I (29F) met this guy (33M) through OLD and we’ve been talking for a few months. We live in different states so haven’t been able to meet yet but we’re having a first date (dinner date) in 2 days.

During these months though I’ve noticed (in the past 2 months) that he hasn’t really asked much about me and I realized I know more about him than he does about me. Our video calls have been great with various conversations and usually lasts for a couple hours, but I’m not sure about this one thing.

So since we’re meeting up I’d like to ask for questions I can keep in mind to ask that would help me gauge what a relationship could potentially look like between us and just more practical & personal conversations. We already talked about our general & personal wants: I.e. relationship, family in future etc.. We have similar hobbies, and ways in which we spend our time, but I still feel like there are things I’d like to navigate.

Ex: is it too forward to ask about his past relationship (he’s divorced) and the details of that? what should I keep in mind to bring forward?

Maybe I’m just nervous cause I haven’t talked to a guy for as long as I have with him, and he’s been quite consistent with me. I haven’t had a proper date in almost 10 months just don’t want to overthink it.

Thanks in advance!

1 comment
  1. Speaking as a divorced man, I can tell you that we’re not a monolith. Men are divorced for numerous reasons and have had different experiences. There is no specific list of questions you can ask that will tell you whether he’ll be a good partner to you or anyone else.

    A man who’s wife cheated and left him is going to have a lot of different experiences than a man who asked for a divorce because the stress was too high.

    That being said, if the conversation is going well, go ahead and ask about what happened. Try not to pry too much into the details, but getting a general idea is absolutely permissible. But unless he states that he cheated, there’s really nothing you can take away from that which should give you a solid idea on whether or not to keep seeing him.

    Try not to be too pushy, but try to read in between the lines in his explanation. If you enjoy his company in person, I would recommend that you agree to see him again, and as you get to know him better, you can probe little by little about the reasons for the divorce.

    A man who is honest with himself will probably volunteer some information as you continue to see each other.

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