Movies like The Dilemma

Old School is a raucous comedy that finds humor in the attempt of three men to recapture their glory days by starting a fraternity. Like The Dilemma, it deals with adult men dealing with their personal and professional lives in humorous ways.

Featuring Vince Vaughn as one of the leads, Couples Retreat follows four couples who attend therapy sessions while vacationing on a tropical island, which leads to a humorous and touching examination of love and friendship.

While Horrible Bosses is more focused on the workplace, its comedic tone and the chemistry between the male leads as they deal with their intolerable bosses might resonate with fans of The Dilemma.

The Internship reunites Vince Vaughn and Owen Wilson in a comedy about two salesmen whose careers have been torpedoed by the digital world, leading them to a coveted internship at Google, where they must compete with a group of young, tech-savvy geniuses.

This movie offers a funny yet poignant look at relationships, much like The Dilemma does. The Break-Up, starring Vince Vaughn, who also stars in The Dilemma, navigates the complexities of a couple trying to cohabit while breaking up.

I Love You, Man is a bromantic comedy about the platonic love between two friends, much like The Dilemma centers on the friendship between its male leads. Its blend of humor and the exploration of adult friendships make it a fitting companion piece.

Delivery Man features Vince Vaughn as an affable underachiever who discovers he's fathered 533 children through anonymous donations to a fertility clinic 20 years ago, bringing its own unique blend of humor and heart.

In Four Christmases, Vince Vaughn and Reese Witherspoon play a couple that struggles to visit all four of their divorced parents' homes on Christmas, resulting in a funny yet heartfelt film that explores relationship dynamics.