7) Shoshanna and the Doorman – Season 2, Episode 8
When Shoshanna leaves a party early, she runs into the building’s doorman on her way out and tells him, “You’re, like, really good looking for a doorman.” Despite Shoshanna being in a relationship with Ray, the two start to hook up in the building’s mail room. At the time though, Shoshanna’s biggest concern (which she interrupts their make out session to ask) is “What happens if you leave the door?” to which the doorman replies, “A tranny walked in last time, and he was just walking on the floors, but it was nothing, I swear to god.” Her worry resolved, Shoshanna and the doorman continue their hookup.
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