This. R3d, pay close attention to what Shodan is saying about dating being a ‘numbers game’.
Statistically, the large majority of women aren’t going to be interested in the average man (this is less true the other way around, I think), so if you ask out a particular girl that you’re interested in, most likely she’s going to say no. That’s not (necessarily) a problem with you, and certainly not with her, it’s just the luck of the draw. You need to get used to being turned down, and able to get up, dust yourself off, go along your way and be ready to ask out someone else. And you need not to respond to rejection by becoming self-hating and unhappy. The more you’re ready to hear a ‘no’ with equanimity, the more likely you are to start hearing a ‘yes’.
Some of the other advice given here is really good too. You need to start thinking about what you can bring to a relationship (serious or casual), and working on self-improvement, in some way or another. Too many people, I think, focus on what they want out of a relationship, rather than what they can bring TO the relationship. Working out is a good idea, so are getting involved with things like volunteer work, outdoor activities, etc… Broaden your range of interests, and be ready to talk to a girl about her interests and feelings, not just your own. And yes, you should work on trying to get better at just starting conversations with people you meet, even in situations where you have no romantic interest. Once you become better at casual conversations, that’s a step closer to becoming better at having serious/intimate conversations.

