Tokimeki Memorial - Forever with You
Available on: Playstation
The dating sim genre is incredibly popular in Japan but has yet to find a mainstream audience on this side of the Pacific. Still, that hasn't stopped tons of otaku (Japanese for dork) from importing these turn-based romantic adventures so they can live out the Asian high school affairs they never had.
Tokimeki Memorial - Forever with You is a fairly typical example of your average dating sim. Your goal is to win the heart of as many classmate cuties as you can before graduation day. You'll train at school clubs to improve your stats and skills, make dates, and navigate your way through various dialogue trees to convince the girls that you're the one their heart desires.
Why you can't be caught playing this:
Your Japanese schoolgirl fetish will have your partner thinking you're some kind of child molester if she finds you scheduling dates on your virtual calendar with a bunch of high school students. You can try to explain how you just wanted to learn the Japanese language with a more interactive medium. But when "love hotel" is all you can come up with when asked for evidence of your progress, you might want to look into the many sequels to Tokimeki, seeing as how she'll never go out with you again.
Leisure Suit Larry: Magna Cum Laude (PC, PS2, Xbox)
The Leisure Suit Larry games never showed anything worse than what airs on Cinemax late at night until the original Larry's nephew came along in Leisure Suit Larry: Magna Cum Laude and peed in the punchbowl. Instead of settling for the usual sexual innuendo and heaping piles of corny dirty jokes the series was previously known for, this latest title features full nudity and all out sex scenes. There's really no explanation for your save game right before the big wet t-shirt contest event at Larry's college so do yourself a favor and delete dirty Larry from your hard drive and memory before it's too late.