Matt tutors silver spoon James Potter in history, refuses to help him cheat but is still in trouble when the professor smells a rat. Simon's new classmate Lee Patterson boasts his cool dad works with FBI and even NASA, but actually is an unemployed ex-con and petty marijuana dealer. Lucy regrets taking a school secretary job, is flattered when older hunk Tyler asks her for a dance, but that bubble bursts when he actually wants the password to enter the school computer.

The next Valentine's day, Robbie prepared a surprise for Joy. Mary meanly supposes the hotel she overheard him contacting by phone means another sex trap. Joy, who assumed the butler to be away like her father really is, isn't discouraged, but bitterly claims Robbie doesn't love her truly because he refuses to risk getting intimate. Matt contacts all his 'true lovers', wondering why he never stayed hooked up. Lucy again assumes Jeremy, who is back in town and double-dating with Mike, wants her back and pretends to have a date. Mary is shocked to see Wilson moved back and goes steady with her former school friend Corey Conway. Simon gets permission to let his hot senior date Maria 'help babysit' and gets her cute kid brother Jake to spare Ruthie dateless embarrassment.