Puck! (Drama Special) - to payback his wife's debt, ML ends up working for the loan shark as a gang member & debt collector - you know the type you always see in kdramas that use threats & violence to collect their money
Others that are not exact of what you're asking for:
Drama Special Season 7: My Happy Home
Liar Game - 'Liar Game" is a sketchy, underground swindler type of game where participants are each given 100 million yen, and the aim of the game is to trick other opponents out of their hundred million yen. If you win, you keep the money, but if you lose you go hundred million yen into debt. FL is anonymously picked & forced into such game where she has no choice but to participate. When she loses the game she contacts ML, who's one of the best swindlers in town, to help her win it back to pay back the debt.
There are 2 seasons + a movie; I've only seen the first season. There's also a Korean version which is slightly modified. I don't remember the plot details, but I think the FL was also used as bait to lure ML to participate in the game.
Meloholic - you can kind of say that his life took a turn because of a woman. There are 2 women. Fist one is the ex: had he not been at her place at the wrong time, he would had never obtained his special abilities. The second woman is his future girlfriend: because of her and her list of admirers he gets entangled with some stalkers.