting my tongue.

That’s when I realized… My gut doesn’t lie. I should have known this guy was bad news when he didn’t believe that as an adult, I know how I like my red meat. Dating is like driving. If you slow down when you see the yellow light, you won’t have to slam on the brakes when it turns red.

The guy: The One Who Was Meant to Get Away
The bad date: This friend and I had been flirting for years, but at least one of us was always unavailable. Then one magical night, he called with a new urgency in his voice and asked me to dinner. We sat across from each other like Lady and the Tramp. He said he wanted to ask me something. I smiled. I could practically hear Etta James singing “At Last.” Then he asked me to put my hair in pigtails and do something generally solicited in red-light districts. I blanched, he asked for the check, and before it even was, it was over.

That’s when I realized… Movies make us believe that the one who got away really is The One. But in real life, if you keep someone at a distance for a long time, there’s probably a reason. Now I know that if I analyze a guy more than I talk to him, something’s not right.

Caroline Kepnes has penned two episodes of The CW network's drama 7th Heaven and writes a daily column for E!Online called Reel Girl. She has contributed to Entertainment Weekly, TV Guide and Los Angeles Confidential.

For the guy’s perspective on bad dates, read The upside of awful dates.

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