Honestly, it's not the money or the car. If that's all it takes, then the girls you're going to get are shallow and only interested in the material stuff. Sounds like you just need more confidence and a positive self-image. Any women worth pursuing will like you for your inner qualites, your sense of humor, honesty and sincerity. Ask "her" questions, get "her" to talk about "herself". When you make it all about the other person, you improve your chances greatly. She'll find out about you (the important stuff anyway) by the way you talk to her, so there's little sense in bragging about yourself. Make it about her.