Your Survival Guide to Your First Date After Divorce

Dear Adam: The trauma and stress of my divorce are behind me, and I’m finally ready to get back out there. But now I’m petrified at the prospect of having my first date after divorce. Help!

I hear this so often from women who were married for years — even decades. It’s scary to make yourself vulnerable after what you’ve been through, but I’m here to guide you through this first big experience, and I promise it will get easier after.

Before You Go on Your First Date After Divorce…

Let me start with one piece of advice before I give tips on what to do on your first date after divorce: don’t go on a date until you’re ready. I know you may try to rush through the grieving process so that you can get back to feeling normal (whatever that looks like for you now). But please understand that you have been through a hugely impactful experience, whether you initiated the divorce or not. You may think you’re ready to date again when in reality you need a bit more time to figure out who you are now and what you want.

Give yourself that time. Dating can wait. It will always be here, waiting. And don’t start dating after a divorce with a vindictive heart (“If he sees a post on Facebook of me and man, he’ll go crazy!”). Go on a date when you’re truly ready to open your heart to love again…or have a good time!

1. Don’t Overthink It (You Don’t Have to Marry the Guy)

If you’re recently divorced, think about this question: when was your last first date? It was with your ex-husband, right? So it might have been 5, 10, 30 years ago. You’ve all but forgotten the nervous butterflies that settle in your stomach as you put on your makeup in preparation to meet a near stranger. Understandably you might be stuck in your head right now.

“What if I don’t like him at all and he’s into me?”

“What if I’m into him and he doesn’t like me?”

“Should I order a big meal or a salad?”

“I wonder if he’d ever remarry.”

I know it will be insanely difficult to follow this advice, but: don’t overthink it. The more energy you put into the whatifs before the date, the more energy you waste. There is no way to know whether you’ll go on one date with this man or a thousand dates. The former is more likely at this point in your life, and that’s okay. You’re not looking for Husband #2 right now. You’re simply looking to get back in the dating pool and get to know new people. You have nothing to lose except a few hours of your life.

2. Set Out to Just Have a Good Time

If you set your expectations low, you can’t be disappointed. I’m not suggesting you assume the date is going to go terribly, but rather than thinking that this might be Mr. Right (already), think that you’re getting taken out by a man who has so far seemed to be generous with the compliments. You might learn something from him. Have a few laughs. Have a great experience.

It might not be a love match. But you might end up with a new tennis partner or someone to expand your social circle.

Take a minute to ask yourself: “what are my expectations about this date?”

Your answer could be something like:

To finally try that new Ethiopian restaurant.

To get practice talking to a man now that I’m newly single.

To practice flirting.

To laugh.

These are tiny, achievable goals! You have absolutely no control over how this date will go or the outcome, so center yourself by having one or more tiny goals like this, and you’ll be fine.

3. Agree to Meet Somewhere You’re Comfortable

You’re nervous enough. Don’t add stressors like going somewhere new with no easy parking to make it worse. Suggest a coffee shop or restaurant in an area you’re familiar with. That way you won’t be distracted by your surroundings and can focus on talking to this man.

You might think you should meet at a nearby place in your neighborhood, but I’d think twice about that. For one, if you know people in the area, then you might have to deal with busybodies on a first date. And if he knows you live nearby, he might want to walk you home. It’s too soon for him to know where you live (more on that in #7).

If you’re meeting in an area you aren’t familiar with, consider driving by beforehand so you get the lay of the land and can figure out where to park.

4. Make it a Short-and-Sweet Coffee Date

I’m a big fan of the one-hour coffee date, especially for a first date after divorce. You have a timeframe to work in your favor if the date isn’t going well and can make an excuse to leave after an hour. It doesn’t take that long to drink a cup of coffee!

Also, it’s affordable. Since this is a first date and you have no idea whether you’ll have chemistry with this guy, do you really want him to shell out enough dough to pay for a fancy dinner? He probably doesn’t. For under $10, the two of you can test the waters and see if you want to plan a second date.

There’s less pressure for you if it’s a short coffee date, particularly if you’re overwhelmed with nerves. It’s just an hour of your life. You’ve got this.

If the date goes well, you can always expand it by walking to a nearby park or hitting early happy hour for a glass of wine and appetizers. Those dates that stretch on for hours are the best!

5. Don’t Drink Too Much

If you meet for drinks or dinner with drinks, it can certainly help to have a glass of your favorite adult beverage to quell your jitters. But realize that having two or more could seriously impair your judgment. You might not have been all that attracted to this guy at first, but as you get tipsier, he’s starting to look a whole lot better (that’s what beer goggles are all about! Which, by the way, scientific research has proven is a real thing.).

Drinking too much might put you in a compromising situation or cause you to make bad decisions, like sleeping with the guy. Hey, if you knew before the date that you wanted to sleep with him on your first date, more power to you. I just don’t want you to make that decision while you’re impaired.

Interestingly, what you order to drink can affect how attractive your date finds you. In a survey conducted by British dating app Trueview, it was found that 27% of respondents thought that the most unattractive drink someone could order was a shot. That was followed by a pint of cider as a less attractive beverage to order (probably more prevalent in the UK than here).

