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How To Talk About Your Ex On A First Date The Right Way | A.K.A, how to open up the ex files.

The Right Way To Talk About Your Ex On A First Date

Aka, how to open up the ex files.

Talking about your exes on a date is actually a good idea, as long as you do it the right way.

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The only thing worse than your ex is an ex of the person you’re interested in. You know this, and I know this. So what do we do on a first date? We avoid mentioning our exes like the plague. But you, me, or someone we find ourselves on a date bringing up their ex does not, I repeat, does not mean the prospective relationship must go to shit.

There’s a happy medium between total transparency and total repression. Details about previous relationships can be helpful for new partners: A woman needs to know if her boyfriend had ever dated any mutual acquaintances. And she definitely needs to know if he broke up with his last girlfriend because she wanted kids and he didn’t. She does not need to know how great the sex was.

So yes, tell the new woman/guy you’re seeing about the time you got dumped but do it right.

“I don’t think it’s a bad thing,” says Susan Winter, relationship expert and author of “Breakup Triage: The Cure for Heartache,” of nodding to an ex on a first date. “It’s good that you have relationship history.” Letting someone know you have an ex shows that you’re a human with human experiences who has human connections. No shade to people who have never been in a relationship but, personally, that makes me more nervous than someone disclosing information about their ex. Of course, there are better ways to share than coming in hot with, “Hi, how are you? By the way, I just broke up with my boyfriend.” 

“The purpose of an initial meeting is [to determine], do we like each other enough to explore this?” asks Winter. Listen, we all have our own shit, but “you don’t want to present [as] a wounded person,” she says. “You want to, at [the very] least, show that there is space [for a] new person.” Whether a date asks you about past relationships or the topic comes up organically (which, a lot of the time, it does), respond with one or two sentences that give the person enough information without going into too much detail.

You just got out of a long-term relationship.

If you’re fresh out of a long-term relationship, you may even discuss the topic pre-meeting in real life. If not, there’s a fair shot it will come up on the date because it’s a major part of your current reality. Still, you need to be careful what you say and how you say it. “Always [try to] frame your experience positively,” says Winter. “It’s important to begin a new relationship on fresh soil. You [want to] relay the story of what happened in a measured, rational manner.” The “what happened” shouldn’t be a chronological breakdown of where things started to go south accompanied by spreadsheets and flowcharts. (Please, no spreadsheets.) Too much information too soon can be detrimental. Give answers, but don’t go into specifics, says Winter. 

If it’s too difficult for you to edit down your story, consider where you’re at post-breakup. Are you still replaying your feelings of victimization, betrayal, and anger? “Harboring these unprocessed emotions serves as a red flag to any prospective partners,” says Winter. In that case, you may not be quite ready to start dating again. To get there, work through those emotions by getting closure (if you can), talking it out with people you trust, or giving yourself more time to heal.

Be cool.

Wait until at least the third date, and slide into the subject obliquely. A friend of mine recalled a man who segued into the ex conversation really early on in their courtship, while they were discussing a TV show. “How long is too long to keep using an ex’s Netflix login?” he asked her innocently, launching them into a mature discussion about their dating histories.

Never ask your partner how many people she’s been with.

Even if she does answer with a number instead of a glare, there’s no way for you to respond to that information without sounding judgmental.

Don’t be too negative.

Describe your ex like you’d describe a former boss during a job interview. If you tell potential employers that your last boss was a huge jerk, they’re going to assume that you’re the jerk. They’re also going to be on their guard: If you talk about your last job in negative terms, they’ll worry that you’ll talk about them in negative terms, should things go south. So it is with exes. Trashing your ex won’t make your new partner feel less threatened, it will just make you look like a jerk. Instead of saying “We broke up because she was crazy,” be vague and neutral: “As I got to know her better, I realized she wasn’t who I thought she was.”

You’re still hung up on your ex.

The fact that you’re pining for your ex isn’t an easy thing to keep hidden (people aren’t as dumb as we think they are). “We can’t be perfect. We’re going [on dates] because we want to find somebody new,” says Winter. “We still love our ex but it’s not going to work out, so we have to move forward.” If the conversation shifts and you start talking about relationships and why things ended, all you need to say is something like, “It was really rough on me, but the good news I’ve had some wonderful relationships in my life and I’m glad that I’ve learned how to be a good partner.” 

