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 [email protected]. 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

Tuffy Luv Sez: Step Away From The Crap
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