Ask a Dude: Can I Date My Ex’s Friend?

[Got a Dude itch you just can’t scratch? Sick of getting the pity-eyes as you sift through the Self-Help section at your campus bookstore? Over wondering what those boys are thinking?  We got your back, girlfriend. Send your question (like, am I being a tease?) over to The Dude won’t sugarcoat it, beat around the bush, or any other weird cliche that means lie to you. Like a nice, juicy hot dog, he’ll be 100% real beef, 100% of the time.  So bring it on, ladies.]

Hey Dude,

I have a question about the supposed unwritten rule that guys can’t go after their friend’s exes. While me and my boyfriend were dating, I became really close with his best  friend, developing into a friendship some might call an “emotional affair.”

Anyways, for unrelated reasons, a few weeks ago, me and the boyfriend split amicably. I stayed close with his friend though, and not surprisingly, almost immediately, we jumped on each other. In fact, we’ve been spending time together as if we’re dating. We always had chemistry and since we had become so close emotionally, it feels like slipping right into an established relationship. Although we were always fairly honest about our friendship, we’ve kept this quiet.

We both feel pretty guilty about the situation (which is why we’ve held off on sex), but when we talk about how we should proceed, I get completely mixed signals. We both agree that we value our friendship, and want to continue to be close even if hooking up is totally off the table (and we are able to enjoying talking and spending time together without sex factoring in).

I’ve been completely up front that all I want is a casual summer fling without sneaking around (although I know it’s nicest to not be super public about it for the ex’s sake). He consistently says he can’t do this to his friend and that we should stop, but he’s the one that keeps making plans to hang out and then getting cute and cuddly and always making the first move. He has admitted he’s crushing and repeatedly said he can see himself seriously falling for me, but he doesn’t think it’s a good idea to get involved together.

I get the sense that maybe he is already falling for me, but is hung up on the fact that I dated his friend. However, I also acknowledge that it’s equally possible that he means what he says, and his actions (as sweet as they seem) are a result of him thinking with his dick when we get together.

I’m wondering how this “don’t get with your friend’s ex’s” thing works. Is there strict adherence? Any loopholes? Is it unreasonable of me to ask him to man up and talk to my ex if he wants to spend time with me? I don’t want to hurt my ex or break up their friendship, but it does seem unfair that we can’t have some fun together without all the guilt and secrets.

Think We’re In a Love Triangle

PS: I love Chuck!
PPS: That may have been a shameless attempt to try to entice you to answer my question…

Dear Think We’re In a Love Triangle,

Congratulations, your shameless attempt by appealing to my love for all things Bartowski (mostly Yvonne Strahovski) worked.

Your dilemma is a complex riddle with a very simple solution: take the hit.

BOTH of you need to talk to your ex/his BFF. This isn’t just about his relationship with his friend but your relationship with your ex, too. Because like it or not, if their friendship endures you then you’ll have to keep up some form of relationship with your ex. Fortunately, you sound like you’re still on good terms with the guy. Word of caution though, the longer you wait to have “the talk,” the worse this is going to go down.

Bros before ho’s is a commonly known term pertaining to bromances. There’s a lot of shaky ground to wade through when wanting to date your friend’s ex. Like it or not, most guys carry around some baggage about their former gal pals. We need time to move on and having her become a constant in our lives again makes that difficult.

Friends are our support system. We trust our friends and rely on them to help us get over you. By dating his friend, he could look at it as threatening part of his support system and losing two sources of trust instead of just one. Make no mistake, the end of a relationship is a loss and you’re new tryst threatens him with double the devastation.

Both you and your new boytoy need to sit down with this ex and break the news. Be decisive, concise, and clear. There’s no way to avoid confrontation if you want this fling/falling/relationship to go anywhere past what it’s become: a source of stress and frustration. You both need to let him know that your relationship is something separate of him but you understand it affects him. Then you need to listen. He may be angry and disrespectful. He might call you cowards and he might question what was going on between you two during your relationship. Take the hit. Be patient. Answer his questions. Disclose all the facts. Then you have to let the two friends make their decision. The bros first figure out the friendship and then you’ll know where the boytoy stands: with you or without you. Which should give you an answer as to whether this guy is worth your time or not.

Strange as it may seem, you’re the other woman to their relationship.

Getting your back bro,
Chuck Dudetowski



  1. Lauren H- The New Sc says:

    the biggest thing, in any relationship, is communicating, and while in this case, it would definitely be awkward, there's no way the relationships (any of them) can work unless all three people know where things stand. and I liked what the dude said about her being the other woman, because it's totally true and it's just one of those things you have to talk out – otherwise someone is just going to end up feeling like "the fat kid on team Bartowski"

  2. mtler says:

    I would never accept to be with my friends ex. Even if he tells me its fine, its not fine with me. I wouldnt like it to happen to me so i wont like it to happen to my friend.

