Voadam
Legend
If you want to have a Gambling Womanizer, in most editions of D&D, you go for a Rogue. In 4th, you can do so much easier, though it may cost some feats to make a skill trainable.
That's not my experience at all. I played a 2e character who womanized and gambled, he was an elven transmuter. He went to casinos, played cards, and hit on women.
Being a rogue instead of a wizard would have been no help at all in basic, 1e, or 2e unless you convinced the DM that cheating at cards is a pick pocket roll instead of dex. Womanizing was not a thief skill. Its not until 3e that you have any class based mechanics for success at womanizing. Previously if the DM wanted to incorporate mechanics for such things (and not all did) he generally called for a charisma check.
I prefer to generally not have mechanics for non-combat/powers character concept things and just leave them to roleplaying and ad hoc DM adjudication.