On a date I wonder if there is going to be any sex, and if I'm going to be involved.

In this line Shandling uses self-deprecating candor to puncture the romantic ideal of “a date.” Instead of presenting dating as graceful courtship, he frames it as anxious uncertainty about expectations—especially sexual ones—and his own desirability. The humor comes from saying the quiet, awkward thought out loud: that part of dating is a private negotiation of hope, fear, and ego. It also reflects Shandling’s broader comedic persona—neurotic, self-aware, and willing to expose insecurity as a punchline—turning vulnerability into observational comedy about modern intimacy.