John and Jeffrey are complete opposites who can only agree on one thing – they only have twenty good years left to live. In spite of the differences between the two, they vow to live each day as if it were their last – without looking back and without any regrets.
John and Jeffrey go to a rock music club. To their surprise, the club’s sexy owner flirts with them and invites them to an afterparty. The duo end up dating her at the same time and she offers a challenge that may be too much to handle.
When Jeffrey injured his elbow in a basketball game against two youngsters, he refuses to let John operate as he's afraid of hospitals. This doesn't sit well with John because he wants a rematch.
John doesn't like when Jeffrey's ex-girlfriend Gina arrives. He's afraid it will ruin the plans he has for him and Jeffrey.
When Jeffrey and John's neighbor Brock Manley invites them to apply for membership in The Magellan Adventure Club, an exclusive, all-male club, it leads the two friends into an initiation process they didn't bargain for.
As they prepare for Thanksgiving, Jeffrey struggles to teach Hugh how to make the perfect pie and John makes plans to hunt for his turkey dinner. Meanwhile, John finds out about Stella's relationship with the doctor hired to replace him.
When Jeffrey accidentally buys a bong—thinking it is a vase—John sneaks it into the background of a formal photo being taken of Jeffrey to be hung in the courthouse in honor of twenty years of service as a judge.
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When John’s date accuses him of being unemotional, John pretends to cry but she sees through it. Meanwhile, Jeffrey cooks in a smoky kitchen because his building manager always ignores his pleas to fix the broken vent and a stuck window.
When John’s ex-wife Kate announces her new engagement, John is ecstatic because he won’t be paying alimony anymore. However, Jeffrey suspects that Kate’s fiancé is gay after admitting that he’s ‘living a lie’.
Jeffrey finds the woman that he wants to spend the rest of his life with and, as always, John’s not happy about it. Feeling rejected, John goes to Las Vegas and returns the next day with a new wife, a Korean blackjack dealer.
Jeffrey notices that John’s constant bickering with their attractive middle-aged neighbor is just thinly-veiled flirtation. Meanwhile, a sexy law student flirts with Jeffrey; however, they don't have much in common.