Hank, Charlie and Sid prepare their Friend-iversary party, and don't include Margaret. Noticing the tension between Hank and Sid, Margaret encourages Sid to speak up for himself. Meanwhile, Sid has his sights set on the patio for their party and attempts to convince the cat ladies to release it to them.
In an attempt to date a guy way out of her league, Margaret pretends to be someone she's not. When Hank doesn't hear back from his doctor about a questionable mole, he's convinced his days are numbered, so Charlie helps him get his test results. Meanwhile, Sid avoids John, who has a very important question to ask him.
Margaret helps Sid finally meet his teen idol, Kip Samgood. Meanwhile, Charlie ditches Hank to hang out with his girlfriend, Kathleen, so Hank goes to great lengths to get Charlie's attention.
Sid's new boyfriend feels uncomfortable with Sid's close relationship with his ex-wife when she comes down to visit Shady Meadows; Margaret, Charlie and Hank get ready to have a celebration to behold at an upcoming concert.
Margaret attempts to date the hottest guy in Shady Meadows, but can't seem to rid herself of clingy Leonard. Meanwhile, Hank tries to sell his erotic vampire novel, with the help of Sid's cousin.
While Sid is housesitting a fellow resident's gorgeous high-rise apartment, the Cool Kids get a taste of the good life - and a taste of Charlie's incredible cookies. But when Margaret decides to turn Charlie's creative cookie-making into a new business venture, everyone gets a bit carried away.
Margaret neglects the guys when her best friend, Joanie, comes to visit. When Joanie decides to move in to Shady Meadows, the guys devise a plan to convince her not to, but Hank gets distracted.
The gang rallies around Sid to help him through his commitment issues to new beau John. Meanwhile, Margaret attempts to conquer her fear of flying by volunteering at the airport.
Margaret's daughter, MJ, turns up at Shady Meadows jobless, homeless and looking to be rescued. Meanwhile, Sid attempts to find his wok in Charlie's "hoarder paradise" of an apartment.
Hank signs up to host a Shady Meadows closed-circuit TV show but is quickly replaced by Sid, who dishes out hot retirement home gossip on-air; Margaret helps Charlie woo a widow at her bereavement support group.
When Hank finds out his ex-wife will be at a mutual friend's funeral, Margaret volunteers to lie about his success to impress her; Charlie and Sid crash the funeral against Hank's orders.
Margaret begins dating Karl, a fellow Shady Meadows resident who may or may not be the Zodiac Killer. Meanwhile, the guys are hunting for a different kind of criminal: a serial non-flusher.
When Hank starts dating a much younger woman, the gang suspects she may be a gold-digger taking advantage of him because of his age. But after rifling through her things, they fear this relationship could be something much worse - a pregnancy trap
Margaret scores an invite to an exclusive foodie potluck for Thanksgiving and takes Sid as her plus one, leaving Hank and Charlie to find a backup plan.
Tired of "Gorgeous George" and his reign as activities coordinator, Hank backs Charlie and Margaret backs Sid for the position in the upcoming election, and it instantly turns dirty.
Margaret tries to convince Sid to come out to his visiting son; Hank stubbornly refuses to admit he needs glasses; Charlie tries to help him cheat on an eye test.
Charlie and Hank create online dating profiles, and to boost their egos, Sid pretends to be an interested woman. Of course, the plan goes awry.