I Want to Start Dating, But I Don’t Know How

A guy who’s never been been kissed asks Eli and Josie how to start asking women out on dates.  

Originally appeared at She Said He Said

Dear Sexes: I am a guy – 18 years old. I have a problem. I haven't dated a girl in my life before. Not that I need to, because I am not popular. However, that's not my concern. 

I am ready to start dating, but I have no idea where to start. I've never even kissed a girl before, though girls have told me many times that I'm handsome, cute, and stuff like that. Now I'm out of high school, and going to another school with very few girls. Where do I start?

She Said: From a woman's perspective, and having been 18 years old once, I would say the place to start is with women you like, but aren't really your closest friends. Be honest, but don't lay your feelings out completely (after all, until you've explored your romance together, you don't even really know your feelings!).

When you meet or get to know a woman you like, a simple, "Hey, it'd be cool to have a coffee with you sometime. Here's my number” will go a long way. And yes, give her your number. The best of all my relationships were with guys who gave me their number instead of asking for mine. They may not have realized it at the time, but to me it felt like they were putting the ball in my court. It felt empowering, and I never had to worry about someone calling me too much or making me uncomfortable if I wasn’t interested.

It also gives the air of confidence. A "take it or leave it” sort of thing. Like, "Hey, if you want to meet up, that'd be cool. Just give me a call.”

Just don't have business cards printed up for yourself. That's a terrible move.

As far as what to do, just treat the woman as a friend you really value. Start simply – a drink or a coffee. If it's going well, you can always walk to dinner somewhere or see a movie.

Don't plan a big event, just somewhere you can hang out and talk. Keep it short and just be yourself. If you're nervous, you can even say that. Just only say it once!

Dating is like any other skill. Picking up a guitar or kicking a ball felt weird the first time you did them, but with practice you get better and better.

He Said: When you say you're ready to start dating, what does dating look like to you? Do you want one serious girlfriend? Do you want to be monogamous in a relationship? Are you just looking to date around, and have several experiences (to learn more about what you're looking for)? You're just starting your dating, so I'd imagine you're looking to gain experience, but only you know exactly what type of dating you're interested in.

Regardless, if you're ready, you're ready. So don't worry about your lack of experience. Don't focus on what you lack. Think about what you bring to the table, and work on establishing a connection with a girl you like. The best way to increase your chances for success (for now) is to start making more friends. 

I understand you don't want to get caught in the friend zone, but the more people you know, the more you can connect, the greater possibility you can find someone you want to date. Even if you just make a bunch of new friends, those friends will have friends you may like. Friends of friends is often a good dating avenue to explore (just don't let yourself be set-up, and be on your best behavior).

So go out, be social, and be yourself. You have plenty of time to gain experience. No need to rush yourself, just put yourself in positions to increase your social net. You'll make friends, you'll make connections, you'll find some girls to date.

P.S. – Please use common sense and caution if talking to strangers (in person or on the internet).

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