How do I break up with my boyfriend but remain friends?

He certainly doesn't deserve to be broken up over the phone, after two years. My best bet is probably Zoom, which he also doesn't deserve, but I can't get in a plane to tell him.


My boyfriend and I have been dating for almost three years. We met online and became really good friends. I had a huge crush on him, and he liked me back, to the point where he came to meet me halfway across the country. I thought he was the one – we had the same sense of humor, similar tastes, shared interests, similar knowledge of dumb stuff no one knew but us. He was – and is – my first real love. He is funny, smart, kind, caring, and always there for me. He makes it clear in his words and actions multiple times a day that he adores me and would do anything for me, and even though we stayed long-distance, we tried to see each other often (before the pandemic) and always talked about eventually moving in together (both of us met while in college and so we were pretty young to make these decisions, really the only factor besides having a job that prevented us from moving). This is the first real relationship either of us has ever had. With the pandemic, we haven't seen each other since March, which is also the longest we've gone without a face-to-face visit.

Like many people during the pandemic, I became unemployed, and he was my rock through it all. Without him to talk to, and call, and lean on multiple times on a daily basis, I probably would have gone insane. I consider him my best friend, someone I can talk to about anything and receive support and no judgment, and I feel certain he would feel the same about me.

I've had thoughts before about breaking up, usually some wild fleeting insecurity late at night where I can convince myself the next morning that I was being weird at 2 am. But over the course of our relationship, things became clearer to me that he might not be the person I want to be with romantically. He was always uncommunicative about aspects of his personal life, even as he cared and asked about me, to the point where asking him questions became like an interrogation. We don't have as much in common as I discovered I need: I'm a huge reader, I love art, music, movies, tv, everything, and he has literally no interest, and I mean any interest, in any of those things, although sometimes he will watch things with me to pacify me. But even that feels like coercion. He's also unmotivated; he's essentially living off his parents, never graduated college, and has no interest in doing so (to be clear, I am not a snob about higher education, but the career he wants requires it and his parents are willing to pay for it AND this is all stuff he didn't tell me until about a year and a half in. I also know that right now is not the time to critique someone for not having a job and for not wanting to go to school, but these were issues before the pandemic.)

I don't want to paint a bad picture of him; no one is perfect, and he has wonderful qualities too. He's never had to develop strong communication skills, and we've talked about this and I know he tries; I'm the person he's been the most open with, including family. But after two years of this, I feel like he's not going to mature or change, and I'm not going to be the person he changes for. I think he's comfortable where we are, even if I'm not. Because this week I began to feel with certainty that I had to break up with him, and I don't know how to do it or if I can do it.

He certainly doesn't deserve to be broken up over the phone, after two years. My best bet is probably Zoom, which he also doesn't deserve, but I can't get in a plane to tell him. But more than that, I'm worried about losing him forever. He really is my best friend, and he means so much to me. For his faults, we really do share interests that I don't find in other people; I just can't see myself spending the rest of my life with him. I want to be friends, but I'm worried he will just hate me forever. The one time I brought up "hey if we ever break up we'd still be friends right" he was incredibly upset I would even suggest breaking up. He's also going through a tough time right now and just started taking meds for depression, and I'm worried I'm leaving him in the lurch, even though it feels crueler to lead him on. I still want to be there for him as a friend, even a best friend, but I know it might be too much to ask. But as selfish as it might be to ask him to stay friends with me after I break his heart, losing this relationship in my life would be like losing a piece of myself.

I've been crying my eyes out for days with the stress of this, and there's a pile of tissues next to me as I write. I don't know what to do or how to do it without breaking his heart completely. The irony is that he is exactly the person I would go to with a decision/life-changing situation this big, but obviously I can't. I need...advice? reassurance? A hug? I don't know. But I need help.



Ok, you sweet, sweet, sweet angel of a human! This is all tackle-able!!! Not to worry!

The first thing I want to say is that there is no wrong decision.

I think you are ready to break up with him and it sounds like you have made your choice, which is so fucking hard to do, so I applaud the hell out of you. The hardest thing I’ve ever done is break up with someone; I hated it. So please know that I have the utmost respect for you getting to this point.

That said, no matter what comes next—if you do or don’t break up with him or if you break up with him and bungle it a bit or if you guys remain friends etc etc etc—there is no wrong choice. It’s like trying to crash your car in the right way. You can’t. It’s going to suck. Except you won’t die or anything. Sorry I used the metaphor of crashing a car. It was a bit extreme.

I want you to know and hear that you aren’t cruel for breaking up with someone. That is not cruelty. It might even be a type of kindness in the twisted way that being honest about not loving someone like that is kind, but you don’t need to try to feel positive about what you’re about to do. All I’m asking is that you feel as little negativity towards yourself as possible. People break up with people all the time. Relationships end. It’s R O U G H. But it is not evil. You are not doing something to him, you’re asking for something for yourself. And that something is a different future and a different present. Again, I am not minimizing the suck-age of breaking up with a person who probably doesn’t see it coming. I am, however, reminding you that you are not the bad guy. You aren’t responsible for staying with this guy the rest of your life just in case it might make him a tiny bit happier; that would be sick.

