Go out with him again. What have you got to lose? The second date might go better than the first one. Too, there's always the possibility that he wanted to get everything out in the open to make sure you wouldn't have a problem with his "wild" past if it came up down the road...kinda backwards, but I know people who do that.
The gambling thing...well, a lot of people gamble, and usually when you gamble you lose.
My aunt ended up broke for
years even after her divorce because she had to pay off gambling debts her lovely husband accrued while they were married, but since you only went out once, I don't think you have to worry about that kind of situation right now. As long as he's got enough $$ to take you out every now and then, it's cool.
