Men and Money

I love "judge" shows, especially Judge Judy and People's Court.
Many cases feature a woman (both the young and mature) suing an ex-boyfriend, ex-fiance,ex-lover, for a "loan" she made him when they were together.

Now these "loans" vary from a small amount to larger amounts - for a car, or down payment on an apartment or for a computer, etc. These men often claim that the money were "gifts" (she wanted to help me out).

So my question today is:

Would you lend your boyfriend money if he needed it?

Does it matter how long you have been dating or if you were
in a long-term, serious committed relationship?

Does it matter how much money?

Does it matter what the money was for?

I once dated a guy who asked me to loan him money to go on a ski
trip with his boys. The ski trip just happened to be on Valentine's DAY !!
(Was he an idiot? Boy do I know how to pick 'em -lol). The conversation ended with a simple no.

But what are your thoughts on men and money?