Dating my ex’s friend: Is there a line that men won’t cross?

Dear Guys,

I have mixed feelings about how to proceed with a guy I like. (Or if I should at all) This guy and I have mutual friends, in fact, he is my ex’s younger brother’s friend from childhood. My ex and I started out as friends in college and still share tons of mutual friends. (I know, tricky territory, but it’s ok at this point). That’s the reason I know this guy in the first place. But we didn’t actually meet until after my relationship with my ex was pretty much over. Still, we would see each other at mutual friend’s events, we flirted, but nothing significant. As I got to know him, however, I really liked him and the feeling has grown this last year.

I haven’t been with my ex for over five years and now he has girlfriend of two years. This guy and my ex aren’t particularly close but have casually known each other for years. However, this guy still says he’s uncomfortable with the idea of crossing that “line” because he knows him. I would have let it go and taken him at his word, but then, over the past year or so, he would ask to come over whenever he was in the neighborhood and be super touchy and flirty with me. Then, last weekend we ended up at his place after a show we both attended. It immediately started with light flirting and then it got hot and heavy, although more heavy touching rather than kissing. He said he was having a hard time controlling himself.

After a while he admitted, “I guess there’s just a line a don’t want to cross… but maybe.” And the maybe was followed by a “What if?” But since he seemed so conflicted I ended up leaving. He apologized for putting me in a weird position but I let him know that I liked it and wouldn’t mind doing it again or even crossing the line further.

So the question is, what to do next? Do I drop it despite the fact that I’ve been continually impressed (and now turned on) by this guy and find another fish in the sea? Or do I take his actions and excitement about me and try and make a next move? I need advice… I like him, but I don’t want to freak him out and scare him off by coming on too strong.


Dear C,

Thanks for your donation. We do appreciate it.

We can see why you’re confused. Clearly this guy is attracted to you. Certainly sexually, although we don’t doubt he likes hanging out with you too.

Why isn’t he willing to take the next step?

There is an unwritten rule that men have. Typically we don’t like to date anyone, or sleep with anyone, who our friends have slept with. One, we see it as disrespectful, and two, we don’t like the idea of our friend having “been there” already, if you know what we’re saying. We know that probably doesn’t make a lot of sense to women, but the idea of being able to see all too clearly—yes, guys have a way of visualizing that sort of thing—the man that has come before us, is not very appealing, and actually downright bothersome. We prefer ex’s to be anonymous, that way aren’t able to conjure up an image that might make us queasy.

That said, if a guy is totally smitten with a woman, he might be able to work past both possible rules/issues. First, he might approach his friend and tell him his intentions, and ask for his friend’s blessing. (Not that he needs it. But guys like to know that everything’s cool. The last thing they want is a bro-conflict.) If his friend says it’s cool, and the guy actually believes him—guys don’t always say what they mean—then he has to decide if he’s okay with the second issue—the fact that his new girl slept with his buddy, or more pertinent, that his buddy slept with his new girl.

But in your case, since there are two degrees of separation—a younger brother of a friend of your ex—we’re wondering if your guy is using the “line” as a way to keep you at a distance. You see, guys know what they want quite quickly. If he saw you as having long-term relationship potential, then it’s likely he’d blow off any rule and just go for it. But if he sees you as someone he wants to sleep with, but not someone he wants a relationship with, then he’s likely using the guy code to keep you at a distance. Which means, he’s likely a good guy who is conflicted.

Our advice: Let him be the one to take any initiative. It’s possible he’s an upstanding individual, who’s totally smittien with you, and just confused about what to do. It’s also possible, he’d love to sleep with you but nothing more. Drop some hints, make it obvious what you want, but don’t make it easy for him. He’s a guy. Let him be the one to move this forward.

Last Point: Don’t let this devolve into a FWB—Friends with Benefits—arrangement. That won’t end well. They never do.

Good luck,


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