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But don’t be too positive.

The person you’re seeing probably already knows about, and feels threatened, by your old girlfriends. Before I go on a date with a stranger, I do a comprehensive background check. I inspect her Facebook, in case she likes lame music or racism. I peruse her LinkedIn. And, of course, I study her entire Instagram. By the time we meet for our first date, I know that in recent years she has dated one guy who looks like Kelly and another guy who looks like Israel. I know that the Kelly one went to Yale University and runs a gym. I know that the Israel one teaches modeling and is still on good terms with my date’s mother. In short, I know just enough to feel insecure. The second you say something flattering about your ex-boyfriend I will begin to obsess over it.

You’re friends with an ex.

“It’s wonderful that you’re still friends with your ex, but this can cause unnecessary concern for a new person entering your life,” says Winter. If it were me, upon hearing this news, I’d spiral into another dimension. So, you need to be strategic about what you do or don’t disclose. Have you decided if you even want to see this person again? Is this piece of information crucial for them to know at this point in time? Is it absolutely necessary that they be aware that your ex comes to your pre-games sometimes? Probably not — at least right now. But if things do get more serious, be honest. Otherwise, you risk spiraling down an unhealthy track of secret-keeping.

No names!

I briefly dated a lady who talked often about her ex-boyfriend, Danny. (So often, in fact, that I wasn’t at all surprised when they got back together a few months after we stopped seeing each other.) When she told stories about Danny she always referred to him as “D,” like we were all buddies. When you talk about your ex, refer to him/her only as “my ex.” That way your date can maintain the illusion that you’re so enraptured by his/her carnal gifts that you’ve not only forgotten all but the most boring details of your old relationship, you’ve even forgotten their names.

…And some general don’ts.

  • Don’t dwell on the topic, either. Say your piece and then move on.
  • Be careful about including your ex in your stories. If your date asks if you’ve been to London and you have with your ex, you don’t need to mention who you went with — just say, “Yes, I went for a week a couple of years ago.” The only thing that [giving those details] does early on is make the new person feel inferior.
  • Don’t talk about how much money he/she has or made.
  • Don’t talk about how they handled a particular situation. In general, you should avoid direct comparisons between your current boyfriend and your ex. Don’t say, “Well, my ex would it do this way and it was way better.”
  • Don’t talk about the size of his manhood or her biggest fetish. This should be obvious, but guys don’t want to know anything about the other guys that have been intimate with their current girlfriend. On a related note, don’t talk about weird things your ex-girlfriend liked to do in bed; that’s why you have boyfriends. Even if you’re trying to make your girlfriend laugh by trashing your ex, she doesn’t want to hear the details.
  • Don’t talk about how your friends liked him/her. It’s already hard enough for a him/her to get on the good side of your friends—your current boyfriend/girlfriend doesn’t need to hear about how much your friends liked your ex. Hearing that would be a real hit to their confidence when their trying to make a good impression with your friends.
  • Don’t mention every gift they bought you. Trust me, your new boyfriend/girlfriend will go out of their way to hate anything they knows an ex gave you. Yeah, it’s petty and childish, but that’s how we roll sometimes. Just tell a white lie and tell them that every gift you’ve ever received came from a now deceased grandparent. It’s believable and will make them feel better.
  • That you still love/hate your ex. Never tell your boyfriend/girlfriend that a part of you still loves your ex. You also don’t want to overcompensate by saying something like, “I’m so over him/her.” You know who’s over things? People who don’t feel the need to say “I’m over it.” Don’t mention that you hate him/her either. We all know there’s a thin line between love and hate. If you mention how much you hate your ex, we’ll get a little suspicious.

Though we may feel awkward talking about the past, perhaps we shouldn’t. It’s not a con that you’ve had a breakup [or have an ex] — that means that you’re available for a relationship because you’ve left one. People’s main concerns when it comes to discussing exes are how long it’s been since you were together and whether you still have feelings for them. They, quite understandably, want to know the coast is clear to minimize their chances of getting hurt. If you establish that the past is the past, you’ve done your part. 

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