Movies like My Boss's Daughter

The Break-Up stars Jennifer Aniston and Vince Vaughn in a comedy about a couple who, well, breaks up but continues to live together. Forwarded as a romantic comedy, it presents a relatable tale of love and its complications, much like the awkward situations and entanglements in My Boss's Daughter.

For those who enjoy the underdog protagonist of My Boss's Daughter, She's Out of My League offers a similar vibe. The movie follows an average Joe who meets the perfect woman, whom he believes is out of his league, and it’s his journey of navigating this mismatched romance.

The Hot Chick shares the goofy, over-the-top humor that defines My Boss's Daughter. A body-swap comedy featuring Rob Schneider and Rachel McAdams, it's a laugh-out-loud story that explores identity and empathy in a hilariously unconventional way.

Just Married, starring Ashton Kutcher and Brittany Murphy, is a wild rom-com that fans of My Boss's Daughter will appreciate for its mix of slapstick humor and heartwarming romance. The movie tells the story of a young couple dealing with the mishaps of their disastrous honeymoon, which puts their marriage to the test.

Fool's Gold, starring Matthew McConaughey and Kate Hudson, is a treasure-hunt adventure that has the same comedic tone as My Boss's Daughter. This romantic comedy is packed with action, providing a lively viewing experience for those who fancy a mix of genres.

Guess Who, featuring Ashton Kutcher yet again, puts a comedic twist on meeting the parents. Like My Boss's Daughter, it is filled with awkward situations and cultural clashes that make for a humorous narrative when a boyfriend meets his girlfriend’s family for the first time.

A workplace comedy like My Boss's Daughter, Employee of the Month features Jessica Simpson and Dane Cook in a story about competitors turned lovers. Audiences who enjoy lighthearted tales of workplace shenanigans will find this to be an amusing escape.

Blind Date involves the classic setup of a date gone wrong, which is the central theme of My Boss's Daughter when a man watches over his crush’s pet. This film presents Bruce Willis and Kim Basinger in an equally chaotic romantic escapade filled with unpredictability and wit.