Tomcats (2001)

A group of friends decides to make a bet among themselves, the one who marries last will receive an impressive amount collected from each. It seemed to each of the guys that he would be able to resist the temptation to become the husband of a charming beauty and remain a bachelor until old age, but in fact everything turned out to be completely different. Almost all the guys got into women's networks and became respectable husbands, only two managed to escape the marriage shackles and live a bachelor life, but which of them will win the bet, the big question is?

Michael Delaney works as a cartoonist, he draws well, but despite his talent, he manages to live in debt, which he will soon need to repay. He decides to marry the second bachelor in order to collect his winnings, and makes an insidious plan in which he tries to make a friend fall in love with an attractive policewoman. But events turn around so that Michael himself falls in love with Natalie, and Kyle refuses to enter into a serious relationship.