Making trouble for a womaniser

[BraveSirRobin]

Diseases.

Magical diseases which the party needs to adventure for in order to find a cure.

 

[Ourph]

Are you playing 4e? The new 4e disease rules are pretty harsh... IYKWIMAITYD.

 

[Lizard]

Pregnancy is good. Wrecked my swashbuckler's love life....

Or you can follow the Xander option -- make sure every woman who he ends up with is a doppelganger/demon/dragon/etc.

There's also the woman who isn't just a simple barmaid/innocent naif; she might decide that he's the one for her, and not be easily dismissed/left behind. Women of power scorned can be terrible foes indeed -- either directly, in the form of a powerful wizard/fighter/whatever, or via politics and wealth. That Human Commoner might have the money to send assassins out -- or just bounty hunters to bring back her One True Love, whether he thinks he is or not.

The nastiest trick, of course, is to have his character finally fall truly in love...and then be tossed aside once she's bored with him, as he's done to so many others.

 

[Tewligan]

"Are there any hot girls there? I wanna do them!"

 

[Stoat]

Pregnancy is good. Wrecked my swashbuckler's love life....

Agreed. I have exactly the same kind of player in my game. After a while, he knocked up a barmaid. There were two beneficial effects.

1) He stopped tomcatting around everywhere.

2) His son grew up and eventually became a replacement PC.

 

[WayneLigon]

The Badger Game - This is an old con game where the woman seduces a man into her bed. In the middle of The Act, the 'husband' comes in and threatens to kill the man, but will accept a considerable amount of cash in exchange for sparing the man's life. Unlikely to work on most PCs.

The Crying Game - 'nuff said.

Spoiler

Or, in case you've never seen the movie, Our Hero becomes obsessed with a pretty young thing only to find out she is a he. Works best with elves.

The Magic Trap - The Act activates a curse placed on the poor woman, turning her into a ravenous beast or gargoyle.

Fatal Attraction - His most recent conquest becomes murderously attached to him, and will seek to kill any other rivals that stand between her and her man's total devotion. First she'll kill any other woman he even so much as looks at, then start in on his friend because they make him take time away from her.

 

[Halivar]

One word: scoopies.

We had a player that contracted it (much the same situation as your player), and he never womanized in-character again.

 

[Terwox]

He even treats them with respect. (save for the leaving them part)

egads.

 

[Krensky]

It depends on your world, but there's always the divine...

A goddess who's portfolio include women or love (or her followers) could get annoyed with him. If said goddess also important for healing or whatnot it could be doubly troublesome.

Or maybe a goddess of love becomes interested in him in a positive fashion. This could also be done as a variant of the angry husband of she's married or involved with a god of war or such.

 

[Remus Lupin]

Vengence Demon.