Being Friends With Your Ex Is Impossible, Right?

Last night I went to go see Celeste and Jesse Forever — the new indie rom-com starring Andy Samberg and Rashida Jones that’s about a couple who, despite being separated, remain best friends. I have to admit that my expectations for it were low. I had read things about it being an anti-rom-com which, in Hollywood speak, typically means a lot of twee montages of a couple riding bikes and making mixed tapes for one another. I’ve found these so-called authentic movies about love to be more insulting than a mainstream Nicholas Sparks movie because they claim to actually give you an honest depiction of relationships when, in fact, they’re just as phony and saccharine as anything else. Last time I checked, relationships didn’t come with a Moldy Peaches soundtrack and couples didn’t do things like run around together in a water fountain all day.

To my relief, Celeste and Jesse Forever managed to avoid the shallowness that pervades most standard indie rom-com fare and actually showcased a relationship that felt uncomfortably real and engrossing. You cared about these characters. You understood the dynamic. You got why these two people fell in and out of love with each other but still couldn’t let go of the friendship even after all was said and done. At the crux of it, Celeste and Jesse Forever is about the foundation of love, which is always friendship. Your lover should always be, first and foremost, your best friend. If the relationship ever ends, it’s what you will miss the most. You think you’ll be missing the sexual aspects of it, and maybe you will, but above all, you will be mourning the loss of your best friend. You’ll miss the fact that they were your companion, your partner in crime, more than you’ll miss the sex. Sex can be replaced, sex can be picked up at a bar. Connections, however, are rare and can only grow with time.

Watching Celeste and Jesse Forever made me revisit the age-old question of “Can you be BFF with your ex?” In my experience, the answer has been no. I dated my best friend in high school and when it ended, I didn’t have the wherewithal to cut him out. Instead, we just resumed our close friendship without the sex for FIVE YEARS. Oh, it killed me and all my friends were just like, “Ryan, what the hell are you doing? He’s your ex. You can’t be friends with him.” I would dismiss them, saying that it happened back in high school so it didn’t count. We were older now, more mature, and could totally be best friends without it getting weird.

Wrong. So wrong. This is always wrong, right? When has this ever worked out for anybody? Maybe in your 30s and 40s when maturity is a real thing instead of something we PRETEND to have but it certainly doesn’t happen when you’re a 22-year-old psycho with little experience in relationships. Simply put, I lost my shit for five solid years. As long as we continued to be best friends, I was a damn basket case. Why? Because I had never had such a close friendship with another gay guy before or after and it screwed with my head. Our bond was so iron-clad that it made my feelings all smudgy. If we got along so well, why weren’t we together? Isn’t that what you should do with your best friend who also likes boys? Shouldn’t we just get married and be best friends forever?

Of course, it’s not as simple as that. It never is. But I did know one thing for certain: I couldn’t continue being best friends with him. I needed to move on and I couldn’t do that when we were still hanging out every day. It also screwed with my motivation to date and fall in love with someone else. For a while, I was content with just being best friends with him and not having sex. It adequately filled the void for me. Why look for someone else when I’m happy with this person?

These were the lies I would tell myself to delay doing what I knew was the only possible option, which was ending things once and for all. I thought that I was fine with just having our close friendship and didn’t need sex. Our emotional connection was enough for me! That, of course, wasn’t true. You do need sex. You do need intimacy. And since you’re not going to get it from your ex, you need to find someone who can actually fulfill all your needs.

It was one of the hardest things I had to do and I still miss the friendship. I know now that close connections, whether they be romantic or platonic, are hard to come by. But for the sake of my sanity and my own love life, I needed to cut the chord.  In my case, I couldn’t be close friends with an ex. It didn’t work for me.

Has it worked for any of you? I’m genuinely curious. TC Mark

Ryan O'Connell

I'm a brat.


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  • Lee

    I am actually friends with 2 of my exes, but the other 2 exes I could never ever ever ever be friends with ever. I think it depends on many factors (i.e. the nature of your relationship, how tumultuous the break up was, was the break up mutual, how much time has passed since the breakup, the experiences you shared throughout the relationship, etc). I don’t think there’s a yes or no answer, it depends on a lot of things.

  • AliceW

    I’m not really sure. I’d like to say it works but ask me again in 6 months to see if my mental state agrees with my rational/logical side. getting your emotions to coincide with your brain is a tricky thing

  • Sarah Moeding

    After about a six month to one year period where we need to hate one another, I almost always resume friendship with my former paramours, and often, it’s a closer friendship than it ever was when we were dating, because we have the understanding of one another at a deep level while also being in a position to comment on one another’s flaws without a chance of it leading to a lovers spat. Friends take that kind of criticism much better than lovers.

