I had a first date with a woman today and we hit it off and immediately setup a second date! So this is the real first date I’ve had since I’ve been divorced and didn’t bring it up not to sour the evening.
I’ve heard some conflicting advice about how to do this.
Should I only bring it up if past relationships are mentioned in the future?
Disclose it straight out?
Casually sneak in into a conversation?

I really don’t want to withold it from her if it turns into a relationship, but when have you been in this situation, what did you do, and what happened?

18 comments
  1. I’m old enough now that people assume I’ve been married at least once (and they’re right), so it comes up on the first date. Inevitably I next get asked why it didn’t work out. Again, this is a date, people are trying to determine my character. I explain I don’t like to go on at length but my wife had an affair. Inevitably the next step I get asked is if I have kids. I say no, but I wanted them.

    Sometimes I’ll add little flourishes as necessary, or people will have follow-up questions, but this is basically the gist. This conversation is pretty inevitable, and I’ve never not had this conversation on a first date, and I’ve become very practiced at it. There’s no point in hiding things that are going to be coming out anyways, and it’s an opportunity to talk about things that have defined my character.

  2. i never had kids or owned property together, felt just like a long expensive breakup.

    i wouldn’t deny it but idk why it would matter to bring up soon?

  3. Sooner rather than later. I was dating a guy and he didn’t tell me until the 3rd date. I was pretty disappointed bc he should have disclosed it right away or even on his dating profile. It’s not a matter that should be delayed in communicating.

  4. Previous relationships should come up within the first few dates, regardless of the method. On your next date, you could steer the conversation in that direction without necessarily being blunt about it.

    Too many times in the past have I found out that someone was either divorced, just out of an LTR, or still talking to their ex a few dates into knowing them. I get why people don’t disclose those facts on OLD, but it’s taught me to bring it up early.

  5. If they don’t bring it up within the first few dates I usually ask them what they’re most recent relationship was like or something. And then discuss mine

  6. I don’t think anyone has the right to know and coming from a country where the word privacy has meaning I find this intrusive tell-me-everything culture is a bit disturbing.

    I think it’s a difficult topic if someone does directly bring it up, I don’t know if there’s a way to deflect it other than having a talk about exclusivity. (Which just feels like a childish thing to do on a first date but that’s me.)

    Better to play it by ear, if you share but they don’t then that’s their boundary and if your boundary is them not talking to their ex then say it and vice versa.

  7. The sooner the better. I was seeing a guy for a few months before he told me he was divorced and that he still takes care of her kids (they weren’t his kids, just hers)

  8. I always ask now whether someone is divorced before meeting as this a dealbreaker for me (ie – not interested in dating someone who is separated, too much drama IMHO)

  9. I used to disclose it early because of the same anxiety you’re having — I felt like I wasn’t being honest or something or I was withholding info.

    I’ve just learned that it’ll get brought up within the first few dates because everyone inquired about your last relationship on the first few dates or just through texting.

    Don’t stress about it!

  10. It’s not something you need to “disclose”. It’s a part of your past that will naturally come up in conversation at some point. Don’t worry about it.

  11. I think you are misunderstanding the advice.

    The general advice is not to talk about your previous relationships during the date. But, to say that you had one and it failed it is fine :). Just don’t go into details.

  12. It depends how long ago your divorce was? Like if it’s a month ago, probably during the texts before the second date.

    If it was years ago, casually bring it up by the fourth or fifth date.

    I dated a guy for several months. He wasn’t the romantic type, so I forgive him. Thought that dating was new to him. After 4 months, he told me that he was married twice and was engaged for 4 times. After that, I pulled back and only expected noting from him and eventually we broke up. (We were together for seven months)

  13. Mine comes up naturally because I moved cities during it. So when people ask why I moved, there’s an easy opening to discuss the breakup. I don’t have kids, I’m not bitter, and I not actively engaged in any kind of dispute with my ex so I could probably avoid discussing it longer, but I don’t know why I would other than the reason I discuss in the next paragraph. No one has reacted negatively to it. Maybe because of all the factors I mentioned above. 😉 Because I’m still connected to my ex’s family socially, it would come up eventually in conversation I’m sure.

    I do struggle with the “why” of the marriage ending. In my case, there are basically two major reasons I felt divorce was necessary and I am reluctant to discuss one of those reasons for what many people would agree are valid concerns if they knew the situation. Since I’ve been dating casually, I don’t feel the need to disclose every detail of my life to anyone, but I wonder at what point I would “need” to disclose more.

    I would say that I “stumble” a bit on my words when discussing my ex, so smart people get that there’s something I’m not saying. And smart people also realize their might be a reason for that and no one has really pushed super hard for more info. Again, it’s casual dating. I think the situation would be different if it was a serious relationship. That’s a bridge I’ll cross when I get there.

  14. I’m someone who would ask about it before the date bc it’s a dealbreaker for me, but if I found myself dating a divorced man, I would say just be straightforward and say it when it’s bothering you. Don’t wait for an arbitrary number of texts or dates, hah.

  15. What’s the big deal if the divorce is finalized and there are no kids involved? Just handle it like any other long-term past relationship. Mention it when the topic of dating experience comes up.

  16. Whatever you do, say it in person so there’s context. Digital disclosures can come across in weird ways.

  17. Unless you just got divorced, that info isn’t important to me and it’s fine if it just comes up through the, eventual, organic discussion of past relationships.

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