Mary, still intent on her independence, finds herself buried under a number of unpaid bills after losing her job at the pool hall. Meanwhile, "The Colonel" (guest-star Peter Graves) surprises Eric and Annie with an unexpected visit. Matt blames everyone but himself for his failing grade in organic chemistry class. Lucy enlists Simon to assist her with her Homecoming Queen Campaign to help him gain popularity in school, and Ruthie's prayers are answered when she's transferred out of her nemesis' class and into a prestigious private school.

The episode was rated 7.63 from 32 votes.

Tensions run high as a doubtful Julie lets Mary baby-sit Erica, only if Mary has no visitors. But when Frankie (guest-star Chyler Leigh) comes by and begs Mary to take care of her baby Mercy, Mary can't resist helping her. Then, Mary is then caught with an open bottle of beer while babysitting. Meanwhile, Lucy volunteers to chaperone Ruthie's sleep over and to watch the twins. Also, Simon is on a quest to change his image and does this by piercing his ear. Matt pursues a woman who wants nothing to do with him. Also, Eric and Annie clash with Mary's disreputable friends.

The episode was rated 7.67 from 21 votes.

Still unemployed and bills mounting, Mary continues her downward spiral to rock bottom as Eric and Annie fight about how to effectively deal with her numerous lies and immature behavior. Meanwhile, the fear of what may happen to Mary starts to take toll on the rest of the whole family. By this, it is prompting the children to break open the twins piggy banks to help Mary pay her bills. To get the credit card company to stop calling, however, they are forced to make a risky decision. During all this, Mary CONTINUES to ignore her responsibilities.

The episode was rated 7.76 from 21 votes.

Exasperation reaches an all-time high in the Camden household, as Eric and Annie helplessly watch their oldest daughter Mary and her worrisome friends continue to head down the path of destruction and into the hands of the law. When Frankie (guest-star Chyler Leigh) expresses interest in signing up for college classes Mary starts checking out Lucy's early application packets. Meanwhile, Simon has a hot date and Lucy gets a weird proposition from a classmate. Lastly, Ruthie discovers manipulative fun of keeping a diary--- much to the embarrassment of Eric and Annie when she sees them having SEX!

The episode was rated 7.77 from 22 votes.

The striking resemblance of Robbie's new friend, Marie, to Mary raises eyebrows among discerning Camdens. Annie's invitation for her to stay for dinner makes things weirder for them. Back in Buffalo, unbeknownst to Robbie, Mary accidently bumps into her old boyfriend Wilson (guest-star Andrew Keegan) and his son Billy at the train station and makes plans to meet him for the evening. Mary is unsure on whether she should tell Robbie, but confides in her family about this. They all say that she should tell Robbie about this, but decides to ignore their advice. Also, Matt meets Robbie's ex-girlfriend, Cheryl, at the restaurant where she works. He starts to have feelings for Cheryl and tries his best to try to get her to go on a date with him. His efforts work by the end, but is having a hard time telling Robbie about his interest in his ex-girlfriend.

The episode was rated 7.82 from 22 votes.

The Glenoak Community is making a big fuss over a petition that is protesting the apparently unfair firing of one of Ruthie's teachers, Mrs. Miller at her private school. Although, Matt knows the real reason of why she is leaving since she has been to his hospital after being diagnosed with advanced breast cancer, which leads to the embarrassment of many of the petitioners--- including Simon and Lucy when they encounter her brother who's a teacher at their high school. Also, Annie's father Charles drops by at the Camden's for a visit. Annie is then surprised and shocked when her father passes on news to Eric--- to tell her that she has a sister, Lily.

The episode was rated 7.86 from 22 votes.

After their lackluster attempt at kissing, Mike (guest-star Jeremy Lelliot) and Lucy agree to be friends and to fix each other up on dates--- but the plan bothers Lucy more than she anticipated. Meanwhile, Matt's in a huff over John and Robbie's newfound friendship and feels slighted by the family. Eric also continues to feel alienated from his family when they keep going to Annie for advice. Also, Annie feels slighted when Ruthie plays an un-funny joke when the twins recognize her as their "mama".

The episode was rated 7.90 from 20 votes.

Mary returns home back to Glenoak for the summer to spend some time with her family, but fears about being together again with Robbie, who's a bit on edge. Meanwhile, Eric and Annie are recipients of what may or may not be advances from unmarried acquaintances (Serena & James). Simon also has his problems with his ex-girlfriend Deena when they both see that the still have feelings for each other, even though she has another boyfriend and has to choose. Also, Matt agonizes over telling his family about his new relationship with Cheryl, but soon decides to tell them all. John and Priscilla are also having trouble again with an unfortunate obstacle with her parents, but they decide to come to their senses and allow the two kids to have their wedding with their help. Lastly, Lucy surprises herself and others when making a proposal to Jeremy and the possibility of going to college in New York with Jeremy. Although plans change when Mary allegedly tells Robbie and soon the rest of the family

The episode was rated 7.92 from 25 votes.

