Movies Like My Lady Boss
If you liked My Lady Boss (2013), a comedy and romance movie directed by Jade Castro, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.
- 1
Little Italy (2018)
★ 6.6/10Also comedy and romanceFormer childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
- 2
Relationship Goals (2026)
★ 6.4/10Also romance and comedyWhen TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her…
- 3
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedyThando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
- 4
Set It Up (2018)
★ 6.9/10Also romance and comedyTwo overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
- 5
Easy Virtue (2008)
★ 6.5/10Also comedy and romanceA young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
- 6
The Other End of the Line (2007)
★ 6.5/10Also comedy and romanceAn employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
- 7
Good Advice (2001)
★ 5.9/10Also comedy and romanceAn investment banker loses everything and must discover what's really important in life.
- 8
Only the Lonely (1991)
★ 6.2/10Also comedy and romanceDanny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the…
- 9
Chasing Papi (2003)
★ 6.7/10Also comedy and romancePlayboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored…
- 10
Love, Weddings & Other Disasters (2020)
★ 6/10Also romance and comedyA fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
- 11
Boot Camp (2024)
★ 6.1/10Also romance and comedyUnathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
- 12
The Wrong Paris (2025)
★ 6.7/10Also romance and comedyDawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
- 13
Can We Still Be Friends? (2017)
★ 6.1/10Also comedy and romanceDigs a no fuss, no frills kind of guy and idealistic achiever Sam who are friends turned lovers turned exes. Their relationship as a couple lasted for almost eight years until they both decided on an amicable breakup.
- 14
Hollywood Stargirl (2022)
★ 6.6/10Also comedy and romanceWhen Stargirl's mother is hired as the costume designer on a movie, they relocate to L.A., where Stargirl quickly becomes involved with an eclectic assortment of characters.
- 15
The Kissing Booth 2 (2020)
★ 7.6/10Also comedy and romanceWith college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.
- 16
Keeping the Faith (2000)
★ 6.1/10Also comedy and romanceBest friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now…
- 17
Speechless (1994)
★ 6/10Also romance and comedyIn the midst of election season in New Mexico, political speechwriters Julia Mann and Kevin Vallick begin a romance, unaware they are working for candidates on opposite sides.
- 18
5 to 7 (2014)
★ 7.1/10Also comedy and romanceA young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.
- 19
Your Christmas or Mine? (2022)
★ 6.4/10Also comedy and romanceStudents Hayley and James are young and in love. After saying goodbye for Christmas at a London train station, they both make the same mad split-second decision to swap trains and surprise each other. Passing each…
- 20
What Women Want (2000)
★ 6.4/10Also comedy and romanceAdvertising executive Nick Marshall is as cocky as they come, but what happens to a chauvinistic guy when he can suddenly hear what women are thinking? Nick gets passed over for a promotion, but after an accident…