First Date With Your Ex? Here's What To Do

Your breakup is starting to feel like a distant memory.

You’ve been talking to your ex, seeing them more and more, and it feels like you’re connecting all over again. This is your second chance at a first date.

So what can you do to avoid screwing it up like last time?

First off, congratulations.

Getting to this point after a breakup is one of the toughest things you can do.

But don’t get too cocky! You still have a long way to go before your relationship is out of the woods.

Now, this date shouldn’t be the first time you see your ex after breaking up.

If they’re coming over to pick up the hoodie they left at your place and you show up with a dozen red roses, there’s going to be a problem.

If you had to beg for them to meet with you, it’s not a date, it’s a pity party.

This is for that “testing the waters” date when you’ve already reconnected and things seem to be heading in a romantic direction. But are you there yet?

How can you tell if it’s a “date”?

It can be tricky to figure out if your ex sees it as a date or not. Here are some signs to look for.

Have your previous meetings been positive?
Have you had a conversation about maybe trying again?
Have they been reaching out to you to talk about things unrelated to the split?
Have you two been flirting?

If you answered yes to these questions, that’s a good sign that they want to rekindle things with you.

Another thing to look for is the tone and content of your conversations recently.

Are they generally positive and kind towards you?
Are you both still rehashing the breakup or are you acting like it never happened?

In the end, you’ll never know for sure if it’s a date or not because your ex doesn’t either! The rekindling phase after a breakup is tricky territory.

At some point you have to take a leap of faith and just go for it.

Your ex is conflicted so the best thing you can do is provide a sense of certainty. This means act as if it’s a date and there’s a good chance it will become one.

The Date With Your Ex

In many ways this is like any first date. You want to look your best, make them laugh, and make them want to see you again.

With that in mind, pick a setting where you’ll be able to accomplish this. If your ex likes fancy french food, take them out to a nice restaurant. If they’re outdoorsy, go for a hike. It’s not rocket science.

Make sure this date is different than the other dates you two have been on in the past.

Don’t repeat your first date. Don’t take them to the Thai place you guys used to go every Wednesday.

Spring for something new and exciting. Go on a carriage ride through the park, go ice skating, or surprise them with a ticket to a sporting event.

Be Brand New, But Familiar

This is how you’ll use this date to win your ex back. Your goal is to be “brand new but familiar” at the same time.

Brand new but familiar is a bit of an oxymoron, but let me explain.

Consider the humble McRib. Frequent fast food patrons, such as myself, will know the McRib: McDonald’s signature barbecue-flavoured pork product pressed into the shape of a rack of ribs, served on a 5 and a half inch roll.

The McRib is nothing special; it’s a pork sandwich slathered with mediocre barbecue sauce.

But people covet the McRib because of its scarcity.

Be the McRib.

The McRib is only available for a short period every year and is liable to be removed any minute. That’s why thousands flock to McDonald’s every year to get the McRib: that comforting pork-adjacent flavour that is at the same time, new and exciting. It is at once both familiar and brand new.

I want you to be like the McRib on this date.

You need to remind your ex of all the things they miss about you. What makes you special and unlike anyone else they could find out there on the dating scene.

This should come naturally and organically when you two spend time together. Inside jokes, happy memories, and the familiar rhythm of your conversations are all things to draw upon to remind your ex what they’ve been missing.

Being brand new is about showing them that you’ve changed, that you’re willing to show a new side of yourself to them, and that you’re not the same old boring person that contributed to the breakup.

It can be as simple as getting a new haircut, and some new clothes that are different than what you used to wear.

Plus, surprise them with stories about what you’ve been doing while you were apart. Ideally you want your ex to see you making progress towards some goal. What’s a personal obstacle you’ve gotten over since you’ve been apart?

They important thing is that they see you differently. If you’re exactly the same as you were when you broke up, then why would they want you back?

Be Positive On Any Dates With Your Ex

Don’t dwell on the breakup. You’re past all that now. That talk will come if you decide to give things another shot but for now, don’t dredge up the past.

Think of it like any other first date. Would you bring up your last breakup? No, you’re trying to keep things light and fun.

The key is to show them that It’s been different without them around, but not worse. This means that their absence has had an effect but that there’s positive and negative aspects of it.

You’ll look confident and stable and they’ll see you don’t need them to be happy. It takes the pressure off of them to solve all your problems.

This date isn’t about trying to trick them into taking you back so try to calm down and not push too hard. (Click here to learn why you need to make your ex chase after you, rather than the other way around…)

Even if you’re extremely nervous (who wouldn’t be) you want to come off natural and relaxed. The more you can get them talking, the easier this will be.

Put The Focus On Them

We often become very goal oriented in these situations. Am I doing okay? Do they want me back? Am I doing all I can to show them I care?

Try to quiet these voices and just have an honest conversation. Chances are you have plenty of catching up to do.

Ask them what they’ve been up to since the break up. Ask them questions about themselves that you’ve never asked before and focus on really listening to what they have to say.

At some point, I want you to try to initiate physical contact. Don’t go for the kiss right away but touch their arm, rub their back, hold hands.

Touching is an extremely powerful trigger that will get them out of their head and seduce them in a way words alone can’t.

Ending The Date

If everything has gone as planned, there are two ways this date ends. Either you part ways on a good note or you go back to your place and get hot and heavy.

The key here is to be casual. If the mood is right, ask them if they want to go back to your place. If they say no, make sure they know that you don’t mind. Don’t pout or run away.

It’s okay if this date doesn’t lead to sex. It doesn’t have to mean anything other than they want to take things slow.

Either way, if you do all this right and they’re serious about giving things another shot, you’ve laid a foundation you can build upon.

Five Things To Avoid

Don’t ask them if they’ve been seeing anyone. This is a conversation you both want to avoid. You don’t want to come off as jealous or possessive.
Don’t brag. If you spend too much time talking about how well you’ve been doing they’re going to think that you’re trying to impress them.
Don’t push for the next meeting. You want this date to be self-contained. If you try to get them thinking about the next step, they’ll put their guard up, start thinking about the breakup, and stop having fun.
Don’t be a downer. Sure, it’s been tough and you don’t have to hide that but don’t dwell on it. They should see you making positive progress, not falling into a deep well of depression. That’s not sexy.
Don’t worry if it’s awkward. There’s going to be some awkwardness on both sides. It’s a weird situation. But awkwardness can be the key to getting their guard down. If you can push through it and make them laugh, remind them of how happy you can make them then you’ve got them back into the mindset of when you were together.

In my experience, if you can make them laugh, nine times out of ten you can win them back.

Jessica Boss

Jessica Boss is your trusted guide through the mysterious world of dating, relationships, and breakups. She's a 'romance geek', a regular contributor to numerous publications and journals, and an experienced relationship coach with a genuine passion for helping others create and maintain stable, loving relationships.