So what should you order? White wine, cocktails, red wine, and rosé were all acceptable in the survey. Interestingly, 14% of respondents said they would judge a partner based on what they ordered, so be aware of what your drink order might say to your date.

Also, I know you might think this is silly, but don’t leave your drink alone with your date. Remember that you don’t yet know this man, so you can’t trust him. Finish your drink before going to the ladies’ room, then wait until you’re at the table to order another one.

6. Get to Know Him Via Text/Phone Beforehand

via GIPHY

The more time you spend getting to know this man before your first post-divorce date, the better you will be set up for success. Some guys on dating apps want to meet as soon as possible rather than getting to know you via text, but make your own rules. If you’re not comfortable meeting so soon, you don’t have to. Tell him that you do want to meet him, but that you’d like to spend a few more days texting or even have a phone call or two.

Or…you can just tell him you’re busy until later in the week (might even be true) so that you have more time to talk before the date.

The reason for this is that you might realize that in no way are you compatible with this man during the course of your conversation, which would save you from having a bad first date after divorce! Also, you’re establishing that you have certain requirements. If he’s too impatient and refuses to wait to meet you, he’s not the right guy for you.

7. Meet Him There Rather Than Letting Him Pick You Up

The last time you dated, you pretty much chose from your circle of friends in college. You didn’t have to worry about being roofied or crazy men who might chop you in a million pieces. You’re older now and less willing to take risks with your life, so practice a few safety tips when your dating after a divorce.

One is to drive yourself there. That way you aren’t relying on him to get you home, particularly if the date didn’t go well. Also, he doesn’t need to know where you live until you know you can trust him. What happens if the relationship ends badly in a few weeks or he just feels rejected because you weren’t into him after the first date? Online dating horror stories are a rarity, but they do happen. Protect yourself.

And if he insists over and over on picking you up, saying he wants to be chivalrous, explain to him that if he has a sister or female friend, he’d want her to be safe, right? So make a rule that no man will pick you up for a first date ever.

8. Let a Friend Know Where You’re Going

Here’s another safety tip: always tell one or more friends when and where you’re going on your first “after divorce” date (and all subsequent first dates). Having someone keeping tabs on you keeps you safe.

I know women who have downloaded apps that track where their cell phones are so that their friends could track them if something went wrong on a date. It’s extreme, maybe, but your safety should be your top priority as you meet men you don’t know yet.

9. Wear Something You’re Comfortable and Confident In

I’m sure you’re worrying about what to wear on your first date after divorce. I get it. It may have been years since you got dolled up and wanted to be attractive to a man (maybe your default look during marriage became yoga pants). You’re looking at what you think are sexy dresses in the store, wondering what it takes to be appealing to a man at this phase of your life.

Let me let you in on a little secret: men don’t need you in tight or low-cut clothing. The guy you’re about to go out on your first date already finds you attractive. You’ll look great to him in something you feel confident in. And it should be comfortable! If you’re fidgeting all night with a shirt that is cutting off your circulation, it will distract you from having a good time.

Pick a color that you know looks great on you. Wear something you’ve worn before, that you know is comfy. Leave that skintight dress on the rack.

10. Keep Your Expectations Low

In the days before your “first date after divorce”, you start fantasizing about what falling in love again will be like. Or having sex with someone new after being with the same man for so long. These things will absolutely happen to you…but not necessarily with this man, the first man you’re going out with after being married.

Seeing a photo of a guy on a dating app and texting back and forth presents a sort of false expectation. You might hit it off via text, but meet in person and have zero chemistry. You might find out he’s rude to the waiter, and that turns you off. He might push to go back to your place and you’re definitely not ready for that.

So keep your expectations low. Absolutely nothing has to come out of this date. You can’t know ahead of time whether this guy is right for you or not. Spending time together in person is the only way you’ll know whether you even want to go out with him again. So don’t start daydreaming about your new boyfriend until you’ve actually met him!

11. To Kiss or Not: It’s Up to You

Everyone’s got an opinion about whether or not you should kiss on a first date. Some say that kissing on a first date gives the man the wrong idea about how fast you’re willing to move (unless you are willing to move fast…then it’s accurate, I guess). Not kissing on a first date might indicate that you’re not interested when you are.

Toss all the advice you find online out the window and decide for yourself whether you’re comfortable smooching this guy after spending an hour or two together. You never know; the chemistry might be so insane that you’re drawn together like magnets.

And that’s okay.

Or you may like him but be cautious because you want to roll slowly with this whole dating thing.

And that’s okay.

The guy doesn’t get to dictate whether you kiss him or not. If he leans in for a kiss that you’re not ready for, sideswipe the kiss and give him a peck on the cheek. You can even tell him you want to go slow. He should respect you for it, and if he doesn’t, ditch him.

Conclusion:

I can’t really keep you from being nervous about your first date after divorce, but I can tell you: you will survive. You might even enjoy yourself. Just go into it with a light heart and minimum expectations, and you should have a good time.

And if the date is absolutely terrible, you can laugh about it with your friends!