I've been casually dating a guy (let's call him Tom) for a couple of months. At the beginning, I thought things were great but I wasn't looking for anything too serious. The last few weeks, I've felt nothing more than friendship towards him but he feels very strongly about me. In addition, I've been hanging out with a group of co-workers quite a bit and think I am developing feelings for one of them.

I told Tom about all of this and how I am thinking of ending the relationship so as to not waste any more of his time, but he seems to think that I'll come around eventually. His sister is getting married in a couple weeks and I don't want to drag it out, meet his family and everything, and then break up with him right after the wedding.

I really, really care about Tom though and don't want to hurt him. What is the best way to let him know that I care and want to be friends but no longer want to date him?

  • What's the outcome that you really want to achieve? Be friends? Maybe best friends (Like hanging out a lot and so on..)?
    – A.Danzi
    Commented Jul 25, 2018 at 14:18
  • The desired outcome would be for me and him to remain friendly, maybe not close friends (that seems unrealistic) but at least on a talking basis. I don't want him to feel the need to avoid me in public and so on.
    – user19898
    Commented Jul 25, 2018 at 15:02

4 Answers 4


Three musts when ending a relationship:

  1. Make it about your choices, not their faults

For example

Hi Tom. I wanted to give our relationship a chance but I think we should stop seeing each other. I just don't have any strong feelings for you. I'm sorry.

This makes it about how you feel, and what you want. This way, if Tom starts telling you about how you are going to change your mind, or how he can make you like him, you can respond with

Tom, I understand, but this is my decision, not yours. It's not appropriate for you to tell me how I should feel.

  1. Be firm.

Yes, Tom, but I'm sure this is best for me right now. I hope you will understand.

  1. Be final.

I would like to be your friend, Tom, but I don't know how that would work out. I think it would be uncomfortable and I don't want to create false expectations.

If you do plan to date someone else, then you should probably say so explicitly, even though it might hurt. One way or another he might find out, and take it personally -- at least, more so than he inevitably will. I recommend against sugarcoating it.

I'm planning to date other people, and I think you should do the same.

  • 7
    What's the point of saying you'll date other people? Isn't that already implied by the fact that you're breaking up? Usually one mentions seeing other people as a euphemism for breaking up, but you're already saying that more explicitly with "we should stop seeing each other".
    – NotThatGuy
    Commented Jul 24, 2018 at 8:46
  • @NotThatGuy It hopefully stops Tom from no more hoping for "that I'll come around eventually". -- apparently weaker/less explicit statements have failed so far.
    – FooBar
    Commented Jul 24, 2018 at 17:12
  • @NotThatGuy Actually I feel it's for your own peace of mind. Some people may feel irrationally guilty for dating someone new so quickly after dropping someone else -- but if you get it out in the open, you can walk away with a clear conscience. It kind of sucks for the one being broken up with, but frequently openness and honesty sucks less than finding out from "a friend of a friend" or some such.
    – Andrew
    Commented Jul 24, 2018 at 18:48

First and foremost, if you're sure you do not want to date him anymore, you need to end the relationship sooner than later. It will be a lot easier to end the relationship in the earlier, "casual" parts of dating, as usually no long-term commitment has been established. You can initiate the conversation with something along the lines of "Tom, I know we've been dating for a couple of months, and I'm sorry but I don't want to continue dating you." This establishes that there's no second guessing and you've made up your mind (rather than "I think we should see other people"). Even if he tries to assure you that "you'll come around eventually", don't budge on your choice. Initiating break-ups is hard to do, but it's ultimately for the best and will allow both of you to pursue better partners for each of you.

However, staying friends with someone post-breakup is a trickier situation. From what I'm gathering, there is more emotional investment on Tom's side than yours. Therefore, it's hard to tell how Tom will react to the news. While you really care about Tom, you need to accept the circumstance that he may not want to be friends again immediately post-breakup. It's a lot to ask for someone to make such a abrupt emotional pivot like that. Coming from experience where I was dumped by my ex who wanted to remain friends, it took me almost a year to be ready to accept them back into my life. Just give yourselves time to recover and room to grow. I hope this helps, and good luck!


