Going through a first breakup (and it is terrible)

Friday | March 6, 2026

Love Letters Breakups 🖤

Going through a first breakup (and it is terrible)

This letter is a great bookend to a letter from earlier this week.

I’m a guy, just turned 25, and it’s been seven months since I got broken up with in what was my first real relationship (lasted only about two months), but I haven’t been able to stop thinking about her.

I have people telling me that I miss being in a relationship more than the actual person I dated, but when I try to think of anything I didn’t like about her, I’m grasping at straws. I fell for her so hard and she somehow checked off every single one of my boxes, so now I’ve managed to convince myself I’ll never find someone as good as her again (I didn’t even meet her on the apps, but I’d been trying to date for a while. One compatible person after about five years is not a great ratio).

For additional context, she said she was breaking up with me not because of anything majorly specific that I did, but just that she stopped being into me and that we were too similar. There were no warning signs and everything appeared to be going well. We had plans to get together that night and she even said it was something she had decided shortly before coming over.

She’d been having a tough year and made it sound like it just wasn’t the right time and she also seemed disappointed, like she really wanted it to work out, which only hurt more to hear. I believed in that moment that I shouldn’t have had to say anything to convince her to stay – if she liked me enough, we wouldn’t be having this conversation in the first place – but I still find myself replaying some of those moments asking myself why I didn’t fight harder for someone I cared so much about. Maybe I just didn’t want to make things any more difficult for her.

I’ve asked ChatGPT for advice, watched videos, and have talked to many of my friends and family (my dad at least made a hilarious joke about how I’d have more time to focus on our joint fantasy football team. Happy to report we won the championship!), but I can’t seem to figure out how to get over her and move on.

I’m also aware that trying to contact her would most likely be a mistake, even though I really want to (I encourage anyone who disagrees with that sentiment to let me know so you can fuel my delusion). Where’s that memory eraser device from “Men in Black”…? But in all seriousness, how do I move past this?

– Broken Up

Your “Men in Black” is my “Eternal Sunshine of the Spotless Mind.”

That movie teaches us (no spoilers) that we should not forget our difficult memories because they’re part of the process. If you’ve never seen that one, please do.

Also watch “Sliding Doors,” one of my favorite breakup movies ever. You can pretend you’re Gwyneth Paltrow running through the city, figuring out what you’re supposed to do about your romantic life when it all goes wrong. I find that film deeply soothing.

There are many good movies about awful breakups because it’s a universal feeling. That awfulness you’re experiencing is so …. human.

Congrats on being a person who feels things deeply. What a great trait – especially when the happiness arrives.

As you grieve, consider that the people in your life might be right. If you date a woman for two months, you might know the great stuff about her, but not what makes you incompatible. It could be why you think you’ve lost a perfect person – because she bailed before you could learn more.

Your gut is right – do not reach out. It’s possible she said all those things about timing because she thought it would be a nicer way to say goodbye.

The apps are tough, but they’re worth continuing. There are some wonderful people on those platforms who are going through breakups too.

This was a first girlfriend. A first love, perhaps. Maybe she’ll always seem like the one who got away.

But she chose to go away. There’s nothing you could have done to make her stay, and you’re right, you shouldn’t have to beg. Certainly not after two months.

– Meredith

Readers? Advice on getting through a first breakup?

Is there something on your mind about a relationship in your life? Or a relationship you wish you had in your life? Send your own question. Help others wondering the same thing. Use the form – or email [email protected].

Breakups 🖤

Featured Comment

You will grow from this experience if you allow yourself some grace. Now’s the time to circle your wagons and build yourself up: get in great shape, work on your career, perhaps make a big move or take an epic trip. When you’re ready, get back out there and date with an open mind and heart.

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