Gabe plans a picturesque date on a sailboat, but it quickly goes awry. While working her first job at a carnival, Amy gets asked out by a corny manager. Fresh out of being un-engaged, Victoria's date goes from romantic to creepy very quickly.

Glenn strikes gold when a gorgeous man asks him on a gym date, but it deteriorates quickly as the man has serious rage issues. Hannah is charmed by a classmate's powerful performance. Jesse agrees to meet a guy from a dating app that is into kink.

Laura offers to walk a man's dog and uses the opportunity to snoop through his house. Jordan goes out with a love interest, and he blacks out from heavy drinking, leaving him to put the pieces back together of what happened the night before.