    • PowerMetal Princess♥ (@SinnyWolf)

      Yep, that was how it worked for me. We hated each other first, but at the end we are better being friends than being a couple.

  • tooloot

    After three years of desperately avoiding and ignoring each other at every social function after our break-up, my ex (who was one of my closest friends before we started to date) and I have started to reconnect. It’s uneasy and I think neither of us trust each other fully (yet) but we are beginning to establish what we had before we made an undying bond to love each other fully and forever (or until we both got so freaked out that we had to end.) It’s nice. Makes me realize I missed him… and not the sex. Just missed his presence.

  • nwairah

    Nope. Never. None for me.

  • sinny

    Actually yes, I’m friend of my ex and we have a healthy friendship, we call each other and visit each other often, I’m not only friend with him but with his family too as he is with mine.

  • Isabel

    Wow, i’m 22 and my ex is trying to be best friends with me. Mind you, he has a girlfriend with whom he has a very troublesome relationship with (who also knows I’m his ex and doesn’t like me at all, might I add). I also thought being best friends with him would work; we were friends before we began to go out. We like the same things, act the same ways, have few differences — like two peas in a pod.

    But as I began to look at new guys, I have noticed a change in him. He’s trying to peak over my shoulder to see conversations, he begins to think any negative status I put up are about him, he feels the need to tell me about his sex life if I tell him something I did with a new guy. I’m beginning to come to the same conclusion as you did: If I want to move on, I can’t have a bestfriendship with him. My fear is that whatever new thing comes my way will be tainted early on because of this bond I have with my ex.

    It will be a sad and difficult thing to do for me too. But this did comfort me. That even if its sad to let that go, I will at least have new things to look forward to — with no strings attached from my end.

    Great article!

  • youcouldbehappy

    when my ex and i broke up, he wanted to be friends and i wanted no communication. i was still in love with him so naturally i gave the friend thing a shot. it ended with us drunk dialing each other every now and then and that was about it. it even got so bad that i drunk dialed him while i was on a date. i was a mess and have no problem admitting that.

    so no, it didn’t work for me. but it’s all good. different strokes for different folks.

  • Miss Navarro (@LeelaChrista)

    My ex and I were together for 5.5 years (17-22 ages) … straight through.. no make up/break up BS… Lots of ups and downs.. We were kids at the end of the day pretending to know how to do an adult relationship.. fast forward 6 years, and he’s my best friend. We had to take a year or so after we broke up to heal and move on- no contact. I genuinely believe it’s possible for true friendship if the break up wasn’t due to some sort of betrayal…

  • Bark Muckerzerg

    I find that many people in there late teens and 20s still change too much, especially after a big life changing event a terrible break-up can be. I know I always have, and my ex’s have changed in so many ways that I simply can’t click with them anymore. People in that age group are too unpredictable, too afraid of connecting, attaching. They change, and so do we. And whether it’s us or them who pushed it all over the edge – I don’t know. Not that it matters, not at all; what’s done is dead. Personally, in retrospect, I always seemed to invest too much heart, mind and soul into the relationships to simply be able to move on. It’s part of having a obsessive personality. I still try to move away from that notion simply so I won’t be ‘hurt’ again (in itself a very terrible and ridiculous idea that I will never be able to fully act out on anyway), but when I truly, truly learn to love and trust someone, I do it with all my heart. I can’t help it. I’m just trying to enjoy the beauty of it to the fullest. Ain’t nothing wrong with that, right?


    Now here’s a sitch: Can you be friends with your ex who you broke up with for 3 years or so, when neither of you ever had any relationship after you broke up?

    I think it’s easier for people who have really moved on (meaning, both of them started dating again and whatnot) to say they can be friends with their ex, but what if both of you haven’t had any relationship/dates yet after you guys broke up?

    I mean, not having any relationship after the break up for n years, won’t that count for something?

  • Drew

    In my opinion, I don’t see the point in being friends with an ex. I understand that there is a connection that is hard to find, but that’s kind of the point. You go through these so-called real connections, you miss them, and you move on stronger. I still miss my ex, we were best friends beforehand. Do I think if I became friends with him now that I’d miss him less? No. Quite the opposite. The thing about people is that dynamics never change, so there is no way you can feel nothing romantic with an ex, no matter how minute it is. Do yourself a favor and let them go. With that open space for a new friend, you’re are opening yourself more to new possibilities and opportunities, ones that would never be present if that ex still resides.

  • a weary reader

    I’ve grown weary of these blatant product placement posts. I appreciate the attempt to weave it into a compelling story, but now I just feel marketed to, quite inauthentically.

