Movies Like Jenna's Tough Love

If you liked Jenna's Tough Love (2005), a movie, 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
A Christmas Kiss II (2014)
★ 5.8/10
At a Christmastime event, Jenna shares an impromptu, unforgettable kiss with the dashing billionaire, Cooper Montgomery. Unaware of his intentions and fearful of getting hurt in another relationship, Jenna vows to…
2
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
3
Splendor (1999)
★ 6.2/10
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
4
Love Me Love Me (2026)
★ 6.1/10
After her brother's death, June moves to Milan for a fresh start, finding comfort in Will, the perfect honor student at her new international school. But when his troubled best friend James—hiding a dangerous life in…
5
Watching the Detectives (2007)
★ 6.3/10
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets…
6
Five Star Christmas (2020)
★ 6.9/10
After moving back to her hometown, Lisa (Lenz) plots with her siblings and grandparents to help her father's bed and breakfast get a five-star review from an incognito travel critic (Webster), but ends up falling for…
7
Christmas in Evergreen: Tidings of Joy (2019)
★ 6.8/10
A skeptical writer shows up in Evergreen to get the scoop on the town's famed passion for Christmas during a search for a long-lost time capsule.
8
Won't Back Down (2012)
★ 6.2/10
Jamie Fitzpatrick and Nona Alberts are two women from opposites sides of the social and economic track, but they have one thing in common: a mission to fix their community's broken school and ensure a bright future for…
9
The Trials of Cate McCall (2013)
★ 6.4/10
In order to be reinstated to the bar and recover custody of her daughter, a hotshot lawyer, now in recovery and on probation, must take on the appeal of a woman wrongfully convicted of murder.
10
Chasing Papi (2003)
★ 6.7/10
Playboy 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…
11
Made of Honor (2008)
★ 6.5/10
Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets…
12
Never Kiss a Man in a Christmas Sweater (2020)
★ 6.5/10
Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.
13
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
14
Love Is in the Air (2023)
★ 6.2/10
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
15
Our Kind of Traitor (2016)
★ 6/10
A young Oxford academic and his attorney girlfriend holiday in Morocco. They bump into a Russian millionaire who owns a peninsula and a diamond watch. He wants a game of tennis. What else he wants propels the lovers on…
16
A Glenbrooke Christmas (2020)
★ 6.5/10
As Christmas nears, heiress Jessica Morgan seizes what seems like her last chance to experience a relaxed Christmas and heads off to the small town of Glenbrooke, where she meets a handsome fireman.
17
My Date with Drew (2005)
★ 5.9/10
Ever since the second grade when he first saw her in E.T. The Extraterrestrial, Brian Herzlinger has had a crush on Drew Barrymore. Now, 20 years later he's decided to try to fulfill his lifelong dream by asking her…
18
Christmas on Windmill Way (2023)
★ 5.9/10
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas…
19
Magazine Dreams (2025)
★ 7/10
Aspiring bodybuilder Killian Maddox struggles to find human connection in an exploration of celebrity and violence. Nothing deters him from his fiercely protected dream of superstardom, not even the doctors who warn…
20
Hands of Stone (2016)
★ 6.6/10
The legendary Roberto Duran and his equally legendary trainer Ray Arcel change each other's lives.