I’m 31 with no dating (or kissing) experience

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Hi Meredith,

I am a 31-year-old woman who has absolutely zero experience when it comes to dating, sex, flings, kissing, hookups. I've never been on a date, let alone held someone's hands before. Ninety-eight percent of my friends are female, and that's always been the case since I was in grade school. I would describe myself as an introvert, a little shy, but I'm personable and can easily hold a conversation with a stranger. In a grocery store, the only people that would come up to talk to me are the elderly. It's endearing, really, but also quite sad. At this point, I feel embarrassed. I don't know what is wrong with me. Granted I am not going out and about making opportunities for myself to meet others at a bar or a club because my introvert self would die at the idea of that. Even pre-COVID I preferred to be at home or, at best, go out for brunch with my closest friends. But I can't help but think, "Is there something wrong with me?" And yes, that is my self confidence speaking.

As I am writing this letter, a little part of me feels like I know the answer to my question, and it's my lack of self-confidence. It's the voice inside my head that sometimes tells me I look wrong, I'm not interesting, or that I'm gross, that prevents me from putting myself out there. I guess my question comes down to: how does someone like me, a 31-year-old introvert with zero experience who lacks self-confidence, start dating? Where do I start? How do I start?

– Helpless


"In a grocery store, the only people that would come up to talk to me are the elderly."

OK, people need to stop perpetuating this myth that it is common to get picked up in grocery stores. I don't think it happens much. People are there for food. Tampons. Halo Top ice cream. Dish soap. Especially in narrow aisles, they're trying to get out of the way.

"Even pre-COVID I preferred to be at home or, at best, go out for brunch with my closest friends."

That’s great! And you're not doing it wrong. I don't know many people who found love at brunch either.

The confidence issue is a real thing, but please know we all have insecurities. It's part of being human. And you're in luck, because so many people who have a ton of dating experience are feeling very out of practice because of a year of isolation. Even if they dated all the time before 2020, they're now having new conversations, concerns about issues they might never have considered, and a great deal of patience. I think it's a good time to get out there because a lot of people are learning together.

"Where do I start? How do I start?"

Tell your friends you're ready for set-ups. Get on some apps (have a friend on the couch next to you, if that’s safe) and try to start up simple conversations with any matches. If you don't want to meet up with people, that's OK. If you want to start with a FaceTime, that's OK too. If the conversation is stilted and awkward, that's not you, it's just life. Move on to the next. Normalize small talk that leads to more.

Lean on the fact that everybody's a little rusty right now. You have great friends and can talk to strangers. That’s half of it, really.

I know the kissing (etc.) part is scary, but please remember that any time a person kisses someone new, it's a first kiss. They learn things all over again, and the experience feels different than it did with the last person. They might have done more kissing with others, but they’ve never kissed you. They'll be doing something for the first time too.

– Meredith

Readers? Is it a good time to start dating? What advice do you have for someone who feels lacking in experience? Self-confidence? How are you dating right now?