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Hank è il leader di questo gruppo eterogeneo, un arcigno burocratico del 21esimo secolo che fa di tutto pur di divertirsi. I suoi amici, leali ma poco utili, sono Charlie, un vagabondo incallito che va costantemente sulle tangenziali in cercare di un episodio bizzarro della sua vita, e Sid, un edonista amante del divertimento e con un tocco per il melodrammatico. A complicare le cose ci pensa Margaret, una donna sfacciata e sicura di sé che si fa strada nel gruppo dei tre amici e che si rifiuta di andar via, perchè non ha intenzione di prenderle da nessuno. Ciò che unisce i quattro è la convinzione che non siano ancora finiti. I quattro sono determinati a vivere la terza età e renderla il periodo più bello di sempre. Perchè, alla loro età, cosa hanno davvero da perdere?

Nel giorno del suo 65esimo compleanno, a Margaret non va di festeggiare. Ma Hank, Sid e Charlie insistono per portarla fuori per una serata da "buona vecchia giovane" in un club, ma questo li fa sentire più vecchi che mai.

Margaret e Sid incoraggiano Hank e Charlie ad iscriversi su un sito di appuntamenti online. Ma quando Sid si rende conto che Charlie è triste perché nessuno lo contatta, ha un idea....

Walt Il figlio di Sid, lo sorprende con una visita, Margaret è allo stesso tempo scioccata e divertita nello scoprire che Walt pensa che suo padre sia etero.

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.

Hank and Margaret lose a cornhole competition to some resident cheaters and, as a result, miss out on the coveted prize—a new 65″ flat-screen TV. So, the gang attempts to steal the TV, which means breaking in to Allison’s office after locking her and Sid in the sauna.

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.

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 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 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.

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.

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.

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 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.

As Hank and Margaret mentor an awkward high school student and help him decide on whether or not to go to the prom, Hank is forced to face a traumatic event that happened to him in high school. Meanwhile, Sid's boyfriend invites him to tour the wine country on bicycles, but Sid is mortified because he doesn't know how to ride a bike.

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 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.

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 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.

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.

Hank is excited to give his son the perfect wedding gift in Las Vegas, until he finds out Lorraine's boyfriend, Reggie, is paying for everything. Meanwhile, Margaret and Sid's luck at the blackjack table quickly takes a turn, and Charlie hopes his old Vegas connections will come through for him.

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.