  3. […] wondering what those boys are thinking?  We got your back, girlfriend. Send your question (like, 'can I date my ex's BFF?') over to The Dude won’t sugarcoat it, beat around the bush, or any […]

  4. […] Guy Bromances: For the most part, a college guy’s relationship with his broskies is actually kind of cute (if you get by the countless hours spent picking the ultimate Fantasy […]

  5. Another Dude says:

    I fancy one of my female friends, we got hot and heavy, but I figured one of my good guy mates liked her, sure enough a few days later they were an item, because I didn't ask her out right after.

    It sucked but it was the right choice, my good mate would have been hurt if I had hooked up with a girl I knew he liked, and I haven't even told him we ever hooked up. I've moved on and I'm dating someone else.

    I'm sorry for the question asker but really, in most cases a friend dating another friend's ex is considered a hefty betrayal.

    Simply put there are enough women out there that it should never lead to a situation where a good friend feels compelled to hook up with an ex unless he has cleared it completely with the ex boyfriend/friend.

    Generally mothers (obviously) sisters and ex girlfriends are off the table for friends, its an unspoken rule but an important one because the level of adherence to NOT SLEEPING WITH A MOTHER/SISTER/EX is the one reliable sign of either a good friend or a no-good ass.

  6. […] Guy Bromances: For the most part, a college guy’s relationship with his broskies is actually kind of cute (if you get by the countless hours spent picking the ultimate Fantasy […]

  7. Shiroichi says:

    …If you're only looking for a summer fling… try to find another one… I think it's better to let the two guys be friends than for you to have fun for just the summer…
    I know I'm late in answering this but for all the other girls that will read the post… Think about what you may be breaking and what you would have in return, does it seem fair?

  8. Cecilia says:

    I think that most of the time even if you ask a friend whether he/she`s ok with you two being together…he/she is probably lying…. Just don`t do it! Go out there,and find someone else.

  9. Helene says:

    What about if your ex and the guy you like aren't really good friends, rather acquaintices? I've been living in a virtual hell with my ex, we've been off for two years but have been living together for the house and financial reasons etc. I just want to find someone I get along with, and it happens to be one of his old workmates! We've got so much chemistry and things in common, it almost feels like fate, I don't know should I cross the line for love?

  10. Greg says:

    Why do people feel the need to look for emotional stability with someone that is connected in a way with heart ache. People have to remember….. there are.. LOTS AND LOTS AND LOTS of people in the world! You have your own friends and your own life. If you become emotionally attached to a ex's best friend then you have always been, subconsciously. Its not about rules. Its not about loyalty. Its about what you think your worth. You have take a step back and remind yourself that what you doing or thinking isnt the best choice for anybody. You have remember that your also vulnerable. You did the ditching you got ditched either way you are still lonly and need emotional or physical comfort. You have to have time and clear you mind. Approach with a clear mind. Months or years later. Love is always waiting.

  11. Patience says:

    I tink dre is not tin rong in datin yuh ex friend, especially wne u hv broke-up wit yuh boyfrd. Cos u dnt knw if ur ex frd cn extend d relatioship 2 marriage.

  12. Josie says:

    I NEVER would have thought that I would have had feelings for my ex's best friend but it just happened. We are keeping it a secret for now and it sucks, but I am willing to make the sacrifice for the time being? We figure give it a couple of months and then we can go from there….. the worst part about it is that we can't ever be anywhere together if we have mutual friends there because we don't want it to get back to my ex…… I just wish I had met his best friend before him and then it would be perfect……..

  13. safire33 says:

    What if it has been 5 yrs since you broke up, have a child together, & the person you want to date, coincidentally, turned out to be 1 of your ex's friend of a friend, that you never met before, and you only recently found out they knew each other? My ex has told me to stay away from his so called friend, & has told him to stay away from me. I don't understand what the big deal is.

  14. Beth says:

    I broke up with my ex a year ago. I think i only got with hin at a time i needed someone anybody. but he loves me or rather thinks he does. I have recently fallen for his supposed best friend. when we were together he never hung out with this guy. he knows we are friends and constantly asks his friend if he has heard from me. me and the friend did n’t intend to have feelings for each other but turns out we are veru much alike. but of course the friend says nothing can happenbeca use of his friend. to make matt ers worse we all work together. honestly though if my ex dated one of my friends or even my sister i wouldn’t care. it wouldact ually make me happy that he has finally moved on. but is it fair that i cant even find out how much his friend really means to me because he cant move on? i haven’t been able to find one problem between me and his friend. other than this. the friend has even said we never disagree and things cme so easy between us. the whole thing just sucks

  • You Might Like