That said, you CANNOT ask him to be your friend after this. I’m sorry. I know it’s a standard part of some weird cliche world break up, but you two are not going to be friends after you tell him you don’t love him. Are you kidding? That’s like a job saying, “We’re not going to hire you, but you can still come in and do the work.” As someone else online put it, it’s like your mom saying, “The dogs dead, but we can still keep him.” UHhhhhh no thank you. I’m not suggesting that friendship in and of itself lacks value or that people cannot be friends with someone whose junk they’ve had in their mouth. Friendship is THE BEST. If I could only pick friendship or romantic love for the rest of my life, I’d pick friendship. I’m A HUGE FAN of friends. The problem is that you’re about to do some real damage to your relationship and then you’re going to ask him to pretend like you didn’t hurt him. It’s like driving a bulldozer through someone’s house and then begging them to keep living there because “don’t you remember all the fun times we had here? Don’t you love this house?” YOU CANNOT DO THAT. It’s not fair.

If—and it certainly might happen—you two ever are Friends-Just-Friends in the future, it must be on his terms. (Not that you won’t also get to have boundaries and say in what the friendship is like!) You cannot demand the good parts of the relationship you have with him currently and discard the rest. I know that’s not what you’re trying to do or meaning. I know you sincerely enjoy and love a lot of complex parts of him and that it kills you that there is not a version of the future with you two together romantically. But no one hears, “I don’t love you, but I want to be close friends,” and actually hears the complex truth which is something like, “Guess what? We are not romantically compatible, but I have come to rely on you emotionally and I still have love for you, but I am no longer interested in the hard (sometimes sexy) work of loving you.” They hear, “Put in work and get nothing good out of it.” Not that friendship with you is bad!!!! Again, friendship with you is a gift!!!! But not for someone whose heart you just broke.


So when you break up with him—and it sounds like you should/will/need to—here is something like what you can say. (Please make it your own words; he deserves that and so do you!): “Gerald, I wish I weren’t going to say this because I care about you so deeply and our relationship has genuinely meant the world to me, but it’s no longer working. I cannot see us being together in the future and I’m so sad that that’s the case. I’ve been trying to figure out a way in which we could fit together and I no longer see it and I have to be honest with you. I’m so deeply sorry because I know this will hurt and I know I’ll miss you being in my life like you were. I don’t think we have the same values or want the same things out of life and the difference is insurmountable. I care about you a lot and whatever you think will make this easier or better, I’m more than happy to accommodate*.”

*If he’s like, “It would make it better for you to sleep with me / stay dating me / etc,” then obviously that’s a no!!!! Accommodate within reason!

Do NOT give wiggle room for him. Do not say “maybe” or “I just…” or “I kind of feel…” use very clear language. Do not give him room to beg or plead with you to stay.

You can do this over Zoom; that’s fine!!!! BREAK UPS SUCK NO MATTER WHAT!!!! Breaking up with someone over the phone or on Zoom is fine. (If you actually have a conversation and say what needs to be said). I know that’s not conventional wisdom but if you’re more mad about the medium through which the break up happened than the break up itself… that’s bullshit. No one is ever going to like being broken up with, but sometimes you cannot be in the same place. It’s fine. It’s not a big deal. If you two lived in the same city and you did it over the phone… different story. But Jesus, it’s fine!! I swear. Zoom is very nice, but the phone works too. Just be open and communicative.

Do not lie, but remember that you do not need to communicate every flaw that you think he has. You can be vague and often it is a kindness. Even if he keeps asking “why” you do not need to be specific about your answer. I might get flak for saying that—some people are very horny for deep excruciating honesty—but I think I’m correct. (Of course I do!) My opinion is this: since you are no longer choosing to date him, your opinion of him is moot. You don’t get to give your dog up for adoption and then insist that the new family keep his name. Sorry!!! If he asks you why things weren’t working for you, you can explain your feelings, not his flaws. (Which are really just what you perceive to be his flaws).

As a note: I do not think you are a snob or shitty for being reluctant to have a future with someone who is not taking opportunities being given to them on a silver platter. I am very glad that he’s starting to take medication for depression. I’m sure that a lot of his choices in the past have been tied into his mental health; I am sorry for him that that happened. You do not need to stay around and keep dating him as a favor to his mental health. No doctor on earth prescribed that for him. Dating someone isn’t a favor, it’s a partnership.

I think you have tons of great reasons to break up, and I do think there’s some chance that the two of you become friends again in the future. I am begging B-E-G-G-I-N-G you to please have at least a few months where you guys don’t talk first because you have built your life together and that is not undone by staying together. It just isn’t. To give you one last terrible metaphor, imagine trying to get a bad smell out of your car while leaving a can of tuna sitting on the dashboard. It will not work!!!!

Please give him and yourself time and grace and space and patience. You will make new friends that fill the spots in your life that he has filled; I swear it works that way. I swear. I’m not asking you to never speak to him again, I’m just promising that you will be surprised by how the hole in your life that the relationship leaves will fill up, and how quickly it will begin to. I promise. You’ve got this.