This might not be what you want to hear, but you need to be clear and you need to accept that you will be the "bad guy" in this situation. You feel bad about breaking his heart? Fine. But you already decided you're going to do that (and for good reasons!), so don't try to make your feeling bad about it his problem as well.

I'm not saying don't let him down easy, but telling him you really care about him and you want to stay friends is a cruel thing to do. A lot of people don't seem to realize how manipulative this is (though to be fair, a lot of people probably don't even mean it to be, they just don't think about it and honestly believe they're being nice). Because it's not making it easier on him, it's making it easier on you.

If he's smart and strong-willed, he'll flat out tell you no and take that breakup for what it is. But since feelings are feelings, his thoughts might just go into this direction:

Fine, she broke up with me, but she did tell me she really cares for me... there might still be hope.

It might even go as far as:

As long as I stay friends with her, I will still get chances to change her mind. So it's not a total loss yet.

And then he does stay around you and you're constantly breaking his heart again and again (even if on much smaller scales). Then you start dating and it gets even more difficult for him.

Only he can't even really blame you because you're just friends now after all. Obviously he must have known what he got himself into.

At some point, he might be able to get over you. But you're making it unnecessarily difficult.

It's kind of like saying I don't want to be with you anymore, but I'm happy to torture you for a while.

I'm well aware that some people do manage to stay friends with their exes. As far as my personal experience goes (myself and friends), most of those friendships aren't real (meaning one side still has feelings for the other) and the few that are still had the person who got broken up with go through a tougher time than necessary before they finally moved on.

So if you really care about him: Be tough. Make a clean break and let him move on. Don't string him along in a friendship when you're fully aware he wants more. You can try to befriend him again once he has moved on, though let's be completely honest: That might be never. (It might also be a few weeks after the breakup of course. Who knows?)

But do not try to befriend him while he's still hung up on you. I can't stress this enough. It might soften the blow at first and make you feel less bad about it all, but you're simply preventing him from moving on.

Or to use an analogy a friend of mine once told me: Just because you feel bad about shooting him doesn't mean you should feed him a slow and painful poison instead.

  • Well said. Thanks for pointing this out.
    – V2Blast
    Commented Jul 24, 2018 at 19:44

I'd take the opposite of the upvoted advice - do not make it about you, but about him otherwise you're dumping him and flattering him at the same time. How will he grow from this?

I've been on the receiving end of it's not you, it's me and I intuitively knew it was dishonest and it was unhelpful. That's a double slam: I get dumped and I can't grow from a failure? Can you imagine something worse than not being able to improve? You start this exactly this way, "I could dump you and say it's me and not give you feedback, but I feel that would be mean as you could never grow after this relationship." This is honest and it's much kinder than lying; a lie that prevents growth is awful.

What is it about him that you don't like or that makes you feel you're just friends? Really feel this out. Tell him. If you feel no butterflies, tell him "I never feel butterflies around you. I'm sorry." Whatever makes you feel like he's just a friend, tell him.

The two of you are over, but he can in the least grow after this. He'll learn from this. If you pretend it's all on you and not him, he can't grow. He'll simply feel terrible about being dumped and will feel there's no hope. That's the worst thing you could do to someone. Feedback may temporarily hurt, but that hurt leads to growth. By constrast, no feedback does nothing for the person.

To relate my own example, a girl dumped me and gave me honest feedback about why (unlike the it's not you, it's me girl). It took a year, but I improved from the feedback and I later met an amazing person that I know I would never have been good enough for. I am still good friends with the girl who dumped me because she was honest and I have a ton of respect for her. It took courage, but we're both happier and much healthier as people. That could be you and him; if you truly value his friendship, make sure that he gets a chance to grow as a person from this. You'll be really glad later.

  • 4
    What if there's genuinely nothing wrong with the guy? OP just didn't feel it. Commented Jul 24, 2018 at 15:45
  • Yeah that's my point, he's a great guy I just don't have the same kind of feelings towards him as he does towards me.
    – user19898
    Commented Jul 24, 2018 at 17:58

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