Good romance movie where the man will do anything to date the woman

In Your Eyes (2014) or The Big Steal (1990) might scratch that itch.

Might be a little more left-field than you are looking for but I love the movie Birthday Girl

https://moviechat.org/tt0188453/Birthday-Girl

It's kind of a romance and Ben Chaplin's character kind of does the most outrageous things for love (or for the hope of it).

Nicole Kidman plays a very convincing Russian mail order bride too.

Almost no one has seen this movie but it's really good and won't give you a toothache like most sickly sweet romcoms. Definitely black comedy though, so be warned!

How To Lose a Guy in 10 Days (2003) a little different to what you might be wanting but it is hilarious and fits the idea of a guy who just sticks with the torture in the hopes of winning.

Natural born killers?

Gun Crazy

Beauty and the Beast!

Fear (1996)

Berlin Syndrome (2017)

Pepé Le Pew.