What if I’d never broken up with him?

What's been on your mind about your love life? Send your own letter (or update) to [email protected] or fill out this form.


In 2020, I broke up with my boyfriend/best friend because I felt like I wasn't getting what I deserved in a relationship, like basic communication. We also just had different ideas of what we wanted, and my friends didn't like him at all. After several months of processing the breakup in therapy, I've been on and off the typical dating apps. But my problem is that no matter how hard I try, my dating life never goes beyond talking on whatever app I'm using. Half of the time I get straight rejected (which I understand is part of the dating world). The other half of the time, I get ghosted despite my efforts to continue a conversation or meet in person.

Even after deleting all my apps, I struggle to connect with anyone in real life, enough for me to actually feel attraction to them. And even when I do find someone, they don't return the same feelings. All this has led me to feel self doubt about myself.

Sometimes, I feel like I should have just stayed with my ex instead of breaking up with him. He was my first serious boyfriend and we were best friends before we started dating. I feel like he's the only guy who will ever love me. I get that I'm still fairly young and that I don't need to be in a relationship to be happy. But I would like to be in one. All my friends are in serious relationships and I miss the intimacy of having a partner to grow with. And I know that I deserved better in that relationship, but I can't help but wonder what would have happened if I didn't break up with him. Would I have been happy or content with that life? Is it even worth trying to find a relationship anymore?

– Wondering

If you hadn't broken up with him, you would be writing to Love Letters, asking questions about what you deserve and why you're still with a first love who doesn't treat you very well. You would not have slipped into some era of contentment. You ended it because it was time.

Dating is this difficult – sometimes. It's more complicated when a partner is the thing you want most. If that's the case, the rejection, ghosting, and lack of connections feel bigger. If you were happy in a relationship and applying for jobs, it'd be the same thing. The one thing you want feels out of reach.

But it isn't. Because sometimes, just when we think it's never going to happen, it does. Or it doesn't, so we focus on other things ... and then it happens, but when we don't need it as much, so everything feels less intense (in a good way). That's why my advice is to come up with a longer list of things you want. Maybe love is at the top, but under it is seeing new places, finding friends, or learning something you've been curious about. You're in this great place to do whatever you want. Please take advantage.

I wish I could tell you that apps get easier. There are so many people on those things, but the quantity can make the experience overwhelming. If you rejoin, limit your time on them. Maybe 20 minutes of swiping and messaging a night.

Also remember that you were probably coupled while some of your friends were single. There are cycles with this, and maybe one goal can be reaching out to companions who share your place in life. You want to grow with a partner, but you can grow with friends too. Even the coupled ones.

Also, for media, watch "Sliding Doors," please. Whenever friends wonder if they've chosen the right path, I bring out that 1998 movie and they seem to calm down. I'm sure other people have "Did I make the right decision?" viewing ideas for you. Let's make a list.

– Meredith

Readers? Was the breakup a bad idea? How to you push through this kind of dating fatigue and doubt?