There is cause for alarm when the Camden's disapprove of Simon's new group of friends, one of whom insults Annie and Lucy with his chauvinistic remarks. Norton, the kid that Simon befriends is a fan of violent rap whose negative attitude towards women seems to be influenced by misogynist lyrics. At the same time, Eric and Annie confront Simon about his newfound interest in rap music and somewhat misogynist attitude towards women. Heather gets back in touch with Matt, but Matt is unsure of her intentions. He then finds out that she is dating someone else AGAIN!

The episode was rated 7.93 from 28 votes.

Annie discovers that the particularly flirtatious mother of one of Lucy's friends, Serena is seeing Eric for therapy sessions. Annie strongly requests that he refers her to someone else. Annie then has to deal with the guilt over her jealousy-induced interference between the two. Also, Simon is mortified when word gets around school over the fact that he's a virgin. Annie had shared the details of Simon's sexual inexperience with his ex-girlfriend's (Sasha) mother, Rita. Meanwhile, Matt struggles about telling Robbie he's interested with his ex-girlfriend, Cheryl. Lastly, Robbie is also hiding a secret from Matt that involves his ex-girlfriend Heather.

The episode was rated 7.95 from 22 votes.

Eric and Annie desperately try to figure out how Mary managed to pay her credit card bill while the kids team up to throw them off the scent. When the parents vs. children game finally breaks down, drastic changes happen. After learning that Mary stole from the twins to pay her bills, Eric and Annie come to the heart-breaking realization that they must take drastic action to help their misguided daughter and to protect and preserve the family. The Camden's gather to confront Mary with their feelings of hurt and betrayal and their conclusion to send her away to Buffalo with "The Colonel" and Grandma Ruth.

The episode was rated 7.95 from 22 votes.

As Annie plans a mysterious day of cleaning as Eric discovers the shocking news that Mary ran away from "The Colonel"'s to come back home because of a devious scheme she had with Robbie and freaks out. Eric is convinced that more trouble is brewing and goes to insane lengths to find answers. In reality, Mary is heading home for a huge surprise birthday party for Eric, attended by all the people whose lives he's changed for the better in the past few years. Chores at home are interrupted, however, when Ruthie discovers Frankie and Johnny's baby, Mercy at the Camden front doorstep. Meanwhile, Lucy stays with her friend Mike's (guest-star Jeremy Lelliot) near catatonic mother for the day, and drops a proverbial bomb on Lucy. Also, Matt and Simon try to figure out why they delivered Mrs. Bink (guest-star Eileen Brennan) to the hospital.

The episode was rated 8.00 from 27 votes.

Although Robbie is just as nervous as everyone else, his presence in the house during Mary's weekend stay causes a great deal of concern among the Camden's. Matt and Lucy are especially suspicious after Lucy accidently finds a condom in a misplaced wallet. Imagine their surprise when they learn that the provocative prophylactic belongs to Simon--- who just so happens to be spending the evening with his new lady friend, Sasha.

The episode was rated 8.22 from 23 votes.

In the fifth season finale, Mary tries to right a wrong by explaining to Lucy that she never had "adult relations" with her sister's fiance, Jeremy. The only problem left is trying to convince Lucy. Also, Wilson unexpectedly drops by the Camden home from New York to see if he and Mary are really over by finding out her answer. Also, James talks to Eric about him attempting to have an affair with Annie, as Serena comes clean with Annie about her trying to have an affair with Eric. Meanwhile, Robbie and Wilson set aside their differences so that they can talk about Mary. Lastly, Matt learns a few things when it comes to Cheryl's honesty when she doesn't tell her friends that she's dating him.

The episode was rated 8.27 from 22 votes.

Despite the disapproval from the rest of the family and his own hesitations, Eric takes in Mary's ex-boyfriend Robbie Palmer (Adam LaVorgna) to live with the Camden's for the night after learning that he's homeless. Matt also shows up unexpectedly after being kicked out of his apartment by John, who needs quality time with his girlfriend. Meanwhile, Mary calls home again and hears Robbie's voice on the other end and assumes he's dating Lucy now. Also, John proposes to his girlfriend Priscilla in front of Matt.

The episode was rated 8.45 from 20 votes.