I have no trouble meeting or saying hi to girls... but lose confidence in the dating "process" because am always nitpicking on cost of the date silently.. I am pretty sure they notice this so it makes me not want to date... but am in my early 30s and really need to get the ball rolling!

So I live in the nyc area... VERY high cost of living. I work here and work does not pay enough to really afford a vivid social life. And dont say quit and find something else.. I did that before and I spent 6 months "interviewing" and playing the resume game, only to get turned away.

So I am sick of having to constantly worry about money... and having it get in the way of relationships. It has caused a few disputes with a few girls last year that may have otherwise become my serious girlfriend.

I am trying to start a web biz soon to make more money... and in my other post I asked advice on which one would you folks start if you had the choice?

I am debating whether to launch a travel website where I make money on commission whenever I sell a luxury travel package.... OR a website hosting business, where I make a steady monthly fee each month, for selling web hosting plans to small business. They can both be run from home in my spare time, as I must continue to keep my dayjob in the travel industry... which is most of my experience.

I am really eager to hear your advice!!!! My parents give 0 advice on anything. My old man simply does not have the empathy or understanding.
So I must turn to online forums. and yes this is obviously a psych issue. In 3 years I have launched 4 FAILED web startups, making 0 money, and not sure how to make it work this time.

WHAT WOULD YOU DO??? help!!