As Penny (Casey Wilson) tries to delay breaking up with her boyfriend until after Valentine’s Day, Dave (Zachary Knighton) worries that his girlfriend is pulling the same trick on him. Brad (Damon Wayans, Jr.) struggles to complete his Valentine’s Day plans with Jane (Eliza Coupe) after a dentist appointment leaves him high on laughing gas, while Max (Adam Pally) reconnects with an old boyfriend.