He’s hooked up with all of his friends

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I've been dating a man for the past couple of months and everything has been going well so far. We're both in our 40s, never married, no kids. We met on a dating app and had great conversation before meeting in person and the connection grew from there. He's smart, funny, attentive and makes me feel special. I haven't had butterflies and excitement like this for someone in a long time. We're both taking it kind of slow because we've both been burned in the past but we talk every day during the week and see each other on the weekends (we don't live in the same town). We have had sleepovers and have started meeting each others' friends. He has a big group of friends who love to get together. There have been hiking trips, beach days, and backyard barbecues that I've started to be invited to. He hasn't introduced me as his "girlfriend" officially yet but it's clear we're seeing each other.

Recently I learned something kind of alarming through the “grapevine" – or maybe it was just one of his friends trying to warn me. He has had sexual relations in the past (or at the very least occasional makeout sessions) with what seems like nearly all of the single women in his friend group. Most of these people are still actively part of his social life and some have harbored unrequited crushes or infatuations with him as a result of these actions. Some of these women I've met. I don't know what to think about this and could use some advice as this is a new predicament for me. It's not that I don't trust him, but everything is just so new right now. I've been really excited about him and about seeing how this could continue to grow – but it weirds me out about being invited to get-togethers where I can look around and know half the women I'm looking at have had sex with the man I'm dating. It's weird and gives me the yuck feeling. But I still really like this man. I don't know if I can bring this topic up with him because everything is still so new and he also probably doesn't know that I've been told this information. I also don't want to seem crazy or jealous this early on. Do I even approach this? Is this a red flag? Does it need to be?

– Red flag?

He's in his 40s. If he's known these friends for a very long time, there's all kinds of history, I'm sure.

I can't make a judgment about his past. I'd only say that no one has told you that he cheated, disrespected a boundary, or anything that would suggest he's been dishonest with these women right? Yes, they might still be into him, but that's life.

I don't see a reason to bring it up right now, mostly because it's new information and the "yuck" feelings might evolve into a "whatever" kind of vibe. If you brought it up, what would you expect him to say? What would you be trying to learn? The better plan is to let things progress. Instead of imagining his past, consider his present. How does he treat his friends? How is he including you? Cleary he has no issues with bringing you around the people in his life. He seems comfortable, yes?

At some point, he might tell you about his history with these women. You'll have to decide whether to explain that you already know. I vote for honesty at that point – to disclose that someone told you, but that you wanted to get to know the group as is.

For now, give yourself time to see what all of this looks like. Pay attention to how he treats the people around him – including you. You say you trust him. That's important.

– Meredith

Readers? Would you bring this up? Was this a warning or some kind of challenge?