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Dear Caitlin No. 6: No one has ever asked me out. Am I not dateable?

Updated: Sep 7, 2022

Dear Caitlin,

I am 23. I have never had a real boyfriend. I have never been asked on a date. I am not sexually active. My DMs are dry. As I know looks are just a small portion, I am a very beautiful young lady. I am very well educated, and I have a nice personality to accompany me. I refuse to settle, as I have learned from the mistakes of my friends and family. But I often attract guys who do not seek a real relationship with me? I am even in therapy healing parts of myself. Is something wrong with me? Why am I not dateable? How can I attract better men? How do I go about getting into a good relationship?



Dear Anonymous No. 6,

First of all, I don’t make promises lightly, but I can promise you that NOTHING IS WRONG WITH YOU. You’re completely worthy of the love you want. If you’re struggling to find someone, you’re somehow getting in your own way, and you haven’t yet figured out how you’re doing that. When you figure that out, you’ll be able to get out of your own way, and create the relationship you want.

It’s imperative that you continue working to heal from old wounds. It’s also imperative that you find the right guidance to show you what you’re doing to get in the way of finding someone. Some helpers are better at being able to point out ways you’re being self-protective, for example, that aren’t working for you, or ways you’re not being boundaried enough, etc. It takes finding someone who is specialized in helping people struggling the way you are, and not all helping professionals specialize in dating & relationships.

It sounds like a big part of your struggle is that you’re waiting for men to come to you. You mentioned that no one has ever asked you out. There could be 1 million reasons for that to be the case, but none of those reasons matter. What matters is what's in YOUR control. You can't make people ask you out, but you can ask THEM out. I’ve found that when people wait to be asked out, they could wait forever.

Plus, even someone who, for example, gets a lot of messages online & gets asked out a lot, is not necessarily going to find the RIGHT person….just lots of people. And that can be exhausting. You have to go for who you want. Often that means overcoming the fears that come with that, such as fear of rejection and not being enough.

You mention that you attract men who don't seek a real relationship with you. So, again, don't wait for men to come to you and hope one is emotionally available. Go for who you want. Spend a few minutes on an online dating site--I recommend actual sites, not apps--and look around for someone you think is interesting. Contact them. This part is a bit of a numbers game, and eventually you'll hear back from someone. Just don't give up. You never know who is on and no longer using their account, so if you don't hear back, there could be a lot of reasons for it. Avoid making up stories about why you’re not hearing back, and just keep trying. This was one of the ways I took control of my own dating journey. I met my husband by reaching out to him because his profile interested me.

Until I started choosing men who were actually ready for and interested in a relationship, I found the same exact type of men as you’re describing--the ones who weren't emotionally available and didn’t want a relationship with me. And to be honest, looking back, I really dodged a lot of bullets. No one feels dateable when they choose men who don't want a relationship. And when you choose the same type of man again and again, you start to question what's wrong with you. But remember this, it's not YOU, it's who you're choosing. If you choose someone who is ready for a relationship, you'll have way better luck. If you continue to meet emotionally unavailable men, you’ll continue to feel undateable.




Need advice on dating, relationships, self-worth, boundaries, break-ups, or mental health? Send your questions anonymously and Caitlin will answer in an upcoming Dear Caitlin column! Fill out the application below!

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