A night-on-the-town movie for the pre-middle age crowd, The Last Time You Had Fun is out to show that divorce, kids, and growing disillusionment doesn’t mean life can’t still be lively. Mo Perkins’ comedy follows four adults, each in the midst of some sort of relational rut, who meet at a wine bar. Clark (Kyle Bornheimer) is recently divorced and his best friend Will (Demetri Martin) is expecting a baby in his now loveless marriage. Will convinces Clark to celebrate his divorce with a night out. In a stretch limo. Clad in his trusty sweatpants, Clark gives in and he and Will embark for the night. Meanwhile, sisters Ida (Eliza Coupe) and Alison (Mary Elizabeth Ellis) also head out for the evening as Alison, whose 5-year-old has detracted from the spark in her own marriage, attempts to get her sister’s mind off her cheating husband. When the four discover over wine that they have quite a bit in common, they decide they deserve a night of fun. Into the limo they go (driven by Charlyne Yi with her driest of dry humor). As they drive around LA, getting drunk, looking for pot (in a hilarious scene involving Jimmi Simpson as Ida’s philandering husband), and trying to recreate the fun they once had in younger years, they help each other face the realities of their lives.

With four immensely talented leads, the comedic timing and sharply written jokes (Hal Haberman, Perkin’s husband, wrote the script) are spot on. The same sex-jokes, pot humor and sexual tension that abounds in raunchy teen comedies is even funnier when put in the hands of four adults trying to channel that same energy while acutely aware of their age. Balancing humor and introspection well, each character is allowed to come to their own realizations about their situations without feeling overdone or schmaltzy. The film shows a little hypocrisy in the end, juxtaposing the problem of one character, a cheating husband, with the possibility of other characters also engaging in infidelity, as though unhappiness ever justifies that sort of behavior. But the connections the characters form with one another are where the film stays strong.

The Last Time You Had Fun plays to some overused gimmicks: spouses coming out of the closet, children sucking life out of relationships, sexless marriages, serially cheating spouses that can’t just be gotten over. However, their stories and misadventures play out with such great pacing and just enough self-awareness the film can’t help but be thoroughly enjoyable. Misery makes for great company and definite hilarity. Mo Perkins proves herself a director up to the challenge of matching Judd Apatow at his own middle-aged comedy game any day.