A First Date Guide for the Newly Divorced

Okay, so I admit that photo is a little misleading, because having sex is actually not on my list of tips for what to do on your first date after divorce. But I got you to click on my article, so, you may as well read it. Logical? Yes. Clickbait? Yes. But you clicked.

Basically, nobody’s first date after divorce is good. It’s just one of those facts of life, like the first time you speak in public or the first time you ride a bike. In all of the above situations, you are going to be terrified, sweaty, self-conscious, and there’s a decent chance you may end up scraped and bruised or hiding under a table. It’s fine. You’re human, and now divorced. You’re a divorced human.

If you’re anything like this human, you might have been avoiding going on a date for exactly the reason I’m describing here: you know it’s going to be bad. You’re absolutely right. Maybe.

The thing is, you can’t avoid it forever.

Once you get through all the stages of grief following your divorce—and I’m not saying rush through that part, because it’s important stuff—but once you do get that part out of the way, going on a date is kind of just something you have to do. Maybe it will take you two months, maybe two decades; maybe you’ll end up in a relationship, maybe you’ll decide to stay single for the rest of your life. Everybody’s different. But you do have to face it one way or another.

When you finally get to this point, here is the crucial thing: just get all the awkward out of the way in one date. Embrace the bad dateness, because that is most likely what it will be.

What follows are the steps to success on your first date after divorce.

1. Choose someone it’s probably not going to go anywhere with. The main thing is to get rid of hopes and expectations as much as possible; pick someone you don’t have a crush on if possible. I would also advise not to pick someone you have to see on a regular basis, like a co-worker. Once you have a willing date who you feel lukewarm about, proceed to Step 2.

2. Pick a place you don’t really like. Just in case you embarrass yourself, it’s best to choose a venue for your date that isn’t crucial to your weekly routine, in case you have to avoid the place for a little while after this. Low lighting and not many people would be ideal also.

3. Order something awkward to eat. For appetizers, order olives so you have to spit out the seeds on your plate and feel gauche, and/or bruschetta, so the tomatoes fall off your bread into your lap. Go into the date planning to leave with some kind of food stain on your clothing. For your main course, order spaghetti so that you have to slurp it, and/or ribs because ribs are awesome. Enjoy yourself–you might as well.

4. Drink. A Lot. Usually drinking more than one or maybe two drinks on a date is bad form. In this case, it’s necessary to have at least two drinks, probably more. It depends on how many it takes for you to lose emotional inhibitions, because you need to be free and easy for Step 4. (Note: Please don’t drink and drive; one-night stands are also not advised. #NoJudgement, though.)

5. Tell your date how much they remind you of your ex. It’s time to get real, and by real I mean embarrassing. Talk about your ex—you know you need to. Apologize profusely, but be honest. Dating reminds you of marriage and that reminds you of your ex, and you’re going to just name the white elephant because you’re DRUNK. You’re in a weird place. It’s okay. 

6. Give your date a list of the three big ways you failed as a partner. This will feel like a sort of confession and will make you feel better, lighter even. Then shift the conversation away from yourself, because you’re getting really boring.

7. Be entertaining! It’s the least you can do, since you’re probably a huge drag to be on a date with. Memorize a few jokes and compelling questions beforehand. When your date gets that glazed-over look that means they’re deciding whether to hate you, break out the jokes and compelling questions. Order them an extra dessert and proceed to Step 8.

8. Pay the whole bill. You owe this poor person a free dinner.

9. Thank them. You needed to have this date more than your date needed to be there for it, probably. This person did you a great service, and they should be made aware of that fact by the end of the evening.

10. Resign yourself to being someone’s “worst date ever” story. Own it. That’s where you’re at right now. Embrace it.  

Now you can really start to move forward.

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