Forty-seven-year-old father and husband, Brad (Ben Stiller), is having a full-blown midlife crisis.
After graduation, he and then-girlfriend Melanie (Jenna Fischer) settled down in Sacramento, "a secondary market," as one of his more successful friends derides.
Melanie works for the government, and Brad runs a one-employee nonprofit, and has for twenty-five years.
In the wake of his only employee quitting ("Because it's so depressing!"), Brad finds himself in Boston, where his and Melanie's eighteen-year-old one and only is interviewing for admission into Harvard's esteemed music program. Their trip together, however, begins with the usual humiliations: Brad's wife purchased a discount fare, so his attempt to upgrade to Business Class "in honor of this special occasion" backfires in a cringeworthy moment of embarrassment, and upon their late arrival to the hotel, Brad and son feast on mini-bar Pringles for dinner.
Over the course of four days, Brad comes face-to-face with his growing sense of inadequacy, inferiority, and doom.
By every measure that matters to him, all his old college buddies are doing better than he is:
Craig Fisher (Michael Sheen) is a former White House staffer and now the best-selling author of Political Beast. Wherever Craig goes, trumpets blare and red carpets unfurl whereupon chatty hostesses wink and give him their best table, personally delivering the finest wines, "Compliments of the chef." Craig's every meal is interrupted by a fan wanting a selfie with the celebrity.
Jason Hatfield (Luke Wilson) runs a successful hedge fund, has four gorgeous children with his wife, and zooms around the world on their private jet eating caviar.
Billy Wearslter (Jemaine Clement) sold his tech company for billions seven years ago, and now frolics on the beach in Maui with two nubile, live-in surfer girls.
Nick Pascale (Mike White) and his partner were just featured in Architectural Digest.
Even Brad's own son is more successful (!), introducing his father to two high school friends who now perform in Harvard's orchestra and have the world by the tail.
Each passing day heaps humiliation upon humiliation, as Brad sinks deeper into despair and daydreams about his friends' latest imagined glories.
On night #2, Troy—Brad's son—falls fast asleep at one of Cambridge's many forgettable economy hotels. Unable to sleep, Brad wanders back to the restaurant where he finds Ananya (Troy's flautist friend) and proceeds to share with her his many life regrets. "Those sound like white privilege, male privilege, First World problems, Mr. Sloan." Her respect for him now downgraded to contempt, he is crestfallen anew. "I'm not a cliché, Ananya; this is my life!" No sympathy to be found, he slinks back to the hotel, now hung over.
On night #3, Brad finally connects in person with Craig, who recalls a series of events in recent years to which Brad was never invited, be they wedding or memorial service. Adding insult to injury, they occurred without his even being remembered. On behalf of his friends, Craig apologizes—sort of, but then proceeds to describe Jason's legal troubles, and his three-year-old daughter with a tethered spine. And then Billy's cocaine, heroin, and alcohol addictions. And then Nick's sexual escapades that have made him persona non grata among East Coast blue bloods. As Craig further bashes their mutual friends, Brad tosses his napkin on the table and makes his way across campus to his son, who is now attending an orchestral performance by the flautist and cellist from last night's dinner.
Their performance is melodic, rapturous, and, "In that moment, I felt life flow through me again," Brad narrates, weeping uncontrollably now.
By the end of their trip together, Troy says to his dad, "Your friends are jerks. Can't you see? Mom and I love you, and we're the only ones whose opinions matter."
As the film climbs to its revelatory conclusion, Brad accepts that he is, indeed, enough. That his career, his life, his life's work is enough. That Sacramento remains a beautiful town, and their home. That he loves Melanie like never before, and she adores him in her peaceful, easy way. That their son—whether here/there/or busking for change as a struggling musician for all we care—is the accomplishment of a lifetime. "This boy that we made together, Mel...he's an amazing human being."
We never learn Troy's academic fate and, of course, it is immaterial by now.
Brad is back, better than ever, eventually embracing the discovery that contentment is not having what you want—or what others seem to have—but is, on the contrary, wanting what you have.
And Brad has it all.
He had it all along.