‘Not dating has always made me feel inadequate’

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Dear Meredith,

I am a 23-year-old college graduate who has never been in a relationship. I struggled with mental health issues and making friends in high school and college, but found my way to friendships and health. Now I feel stuck with dating.

I had major crushes on two guys in college and one on someone I met at work. With all of them, things didn't work out and they were either gay or not interested. Some guys have expressed interest either directly or indirectly and I haven't been interested in them. I feel like I've been unlucky, and I'm fairly late to the game – and not dating has always made me feel inadequate. I feel strongly that I want to meet someone in person and not online, but understand that ultimately online dating is something I'm going to have to try given my desire to connect with someone and the reality that I haven't been lucky yet. Any practical advice?

– Frustrated Late Bloomer


Online dating isn't for everyone. We've learned from other letter writers that it can make a person feel overwhelmed, exhausted, and more than a little bit confused. That said, there's something to be said for quantity. When you're swiping on an app, everything feels a little less "major." You can have small wins (a match or short conversation) without feeling like it's all or nothing.

I understand why you see these apps as a last resort, but it's important that you ditch that attitude. The process might be a little bit fun. Think about signing up in the presence of a friend so it feels more social.

Also, please know that even though you feel like a late bloomer, it's not helpful to give yourself that label – especially to strangers. Some 23-year-olds have had significant relationships, but many haven't. Those who've been coupled might be insecure about how little time they've spent being single. Really, we're all inexperienced at something. It's kind of comforting when you think about it.

– Meredith

Readers? Dating tips? Thoughts on meeting people in real life vs. apps? (Made me think of this October letter.)