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

Spark to a fire

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

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).


Do you have a question for Eli and Josie? Ask it here!


Originally appeared at She Said He Said

Photo: Flickr/Justine-reyes

About She Said He Said

Eli and Josie, friends since college, realized how lucky they were to have one another—an honest friend of the opposite sex who tells it like it is. They wanted to share that with the world and so www.shesaidhesaid.me was born.


  1. Interesting …

    “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.”

    I totally disagree with this. Whenever a guy has shown interest in me then handed over his number instead of asking for mine, it’s always felt like he was copping out and handing over the risk / responsibility to me, instead of taking it himself. It has never worked out well for me at all! Different strokes for different folks, I suppose.

  2. True that! But one caveat: when you get out there, chose things to do that women also like to do.
    My mistake was that I got intensely involved in the two things I love most, cycling and live music, and found that the only girls out doing these things were there with their boyfriends. Music clubs in particular were a real sausage fest unless you already had a date! Never noticed any of this stuff before….

  3. AnonymousDog says:

    All of the advice tendered above, in the article and in the comments kind of assume this guy will have plenty of opportunity to encounter women to date, or men and women to make friends with. He points out in the last sentence that he will be attending a school which relatively few women attend. I think this is a critical factor in who he will encounter socially, and his likelihood of meeting women to date. Having attended a school like that myself, I think the vague general advice that he ‘go out and be social’ will probably not help him as much as the folks offering it hope.
    Saying he has”plenty of time” to gain experience does not take into account the fact that once he gets out of school, he will never have the amount and variety of social opportunities as an ‘adult’ that he will have as a student. I think he deserves to know that.

    • +1

      In my hobbies I meet married women and men mainly, I don’t think I’ve talked to a single woman for quite some time actually. In a small town it can be especially hard since there is little night life, and most activities are catered towards families. Get in whilst you can!

    • FlyingKal says:

      If he is more of an introvert or shy guy with next to no experience, I think it is paramount to tell him to start out and try his wings as soon as possible.
      Especially if he is going to enter a school with less women than men, he is also probably going to enter up in a field of work with the same or even worse (for him) proportions.Being in that environment, the guy is gonig to need every advantage he can get, to get noticed. Only the people you already know will note that you are kind and generous. It will not do much to help you get to know new people.

  4. Dating is a numbers game. You will get rejected a lot even by women who are less attractive than you. The key is to pick yourself up quickly and move on. Don’t be bitter, angry or entitled (much much easier said than done). You have to meet and talk to a large number of women. If you want to lessen the chance of rejection focus only on those you have a real connection with and really enjoy. Even if you do that you will still get rejected but a lot less. Don’t be desperate. Be extremely patient and take your own sweet time. Always be willing to pass on any girl if you don’t like her. The interesting things is this: you can be rejected by a girl you don’t find that appealing and enthusiastically accepted by a girl who is your perfect 10. There is no fairness or logic to any of this. So its in your interest to have some reasonable standards. It will also leave you less bitter. There is nothing worse than being rejected by a girl that you don’t even find that attractive.

    And I agree with the He Said advice…the best way to meet women is through your social circle. Make lots and lots of friends, socialize and have fun. Talk to women whenever you can without any agenda. When you find a women you like try asking her out. Later, rinse, repeat and eventually you will have a girlfriend.

  5. Stephen Webb says:

    Mark Manson, who is a writer for this site periodically, has some fantastic dating advice. It boils down to “make sure you’re interesting and the rest will fall in line”. I also didn’t start dating until I was 18, and I have to say that my first go at a serious relationship was pretty fraught. Part of it was my lack of experience compared to hers, and part of it was just that I didn’t really have a lot of things in my life that MADE me interesting. Check out the dating section at http://www.markmanson.net, I think it’s a reasonable way to get a good start for reading more. But dating is also an activity — you can read about mountain climbing for years without ever climbing a mountain.

    Your first paragraph screams “nervous” or “confused”, which is totally natural. I’m nearly 30 now, and I still feel a little nervous and confused every time I ask someone out. I’ve just gotten a lot better at ignoring my apprehension and keeping in mind that I’m bringing some pretty neat stuff to the table. It’s natural, and as you go out and have more experiences, dating and otherwise, the nervousness will get gobbled up by your confidence.

  6. Dating is such a crucial part of our young adult lives, and we’re rarely taught how to do it well. I think women, especially those with big hearts that you’ll want to attract anyway, will be charmed if you approach them in a modest way. You don’t have to say, “Hi, I have zero experience at dating,” but a variation of a shyly spoken, “this is pretty new to me” will sound endearing if you’re sincere.

    • Christian (New Hampshire, USA) says:

      @Christian Toto: Love the first sentence you typed. You’re absolutely right! Dating is definitely a crucial part of every young man’s life. I’m 34 years old and looking back on life, I have so many regrets. I’ve never gone a date with a woman to a quiet restaurant where I was able to gaze into her eyes over a dimly lit candlelight dinner – I’ve quietly yearned for that for so many years. Instead, when I was 18 years old, a couple of my friends introduced me to porn and ever since it’s porn, porn and more porn. Recently, after doing much research on the Internet (i.e., self-help websites that deal with porn addiction and other self-help websites), I’ve come to the realization that I made a huge and grave mistake by watching porn for all these years. Porn is about escaping discomfort and to suppress negative emotions in your life (i.e., crappy job, no girl, low self-esteem, etc.) and it’s not about being perverted. For some people, alcohol is their crutch or hard drugs……for others, like myself, porn satisfied for a long time – the problem is that I never knew it was bad, nor did I understand why I was engaging in the behavior.

Speak Your Mind