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.

Annie quits her job at the private school without discussing it with Eric first and he feels completely left out. Mary tries to call Wilson and learns from his landlord that he has moved out of his apartment. Simon uses Robbie's car to practice driving and gets him in trouble when Simon smashes into Matt's car. Robbie's brother Ronald stops by at the Camden home for a visit. Mary gets an unexpected visit from Ben, the fireman she kissed. Ruthie's old teacher Ms. Riddle starts working at Ruthie's school.