I (30M) have been dating someone (29F) for almost 3 months now and it is going great. But, I am worried about bringing up that I was previously engaged for a short time a few years ago.

We haven’t spoken in much detail about our previous relationships so far, just have mentioned that we both had long term things at certain points. This conversation was on our second date and it didnt feel right to bring up a previous engagement at this time. But there hasn’t been another moment we’ve spoken about past relationships and now I’m worried that I have waited too long?

Should I have said something then?
Should I still be waiting until it comes up more naturally somehow? It seems hard for that to happen about something that I don’t necessarily want to talk about and have anxiety about this person that I’m really excited about reacting negatively towards

5 comments
  1. I’d just wait until it comes up naturally, obviously I can only speak for myself but this isn’t some big revelation that would particularly concern me. Basically you were in a serious relationship and it didn’t work out

    OK

  2. I don’t think it’s nearly as big a deal as you seem to think. I’d argue she might see it as a positive since a 30 yo that never came close to marriage would be a red flag.

  3. sounds like a 3rd date topic (when baggage, history of note, is revealed)

    (you’re not posting previously engaged on your dating app profile? might draw interest like flies to honey — finding a fellow who’s almost ‘gone the distance’ has its own appeal)

  4. I’ve been with my man 6 years and I don’t know if I have explicitly stated my ex and I were engaging or not. it’s not like he left me at the alter, I mean I had made some plans but the wedding was still like 8 months off

    idk it just never seemed really important idc if he was engaged to his ex or not

  5. You’re overthinking this. Bring it up at a time when it’s natural in the conversation. This is not at all in the same vein of, say, having kids, which is something that should be disclosed immediately or almost immediately.

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