At 29, I feel undateable

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I’ve been single since my first boyfriend (of two months) broke up with me over MySpace in 2008. I was a teenager and I was devastated. I sought validation on dating sites in high school, despite being too young. I also sought out boys and men on Omegle. I had never been the object of anyone’s desire prior to my first boyfriend. I was unhappy with my body nearly my whole life and was not confident, but boys/men on those sites made me feel desired.

After those phases, I graduated to dating apps in 2012/2013, when those became more popular. I tried nearly every app and/or website that I could. Nothing ever progressed to a relationship. I was stuck with men that just wanted to hook up or didn’t want to go on more than a few dates with me. To complicate things further, I am technically a virgin, although I don’t love classifying myself as such. I was raised in a Christian home. My parents and the church instilled an importance on not having sex before marriage. I still consider myself a Christian, but have not been to church in many years. I don’t want to wait until marriage to have sex, but I also don’t want to have meaningless sex with someone who doesn’t love me. I feel like this has been a huge hurdle in my dating life.

Who wants to be with the 29-year-old virgin who lacks self-confidence who has never been in a serious relationship? I’ve become so jaded and frustrated with app dating that I recently deleted them all. I have no idea what I should do now. I’m a hopeless romantic that dreams of getting married to the love of my life… if I could just find him.


I’m glad you deleted the apps for now. So much of your dating experience has been online. It’s time to see what it feels like to meet people in the real world, even if that means less quantity all at once.

Apps are designed for quick decisions and ruling people out based on one or two details. But if you’re meeting friends (or others) while doing an activity, you’re bonding over that thing. It’s not about approval or rejection, it’s about the stuff you have in common.

Depending on where you live, there might be Meetup groups or classes to take. There might be book clubs to join. Focus on connections, not love. One often comes after you’re good at the other.

You ask who wants a 29-year-old virgin who lacks self-confidence, and I’ll tell you that I get a lot of letters from people who doubt themselves based on dating and sexual experience. That means a lot of people are where you are – thinking they’re not enough, sometimes for reasons you'd never anticipate. Assume that everyone comes to the table with some insecurity.

Also consider that if you don't need to be married before you have sex, you could try intimacy with someone who likes you a lot. It doesn’t take forever-love to make physical connection meaningful. There are many steps between anonymous one-nighter and “let’s have the most spiritual sex because we’ll be together for eternity.” Some of that middle ground is quite lovely and based on mutual respect.

For now, though, connect to more people in the real world. You can use the online world to find out what’s happening around you in real life. Do one new thing a week. The weather's getting good.

– Meredith

Readers? Pep talk/ideas for this letter writer?