Dating my ex’s friend: Friends with benefits

Other questions about FWB (“Friends with Benefits”) and Booty Call: 

Are we “friends with benefits” or does he want something more?

Booty call or relationship trouble 

Divorced and now online dating: Am I booty call or more?

I suggested friends with benefits; did I just dig myself into a hole?

Friends with benefits; why me?

Friends with benefits? 


Dear Guys,

This is kind of a long story but I really need some guys’ opinions on this. Most women can rate their friends in their life and this boy is my 2nd best friend in the world. I would do anything for him. We knew of each other because of mutual affiliations but didn’t become friends until I started dating his friend. During the time I dated his ex we became close friends. But after being with my ex for 4 years—with all of us being part of the same circle—the break up kinda made things weird between the whole group.

Now for the hard part. This guy and I have always been very attracted to each other and are super comfortable and trusting of each other. A couple of months after my break up the sexual tension between us became overwhelming and things started happening. We would both try to stay away from each other but we attend the same university and see each other every day so that was really hard to do. I feel horrible because I don’t want to get between him and his friend (my ex) and he feels guilty about it. But whenever we see each other it’s really hard to keep things platonic. And as if that wasn’t bad enough I’m scared that these feelings are going to morph into romantic ones especially when he has started saying and doing some really sweet things. (And I really like him) And even though these thoughts don’t occur often, every so often they will pop up. He has expressed that he wants me not just because of my body but because it’s me. Things have been normal between us despite all sexual relations and none of our other friends have noticed anything yet. He is too important of a friend for me to lose. I want to stop because I don’t want to cause problems between our groups of friends but I do not want to stop at the same time.

I hate drama but “OMG” I love how this boy makes me feels and it’s getting harder to control this. And I’m also curious about how he feels about me, but I’m way too scared to ask. I don’t know what to do.

Please any kind of advice will help.


Dear Flora,

Thanks for your question.

You’d be surprised; this type of situation happens more than you might think. And it makes sense in some ways. When people spend a lot of time together intimacy happens. This intimacy can be the friend variety, it can be the romantic variety, or it can be something in between. While you were dating your ex you were also getting to know this guy and forming a strong bond with him. You can’t help it that he happened to be good looking too. So what we’re saying is, you should stop beating yourself up over this. Sure you might feel guilty, but this makes perfect sense, and we see nothing wrong in you wanting a relationship with your ex’s friend now that the two of you have broken up.

However, we’re not so sure if it makes perfect sense for your “friend.” He stands to lose more than you if the two of you are “found out.” (And we’re not so sure your friends and his friends don’t already suspect something’s going on between you. People can smell that kind of thing a mile away. No, we’re not being literal here, but we are being serious.) He will likely lose his friend (your ex) if the two of you continue to move forward. There’s a kind of an unwritten code between guys which states: Guys don’t date their best friend’s ex-girlfriends. And most of the time this isn’t difficult to abide by because most guys don’t like the idea of dating a woman their best friend has had sex with. However, like we said before, it happens more than people might think. So basically your “friend” has some serious thinking to do. He is going to have to make a choice between you or his friend (your ex), unless your ex is one of those super understanding guys. We don’t know any ourselves. (Side note: Sometimes after a very long period of time it’s okay to date a friend’s ex. This would be years though.)

Back to you.

If you are really into this guy we don’t see anything wrong with seeing where it goes. Because if you don’t, you’re always going to wonder what would or could have happened. And there’s nothing worse than regret in this life. We’re not guaranteeing it’s going to work out for you, and we’re not guaranteeing it’s not going to get messy or even ugly. But on the flipside if it does work out into a long term romantic partnership—that sounds so formal, but you know what we mean—then it will all be worth it. If it doesn’t work out, you can at least feel good that you took a chance on love.

But this all comes down to communication. You need to tell your “friend” how you feel and what you want. He’s not a mind reader. And based on what you say he very well might feel the same way about you. See what his reaction is and see what his take on the situation is. If the two of you decide to move forward with a more serious commitment you might want to think about calling your ex, or meeting with him, and explaining the new situation. (Yes, this will be hard and not necessarily pretty, but at least he’ll hear it from your mouth.) Your friend might want to do the same, although we wouldn’t want to be present for that. (Just kidding…kind of.) In general we think it’s best to be open and honest with the people in your life.

But what you shouldn’t do is continue what you’re doing now. If you’re not going to be serious about this relationship you should stop the “friends with benefits” thing immediately. In the end that’s not going to be good for anyone involved, especially you.

Good luck. Feel free to leave us a follow up comment, or ask us a follow up question. (In the comments section here)


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