6 Mistakes That Kill Your First Date

And also, what to do instead.

One of my worst dates showed up in a baseball hat and denim shorts. He corrected me three times, insisted I was an amateur writer, and then left early to have dinner with his mom.

No, wait…

My worst date tried to finger me on his mom’s couch while she was putting away the dishes.

“My mom’s cool with it,” he said.

Actually, my worst date was probably the one where he brought a guitar. Don’t ever bring a guitar to a date. Of course, I’m forgetting the date where someone tried to convince me to howl at the moon with him. Maybe I’m being a little judgmental here.

You know, all of those dates sound pretty bad.

Surely you can do better.

Let’s flip things around for a minute. It’s not always the guy. I’ve also been the problem on a lot of first dates.

I’ve tried too hard to sound smart.

I’ve tried too hard to come off as funny and adventurous.

I’ve tried to be what I thought the other person wanted, and that always ended in disaster.

The worst time I screwed up a date — I bought an obscure painting for way too much money and hung it up on my wall. He was working on an M.A. in art history. When he arrived, I showed him.

I wanted to impress him.

He tried to admire the painting for a few seconds. Then he asked, “So it looks early 20th century. Who is this?”

I stuttered for a few seconds. Then he laughed. “You bought a painting, and you don’t even know who the artist is?” My face went red, but he didn’t notice. I’m so pale, disgrace looks like a mild blush.

Guys try to impress girls for sex. Girls try to impress guys to keep them around. In the end, he didn’t hang around. It’s a little humbling to know that you’re someone else’s worst date story.

The first date always causes the most stress. It feels like an audition, or a job interview. You don’t know how to act. And that advice, “Just be yourself” doesn’t help — at all.

You probably know the basics, but let’s cover them anyway:

  • Dress like an adult
  • Show up on time
  • Don’t brag about yourself
  • Don’t get too personal off the bat
  • Ask her questions (Are you from here? Where do you work? Do you have brothers and sisters? What music do you like? Do you read?)
  • Answer those same questions about yourself

You can always get creative and do something bold, something unexpected. If she’s a food critic, then do something bold and take her on a picnic with sandwiches and bicycle riding.

Give your date the PG version of you

This solves the no-win situation of just being yourself. No, you can’t try to be somebody else. But you also can’t show up with all your baggage, religious views, and unfiltered political opinions.

Of course, if the wall is super important to you — then you might as well skip right to that part…

Sure, they’re evaluating you. And vice versa. But what you’re really doing is evaluating your fit — that’s all.

You’re seeing if you like spending time together.

With that, here’s 6 things you should try to avoid if you want your date to go well. Honestly, a date goes badly for one of these reasons. Stay clear of them, and you’ll at least make it to a second or third.

1. Expecting sex right away

You wouldn’t think a lot of guys or girls walk into a date expecting sex or heavy petting. But they do.

That’s mistake #1.

Sure, sometimes it happens — when you least expect. That’s the important part. You didn’t expect it.

Conversation leads to some flirting, some hand-holding, and before you know it your arm’s around her waist.

But usually, it doesn’t work that way.

This is the kind of behavior that leads to casual sex. There’s nothing wrong with that, but someone who’s up for casual sex isn’t someone looking for a long term relationship.

So just take sex, kissing, and all that stuff off the table for the first date. You’re focusing on conversation and fun. Forget about sex, and I promise you’ll have a much better time.

2. Judging her tastes and interests

She likes Katy Perry and Taylor Swift. You’re more of an Alice In Chains kinda guy. So what? Deal with it.

You’re going to miss out on a lot of love if you reject every girl who likes Beyonce or Rihanna or, god forbid, Adele.

You don’t have to like all the same music, shows, celebrities, or movies. And if you spend half your date trying to convince her that there’s a real artistry behind The Fast and Furious franchise, you’re going to kill it — and there’s nothing Jason Statham can do.

3. Trying too hard to sound funny

Now is not the time to practice your standup routine. Real humor is spontaneous. If a joke occurs to you, then say it. Otherwise, don’t try to make her laugh. That’s a suicide run.

Besides, making her laugh isn’t all that important on a first date.

You’re way more likely to say something you think is funny, something you assume she’ll find funny. This is where you might instead say something offensive, or just plain lame.

This one also applies to other things, like trying to sound too smart, too successful, or too… anything else.

4. Telling her your college drinking stories

Honestly, she doesn’t care how wild you used to be. She doesn’t care how many shots you could do in one night.

She doesn’t care about all the times you hooked up with a friend, woke up in the wrong dorm room, or broke something.

She doesn’t care how many times you almost got arrested, but charmed your way out of it because you were white and harmless — at least according to a sober cop with training, and plenty of weapons.

5. Talking a lot about ex-girlfriends (or wives)

At least save this for the third or fourth date. Talking about past relationships doesn’t impress anyone. We’ve all dated a good bit.

We’ve all had our hearts broken once or twice.

If you haven’t, then still… keep all that to yourself for now. The more you say about your exes, the more you’re revealing about yourself. You’re presenting the notion that you’re still hung up on them.

It’s a bad look on anyone.

6. Giving her too many compliments

A compliment is a straightforward way of trying to earn someone’s approval, trust, or respect.

It’s a nice icebreaker.

But after the third compliment, it starts to feel a little awkward. It looks like you’re falling back on a playbook. Instead, try to keep things somewhat casual. Stop reaching for compliments, and just show interest in her. That by itself is a huge winner.

Try to relax and have a good time

Just let go of your expectations, and stop trying so hard. It’s just a first date. A first date is really just about establishing rapport.

And maybe watching for any red flags.

But mainly, you’re trying to have a good time. Hey, sometimes a date might go bad for reasons that have nothing to do with you. Your date might show up in a terrible mood, or maybe she’s making one of the mistakes described above. Just enjoy your beer/wine/coffee and go home.

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