Seymore Butts Interactive II: In Pursuit Of Pleasure (1994)

Seymore Butts Interactive II is the sequel to the original Seymore Butts game, with a similar play style. This time, Seymore is trying to hang out with his girlfriend Brianna, who has left for Canada. In order to follow her there, Seymore needs to earn some money by starting some kind of voyeuristic dating service - he hooks up his friends with girls in the Los Angeles area and he (you) watch the dates and decide what the men should do to win the women.