There's no one way to know, but there are a lot of important things to have nailed down in your life first. I don't claim to have all the answers, because I am still young. But I do know enough to know I don't know much, which is a start. However, here are some gems that I've picked up along the way.
1) Girls will not make your problems go away. If you say to yourself, "Everything would be perfect If I just had a girlfriend" go back to the drawing board. A new girl will make you feel great for a short period of time, but if you are depressed/antisocial/etc without a girl, you will still be that way after you have a girl. Don't get me wrong, it's great to have someone in your life, but you cannot look to someone else to make everything better.
2) If you don't love yourself, don't expect someone else to love you. If even you can't live with you, how can you expect someone else to love you? Ask yourself if you are the kind of person you would like to hang out with. If the answer is no, do something about it. Chance are, if you don't want to hang out with people like you, chances are other people think the same thing.
3) If you want to make someone your girlfriend without even getting to know them, you definitely aren't ready to have one. It's totally fine to be attracted to someone you know, to want to get to know them better, or to want to date them. However, if you want to jump into a committed relationship with someone you don't even know, you aren't interested in the person, you're interested in the idea of a relationship. Tons of people jump from relationship to relationship not because they keep meeting such great people, but because they feel like they need to be in a relationship.
4) Sort of an extension of 3 and 2. If you are pining to be in a relationship, thats one of the surest signs you aren't ready for one. That's the quickest way to end up with the first girl that comes your way and has nothing to do with who they are. In my experience, relationships have been a tricky creature. Whenever I thought I wanted one, I could never achieve it, or I changed my mind. It was only when it was the furthest thing from my mind that all the sudden it entered my life.
In short, don't fret over not having a girlfriend. Most high school relationships don't even count anyway. That being said, don't be afraid to date. It's a great time in your life to get ahead on the dating learning curve, but is totally OK, even natural, to date someone without it progressing any further. Take care of yourself, pursue things that interest you, develop and grow on your own. All these things will make you emerge as a person so much more than defining yourself through a girlfriend. I promise if you that at your age if you just learn to be a cool social guy and not to worry about girls, that entire area of your life will take care of itself.
P.S. I am NOT saying that you should ignore girls. It's great to work on your dating skills so you aren't stuck at a Sophomore level. All I'm saying is you don't have to worry about ticking off that checklist sheet. You know, the one that says; First kiss: Check. Go on a date: Check. Girlfriend: Check, Lose virginity: . Etc Just enjoy the process for what it is. all that stuff will come in due time.
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