Will it ever happen? (I know this is cliche)

There's another one of your problems.

 

1) everyone carries around some baggage, its just not very probable that you have never been hurt by a relationship, its the ups and downs of dating

2) plenty of people want to date someone with low self esteem. low self esteem is not a bad thing, its just means you don't thinks your wonderful and uniquely completely special, just like everyone else.

3) okay, yeah your right on that one. its hard to date someone who is always feeling down. but on the upside, if someone does fall in love with you during a depression chances are that they are in for the long haul!

 

1)Yeah, but deal with your baggage before entering into a new relationship. I dated a guy once that was still trying to resolve issues with his ex girlfriend, and he would talk to ME about it because he said I was the only person he could talk to. I didn't want to hear that bullshit. I doubt many people do. Its not fair to bring your ex into your new relationship. Deal with it before so you don't have to bother a new person with it.

2)No, that means you're humble. Low self esteem is entirely different from just not being full of yourself.

3)true, but it also starts the relationship off on a rather unhealthy foot.

 

I felt the same way at 18. There's muuuuuch more time and MANY more fish in the sea. Be patient and don't act desperate.

 

You need to stop thinking about girls! Focus on yourself, building your confidence, become the sort of man you want to be. Be the sort of person you are proud of, the sort of people you believe is worthy of being loved. Live your life!

Only then will you find someone who deserves you and vice versa. You would be surprised how it falls into place when you aren't obsessing about it. Most of all, believe it will happen when the time is right. Which is not now, but relax and it will!