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He’s hooked up with nearly all of his female friends

‘Most of these people are still actively part of his social life’

Love Letters

Love Letters

Q. 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. 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’ve had sleepovers, and have started meeting each others’ friends. He has a big group of friends who love to get together. I’ve started to attend their hiking trips, beach days, and backyard barbecues. He hasn’t introduced me as his girlfriend yet, but it’s clear we’re seeing each other.


Recently, though, 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 to be at get-togethers where I know that half the women there have had sex with the man I’m dating. It’s 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 he probably doesn’t know that I’ve been told this information. Also, I 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?


A. 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, a few might have had romantic feelings for 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 did choose to ask about his past, 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? Clearly 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.



This would not work for me. I imagine it would be fine for some people, but it sounds like you are not “some people.” My guess is that he’s a world class player that knows how to get what he wants from most any woman.


^I’m torn between this and he made out with a few of them in college. First instinct was same as yours though. I think it might be too early to tell. I wouldn’t say anything, just be more aware of the interactions of this group and his actions.


I know that you have the “yuck” feeling right now but it sounds like you really like this guy and he is treating you well. I think you should give it some time.


You said you’ve been “burned” in the past (who hasn’t by age 40?), so consider the idea that you might be looking for things wrong with the relationship to protect yourself from potentially getting hurt again. Personally, I think it’s weird that a “friend” of this guy would “warn” you about the making out — seems kind of like sabotage. Does this friend plan to inform every date this guy brings around? Does “friend” not want the guy you’re seeing to find happiness in love? I question that friend’s loyalty and the quality of their friendship if they’d be so quick to plant seeds of doubt in your head.



Nothing in this letter suggests this man is trying to “hide” anything — he’s including you in his life, and with these people. Everyone has a past, including you. His past is none of your business unless/until he makes it your business, and vice versa. By the rest of your letter, I’d be more concerned about who told you this information and why.


Go with the flow. Chill out. This is a New Thing. You’re doing fine already, and so worrying about the behind-the-scenes back-in-the-past hookups is only going to ruin a budding relationship before it really has a chance to be a relationship.


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