It's Valentine's Day in Newport, and everyone is preparing for the Valentine's singles benefit. Luke has a new crush, while Sandy gives Seth some sex advice. An old friend of Ryan's shows up in town, which forces Marissa to lay her feelings on the table. Seth and Summer take their relationship to another level.

After Caleb is released from custody, he must make some decisions about the Newport Group, and his decisions don't sit well with Kirsten. Seth is determined to win back Summer's friendship, even if it means getting a job. Ryan has a string of awkward encounters with a new girl at school, while Marissa faces being alone.