Remember Leisure Suit Larry? The aim of the game was to get the pixellated hero laid in an old school Monkey Island style adventure. The security/ age restraint was cool- it asked you general knowledge questions of various vintages to ascertain how much you knew and thus how old you were.
Now there’s Singles: Flirt Up Your Life, a similar premise, but with improved graphics and less linear Sim-ish gameplay.
[EDIT] LLL’s coming back this year as well, with Leisure Suit Larry: Magna Cum Laude