El padre de Annie, Charles, está visitando a la familia Camden, pero tiene una nueva novia, Ginger. Annie está realmente molesta porque su padre ya está viendo a alguien desde que su madre murió hace solo unos meses. Matt conoce a una chica en el aeropuerto, Heather. Más tarde, le pregunta una cita y se entera de que es sorda. Lucy sigue el consejo de Simon y se tiñe el pelo rubio. Mientras que en el parque, Mary se encuentra con un chico, Wilson y su hermano pequeño SUPERADO, Billy. Van a una cita más tarde esa noche. Al día siguiente en la iglesia, Annie sale corriendo. Mary decide seguir a su madre, pero es atropellada por un auto que corre a toda velocidad cuando la persigue al cruzar la calle.

Mary intenta hacer que Wilson diga que él la "ama", pero Wilson cree que es un gran compromiso y que no se conocen desde hace mucho tiempo para decirse esas palabras. Mientras tanto, Simon y Ruthie leen las cartas de amor de Matt a Heather y las atrapan. Matt los engaña dirigiendo una de las cartas a la "Sra. Matt Camden". Por esto, Eric encuentra accidentalmente la carta que lleva a pensar que Matt y Heather se casaron durante el verano, lo que le preocupa a él, a la madre de Annie y Heather, la Sra. Cain. Por último, Eric ayuda a la amiga de Lucy, Laurie a acercarse más a su madre.

Simon wants to buy the perfect gift for Deena; Lucy's ex-boyfriend is spending time at the Camden's home; Heather is engaged.

The whole Camden family is invited to Matt's deaf ex Heather's wedding to Mason, celebrated by Eric. Matt brings current girlfriend Shana, yet ends up convincing the bride to leave the groom at the altar and drive away together. Wile his ex Lucy flirts with Joe, Jordan gathers the courage to tell her he's dating Mary. Simon is confused after being kissed by Deenah's cahoot.

Matt brings unamused Heather, who hoped he would propose again, back to church, where he exposes after some hesitation groom Mason's flaw, while desperately trying not to lose 'abandoned' Shana. Simon learns the kiss was a 'love test', which is rewarded with more, and Jordan encourages to just enjoy it without excessive worries. Jordan tells Lucy, who out of mere jealousy makes out with wedding guest Joe. Eric has a hard time accepting Julie's sudden announcement to marry Dr. Hank Hastings, but doubts soon shake that couple to be.

Each one of the Camden kids has a relationship problem; Mary decides to skip college and get back together with Robbie; Simon is dumped; Matt is torn.

Eric threatens Robbie with eviction because he thinks he's keeping secrets about Mary. The house is abuzz with secrets and preparations for an elaborate surprise party for Eric's birthday. Johnny drops Mercy on the Camdens' doorstep after Frankie abandons them. Mike trusts Lucy enough to look after his mother for a day, during which the woman surprises her, both by speaking and by what she says.

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.