What does it mean to be 'working on yourself'?

Wednesday | July 30, 2025

Love Letters Dating

What does it mean to be ‘working on yourself’?

Have something on your mind about relationships? Send your own letter to [email protected] or, even easier, do it here. Yes, it’s anonymous.

Often in these questions, and occasionally in your answers, there will be a reference to “working on yourself.” I’ve never been sure what that means but I feel like it’s something I should be doing. I recognize there’s no one-size-fits-all answer, but I’d love to understand the idea and how it might apply to me and my dating life.

Some context: I’m in my mid-20s and have been in one relationship in my life. We were long-distance, I was in love and little naive, and she cheated on me. A few years later, she started dating a close friend of mine. So yeah, not a great start. But that drama is peripheral to my day-to-day and on the whole I’m quite happy.

I have close friendships, wonderful family, am starting grad school in a few months and just had my first solo guitar performance after years of practicing. Things are pretty good. And, after a rough spell post breakup, I am once again excited about dating.

But I often find myself wondering what, if anything, I should be doing to “work on myself” in the domain of dating. I’ve never dated much, but am excited about the idea of meeting someone special and building a relationship. But I have the dual specters of my ex (more the idea of having to relive the pain of making myself vulnerable and getting hurt than the person herself) and my own inexperience occasionally haunting my thoughts. These feels like things I should be “working” on, and I worry that I haven’t done enough to become the best version of myself in the romantic realm. From my career to working out to my friendships, I’ve thrown myself into everything but that. So what should I be doing? What the heck is “working on yourself,” both generally and for me?

– Anonymous

For some, “working on yourself” is about learning to have a great time while single.

For others, it’s about finding ways to feel attractive. Many people who write in seem to have a tough time seeing themselves as someone worth dating. Maybe they need hobbies to feel interesting, activity to feel in shape, or new and improved hair.

For you it might be about going to therapy to talk about your ex.

But actually … I think you’ve dealt with a lot of that history. I get the sense you’ve been working on yourself for quite some time without calling it that.

You’ve figured out how to be happy with community, work, and free time – and all of that is how you work on yourself romantically. It means you can start a date as a well-meaning, empathetic, self-confident person.

Now it’s about jumping in and meeting people. You can ask someone out, keep expectations low, and see how it feels. There’s no way to become an expert at this, by the way. You just go forth and and try to make connections.

If you’re asking how to become less scared of vulnerability, lol, let me know if you figure it out. Falling for people is wonderful. It’s also emotionally dicey. That’s life.

But you’ve done the work to know you’ll be OK, no matter what.

Date. Date some more. And if your feelings get hurt, the guitar is for that, too.

– Meredith

Readers? What do you mean when you say you’re working on yourself? Is there a way to work on yourself in dating? Has the work been done here?

Send your own letter to [email protected] or, even easier, do it here. Yes, it’s anonymous.

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Featured Comment

Working on yourself means exactly what it says. You’re working on the things in yourself that you want to improve or change. Or you want to gain some insight or understanding into your behaviors.

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