Every woman has had the misfortune of dating a guy who thinks he’s too funny to be an asshole. Jay is that guy.

After a date gone wrong, Jay tries everything in his power to make Eileen laugh, but nothing seems to work. In a last ditch effort, he gives Eileen a gift. What seems to be a successful romantic gesture is interrupted by Will, a heavyset homeless man who just wants a subway swipe to see his daughter. Prideful and not wanting to lose his positive momentum, Jay makes fun of Will to try and get a few laughs out of Eileen but only makes the situation more tense and awkward.

The duo leave Will stranded behind the turnstiles, trying to put the embarrassing situation behind them. Unbeknownst to them, Will manages to find a way to get past the gates.

With nobody around and the next train 10 minutes away, Jay finds himself trapped with Will and stuck with two choices: to bite his pride or commit to the bit.