According to some (see here, here, and here), flirting with a male bartender or male patrons results in Larry’s death in the first game of the series. However, lists and videos of all available deaths or ways to fail in the game do not list this as a possibility.
The only confirmed case of flirting with a male character resulting in a “game over” we could find is in Leisure Suit Larry 6. If Larry flirts with Gary the towel attendant, the game ends with the following screen. You can see the full scene in this video (at about 2:30).
LGBTQ references in this game series:
Leisure Suit Larry (1987): Comedian’s jokes
Leisure Suit Larry 3 (1989): Bobbi and Kalalau; Suzi; Cross-dressing; Lesbian Cannibals
Leisure Suit Larry 5 (1991): Sign in airport
Leisure Suit Larry 6 (1993): Gary; Gay Game Over; Cavaricchi; Shablee; Larry’s Reaction to Shablee
Leisure Suit Larry: Magna Cum Laude (2004): Spartacus gay bar, Ione, Luba
Leisure Suit Larry: Box Office Bust (2009): Damone LaCoque
- AgentAnnK. (2008, December 8). Almost Every Death in Leisure Suit Larry 1. YouTube. https://www.youtube.com/watch?v=gxIlm6nEN-0
- Comment section Bears In Games Episode 5 – The State Of Gays In Games Pt2. (n.d.). Retrieved from https://www.youtube.com/all_comments?v=lLrqwOdOAgc
- Fasta Killa. (2001, October 27). Leisure Suit Larry AGI Full Walkthrough. https://www.youtube.com/watch?v=gxIlm6nEN-0
- Leisure Suit Larry. Retrieved from http://gaming.wikia.com/wiki/Leisure_Suit_Larry
- Leisure Suit Larry 1: In The Land of the Lounge Lizards. (n.d.). Retrieved from http://www.abandonwaredos.com/abandonware-game.php?gid=MTI1OA
- Leisure Suit Larry 6: Shape Up or Slip Out! (n.d.). Retrieved from http://en.wikipedia.org/wiki/Leisure_Suit_Larry_6:_Shape_Up_or_Slip_Out!
- Sierra Chest. (2009, December 25). Leisure Suit Larry 6: Ways to die. YouTube. https://www.youtube.com/watch?v=dQ9398qFfRY
- Talk: Leisure Suit Larry in the Land of the Lounge Lizards. (n.d.). Retrieved from http://en.wikipedia.org/wiki/Talk%3ALeisure_Suit_Larry_in_the_Land_of_the_Lounge_Lizards#Death_by_flirting