I like my friend but he is really insecure

thats a toughy. I've had to deal with bfs whove been the same way. the only thing you can do is hope that over time and the more time he spends with you the better he will get. his insecurity can't just be fixed over a day or even a couple months its going to take a long time and a lot of effort on your part. another part of being insecure is having a low self esteem, so make sure you do things like reminding him how cute he is and giving him compliments all the time to boost it.

Every guys last girlfriend messes them up "big time". Don't give him any slack for that. There are some guys with less money, looks etc who are great and wonderful guys and then there are guys who know deep down that you are a better person then they are. I mean better in the sense of good heart, personality, got something going for yourself in your life - potential.

I once dated a guy who thought I was too good for him - for 2 1/2 years I dated him. Turns out - I was too good for him. I overlooked issues about money, lying, his insane family, his bad temper, everything. I had a million read flags - yet, I just wanted to be the one "there for him". Raise his self confidence, give him what he didn't get before and the list goes on and on. I wasted 2 1/2 years. I saw the light after that he had told me upfront.

The guy will give you indications prior to the relationship on if he thinks it will work out - whether he knows it or not. I think this is one. You can try it out but be careful. Please don't waste 2 1/2 years of you rlife. If those red flags start waving - run. Best of luck to you!