    • Ryan O'Connell

      LOL, honey, this is NOT a sponsored post. If it was, it would say. We’re legally required to specify if it’s a sponsored post. Jesus, you readers are so paranoid park sometimes!

      • a weary reader

        thanks for the clarification, I apologize. Although I do think it is still a bit heavy handed with the movie promoting, mentioning the movie title four times, the actors once, and using a picture of the actors on the home page.

  • Only L<3Ve @

    […] Thought Catalog » Love & Sex Add a comment […]

  • AkR1209

    If you’ve completely moved on…possibly, but pretty much close to impossible.

  • Lexi

    I think its a total toss-up. I was married twice, husband number one and I have remained friends. We have know each other a very long time. After we were married, unfortunately, problems developed that we could not fix. He has helped me out financially, has kept me up to date on our mutual friends and for the most part, its been great. Husband number two is my worst enemy. We do not see each other or talk to each other at all. If for some reason we do, it is very uncomfortable and we always end up in a fight. Weidest thing though, married to #1 for 2 years (together for 12) married to #2 for 12 years (together 2, and we have a grown child together). People change. So I think it just depends on how severe that change is as to you being able to stay friends.

  • Jessica

    Both my boyfriend and I are friends with our respective exes. We both dated the exes for 7/8 years, from high school through college, and broke up post-graduation. In neither scenario are we BFFs with the ex, but we both get together once in a while with the ex to catch up. It works, I think, because we both understand the situation without getting jealous.

  • Morning Tempest

    It is not only possible but very rewarding to have a friend that knows you as well as can be, loves you in spite of your worst traits, and someone who wants to know you and be there for you but doesn’t need to be the only one in your life. 25 years ago I dated an amazing man, realized we were totally the wrong people for each other in a relationship but we were much better at being friends. We knew how to laugh at each other’s jokes, how to back off when needed, and how to tend to feelings carefully for each other. Now, we are both happily married to two of the best people on the planet and both of us are so thankful that our spouses understand our relationship.

  • JR

    My boyfriend is best friends with one of his exes. It can get a little weird sometimes, but since I know her outside of just being his ex, and since she has a new boyfriend, it seems to work out. They basically went right back to being friends after they broke up, and although their friendship will never be the same, it’s also no worse for wear.

  • Morning Tempest

    Reblogged this on Dancing with Fireflies and commented:
    A very nice post about friendship and how sometimes it does.. and mostly it doesn’t work out.

  • r4yne

    I dated my best friend back in freshman year in high school and it ended pretty quickly and we’re still best friends up to now; in fact, we’re so deep in each other’s bro zones, but I guess that doesn’t count because it was a few short months. I am good friends though with another one of my exes; there isn’t any awkwardness at all. So it’s totally possible to be friends with your ex, but it really depends on the circumstance of your relationship.

    • Hry


      • STFU HRY

        See screen name.

      • Rayne

        lol exactly why i said it didnt count

      • Rayne

        lol exactly why i said it didnt count.

  • Chosen Family

    Yes, I believe it is possible depending on the two people, the reasons for the breakup and the reasons for relationship in the first place. I have been best friends with someone I dated and we have been friends for 4 years. I do not think a romantic relationship was natural for us, but because we cared about each other and were young, it seemed like that was what we were supposed to do. We changed so dramatically during the relationship and the months following it that we were able to move past the petty stuff that we had been focusing on throughout our relationship. Perhaps the phrase “best friends” is an inaccurate description. I think “family” is more accurate.

  • ladylarisa1123

    I don’t know if it works Ryan… although I sincerely hope it does. I fell head-over-heels in like (I don’t dare call it love because then it would be to painful to even think about) with a guy who was my best friend and who felt the same way. It didn’t work out. We’re still trying to be friends, more or less, even though I feel like a piece of my heart was cut out. When I’m struggling the most with my feelings over the change in our relationship… the person I most want to talk to… the person who I know would understand… the person who could make me feel better… is him.

  • polkadot

    My ex-husband is absolutely my best friend! We were together for 13 years before getting divorced at 32. To make a long story short, we both realized that we simply wanted different things at that point in our lives. It absolutely hasn’t been easy at times, but we both love one another enough to go through the ups and downs that came with redefining our relationship.

  • Ellipsis

    That was me too, Ryan. It nearly ruined me. Made me bitter to a point that I became a cynic. I agree with Drew. Once the relationship is over, you should be open to new experiences and DIFFERENT people. Love is a state, not an action. You never entirely fall out of love, you need to let it go and move on. Though I have often thought about the what ifs of remaining friends, I remember how miserable the attempt made me in the past. It has made me stronger, but you can’t fling yourself against the elements with reckless abandon. You’ve got to protect and be responsible for the investment of your time and emotions.

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