I never gamble online, except poker with no deposit bonusses. I have no intention to cash out those, I just prefer ‘free real money’ over play money as this will give you slightly better opponents.
When playing poker with friends (now that I live in the campus dorm of the university this happens about 3 times a week), I always put in real money to make the game realistic. BUT only 1 euro or so, I’ve seen some people here coming from “Ok if I really have to put in money, only the 1 euro minimum” to “come on, let’s go to the casino with 100 euro!” in only 2 weeks.
Tonight I go to the horse racing here in Hong Kong and this weekend I plan a trip to the lovely Macau.