Portrayed by Shailene Woodley, Amy gets pregnant by student Ricky Underwood after a one-night stand at band camp before her freshman year of high school.
Ben proposes to Amy after finding out, because he genuinely loves her, and feels he would be a better father than Ricky due to his family's financial stability.
After breaking up with Ben during her sophomore year, Amy briefly dates Jimmy, the son of her mother's ex-boyfriend, but their relationship ends after he finds a condom in her purse.
The summer before Ricky's sophomore year, he impregnated Amy Juergens after a one-night stand at band camp, finding out about her pregnancy a few months later.
When Amy's mother Anne, tells her that she must support her baby on her own, she changed her mind and decides to marry Ben, as his family is financially stable.
Both George and Anne say no to the idea, so she ends up running away with the help of her grandmother Mimsy, who gives her ten thousand dollars.
Their relationship ends again when a security camera catches Ricky saving Grace from two men after Jack left her in a bad part of town.
Jack is in critical condition after a pimp beat him with a baseball bat in his dorm room for paying an underage prostitute without sex and helping her escape.
Grace and Jack share a kiss the next morning after the party, which is captured on a cell phone by Daniel's ex-girlfriend, Raven.
After George realizes Anne really is gay and he has no more feelings for her, he starts to date his first wife Kathleen (Grace and Tom's mother) again.
She dated an architect for a while, and they planned to marry when she became pregnant, thinking it was his child; he later confessed that he could not have children, and she realized that Robbie was George's son.
She and George made an attempt to get back together and she took over the design portion of his furniture business, but again she finds poorly-hidden evidence that he was unfaithful, and resumed divorce proceedings.
Alice Hirson portrays Mimsy, Anne's mother, Amy, Ashley and Robie's grandmother and John Juergens great-grandmother.
In season 5, Ashley takes advantage of her Alzheimer's and convinces Mimsy to give her $10,000 to run away to Italy for cooking school.
She becomes a widow after Marshall dies in a private jet crash and began dating a younger man named Dr. Jeff Tseguay, a gynecologist, much to Grace's displeasure.
Kathleen tries to balance supervising Tom's special needs with his desire to be independent, and tries to get Grace to behave responsibly when it comes to sex.
Jack moves into the main house when Tom begins dating a woman with two children that he met on the bus on his way to work as a Vice President of Human Resources.
They resume their relationship, and while Madison is seriously considering having sex with Jack, she confesses that she isn't quite ready, wanting the occasion to be special and wearing a pretty dress and having her make-up done.
After school ends, Madison sleeps over at the Bowman guest house (where Jack stays) and lies about where she spent the night.
Jeff later joins a medical team working for an extended period in Africa, where Grace visits him and meets Daniel.
Jeff invites Kathleen to join him in Africa for a few months, and although tempted, she doesn't feel that she can leave Tom and Grace.
In one of the last episodes of the season her mother dies and while awaiting a flight on her soon-to-be ex-husband's private jet she is approached by a divorce lawyer.
Bryan Callen portrays Robert "Bob" Underwood, Ricky's biological father who has been to jail for drugs and child molestation.
Later, Margaret and Sanjay have dinner with Anne and George to discuss Ricky's custody case, and expressing a desire to be a part of John's life.
Margaret decides to take in one of Ricky's former foster brothers, Ethan, who ends up in juvenile detention after sexting nude pictures of an underage girl to his friends when she breaks up with him.
After a minor case of cold feet, Cindy and Ruben decide to marry the day before Leo and Betty's wedding in a judge's office.
After offered a job at his alma mater in Phoenix, Arizona as the head of the Philosophy department, he gives up the church and moves with his wife, leaving Jack to complete his senior year.
He and Grace stay abstinent through their summer at Med Camp, and have sex after school starts when Grant's parents are out of town.
Their relationship hits a speed bump in the road after Ethan makes a disastrous first impression to the prospective parents, who later tell Kathy to break-up with him.
Played by Michael Grant, Ethan is Ricky's 14-year-old foster brother who ran away from their house a few years after stealing a knife from Margaret and Shaker.