I have the hardest time breaking up with someone. When I was younger, I used to start being a crappy boyfriend just so that they would break up with me and feel like they did it instead of getting dumped. In my 20’s I did a lot of the it’s not you, it’s me stuff even if it really was them. I’m not asking for a specific relationship right now. I just suck at this and could use advice.

I’m going to answer this with the idea that the relationships you’re talking about are short- or medium-term ones. If you’re in a long-term relationship (longer than a year, or living together, or married), it should look different.

Breaking up is rough in the moment, for sure. I have a very vivid memory of throwing a tantrum that three-year-olds would envy when I realized I had to end things with someone. I just didn’t want to do it, for many reasons.

• How awkward it can be (especially if the person doesn’t see it coming).
• The desire to not hurt the feelings of someone that I generally like.
• Fear of conflict.

I just wanted it to have happened already.

If the relationship isn’t working for you and you don’t see a realistic scenario where that will change, be honest that you don’t see a future for the two of you. It will suck. You’ll be uncomfortable, and they’ll possibly be sad or angry (though they might be relieved). That’s not how most people want to spend a Saturday afternoon, but there isn’t a shortcut. It’s just a thing that has to happen and that will be shitty for a bit.

They may start asking you for a reason, for that one thing that they could just change to keep the relationship alive. I know I have. But as I’ve grown older and experienced a few different relationships, I’ve recognized that when we realize someone isn’t right for us, it’s usually for myriad reasons. It’s partly a chemistry thing, partly a values thing, and partly a personality thing. Something isn’t a good fit.

In hind sight, as memory fades and certain actions stand out, we might say “she was lazy” or “he didn’t like my family.” And while those likely were factors in the break-up, if we were really interested in building or maintaining a relationship with the person, we’d at least try to work it out.

Even if they are asking for a reason, unless it’s a thing that you are 100% sure that they could change and you would take them back in a heartbeat (and you’ve not it mentioned before), or it’s something so vile (they’re racist; they’re violent) that you think they need to know how it affected your relationship*, I don’t see the value in sharing it.

If Joe not being interested in meeting your family is something that made you rethink your relationship, you should share that while you’re still interested in being together so that you can work through it. It shouldn’t be a surprise. Otherwise, it’s just an excuse you’re telling yourself (and them) to avoid admitting that sometimes relationships just don’t work out.

However, if it is something that you’ve shared is a concern for you, and you’ve asked them to work on, and they just haven’t, I think it’s fine to share that. They’ve decided that the thing you want changed isn’t something they’re interested in working on. That’s their call; you don’t have to stick around through it.

It’s not fun. But as someone who has been on the receiving end of the crappy boyfriend move, I can confirm that it’s the shittier thing to do. It’s not cool or respectful, and its definitely a sign of immaturity. You end up stretching things out, and you put the responsibility on the other party. If you know that things are not working out for you, you owe it to the person you’re with, as well as yourself, to end things honestly and as soon as reasonable.

*Those are volatile accusations, so I suggest only sharing them if you’re in a safe, public place and don’t need to be alone with them again.