"So even if this guy is 37, jobless, materialistic and dates many different woman?"
I wouldn't want to date any guy who was jobless and materialistic, regardless of age. Any man trying to get in your pants will seem "nice" of course - are these the qualities you want in a man?
Being sensible in your dating life can save you tons of heartaches, although most people don't have the grit to turn down an attraction that they know is bad. What are your values and do they coincide with his? If he's truly materialistic and jobless, are you the type that wants to take care of someone financially and emotionally? Only you can decide whether to proceed.