Meet John and Jeffrey, two 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 fall for the same woman. However, and to their astonishment, she decides that she wants to date them both.
When Jeffrey hurts his elbow in a basketball game against two younger players he refuses to let John operate because he's afraid of hospitals. This doesn't sit well with John because he wants a rematch against the younger players.
John doesn't like it when Jeffrey's ex-girlfriend Gina shows up again. He's afraid it will ruin the plans he has for him and Jeffrey.
Hugh reluctantly invites John and Jeffrey to a yacht party with Hugh’s model friends; however John and Jeffrey accidentally board the wrong yacht which is populated with mourners on their way to spread their friends’ ashes at sea.
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 honour of twenty years of service as a judge.
Gina claims to have gone into therapy and changed her behaviour. However, John refuses to believe her, but Jeffrey allows Gina to come along on a spelunking expedition where she falls and breaks her leg.
When Jeffrey and John's neighbor, Brock, 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 John’s ex-wife, Kate announces that she is engaged, John is ecstatic because he won’t be paying alimony to her anymore. Jeffrey suspects that Kate’s fiancé is gay after admitting that he’s ‘living a lie’.
Jeffrey notices that John’s constant bickering with their attractive middle-aged next door neighbour is just thinly-veiled flirtation. Meanwhile, a sexy law student flirts with Jeffrey; however they do not have much in common with each other.
When John’s date accuses him of being unemotional, John pretends to cry, however she sees through him. Meanwhile, Jeffrey cooks in a smoky kitchen because his building manager always ignores his pleas to fix the broken vent and a stuck window.
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.