Preferably used with a wing and with a game-show host/party host attitude. "I need your honest opinion on something...do I look gay?" Some chicks will bust out laughing when you ask this. "...Because something really funny just happened, this dude was hitting on me in another bar!"
Better is to use this with a wing and change it to "Does MY FRIEND look gay" because it eliminates the self-conscious aspect. The person who was supposedly hit on must play it off as something totally funny and even flattering.