It's Valentine's Day and the Camden's are celebrating the day of love with a special party in honor of the twins first birthday. Eric and Annie fret over how to make the babies birthday a memorable one, while the rest of the family learn different ways of exchanging love on Cupid's Day. After finally gaining her parent's trust, Mary is allowed to spend a romantic dinner with Robbie, only to learn he has ulterior motives. Meanwhile, Simon and Deena confess to their parent's that they've given each other love bites. Also, Matt welcomes his ex-girlfriend Heather back into his life, threatening his relationship with Shana.

Eric and Annie must deal with the emotional fallout as they learn about their kids tumultuous love lives. Mary upsets her parents by announcing that not only has she decided to skip college in the fall, but she is getting back together with Robbie. Matt is forced to choose between his girlfriend Shana (who has moved back to Glenoak for the summer) or his ex-flame Heather, who confesses that she still loves him. Lucy dates Robbie's cute brother Ronald, disappointing Andrew Nayloss who still harbors feelings for her. Also, Simon gets dumped by Deena and Ruthie takes advantage of her new boyfriend.

In the fourth season finale, Simon finds out the real reason why Deena wants to break up with him. Also Ruthie does her best to get back together with her old boyfriend Burt, while Lucy also tries to go after an old flame: Andrew Nayloss. Mary decides to take things slow with her relationship with Robbie and her life. Matt and Shana break up their relationship, but reconciles with Heather. At the end of the show, it shows Matt and Heather may have gotten married- but didn't.