Movies Like Love is Always Losing

If you liked Love is Always Losing, a movie directed by Michael D'Alessandro Lena, 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
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…
2
Dinner in America (2022)
★ 7.8/10
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
3
The Crush (1993)
★ 6.7/10
A precocious and obsessive teenager develops a crush on a naive writer with harrowing consequences.
4
After (2019)
★ 7.1/10
Tessa Young is a dedicated student, dutiful daughter and loyal girlfriend to her high school sweetheart. Entering her first semester of college, Tessa's guarded world opens up when she meets Hardin Scott, a mysterious…
5
Marked Men: Rule + Shaw (2025)
★ 6.7/10
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see…
6
Sidelined: The QB and Me (2025)
★ 6.4/10
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving…
7
Memoirs of an Invisible Man (1992)
★ 5.9/10
After a freak accident, an invisible yuppie runs for his life from a treacherous CIA official while trying to cope with his new life.
8
Jobs (2013)
★ 6.1/10
The story of Steve Jobs' ascension from college dropout into one of the most revered creative entrepreneurs of the 20th century.
9
After Ever Happy (2022)
★ 6.8/10
As a shocking truth about a couple's families emerges, the two lovers discover they are not so different from each other. Tessa is no longer the sweet, simple, good girl she was when she met Hardin — any more than he…
10
Springsteen: Deliver Me from Nowhere (2025)
★ 6.6/10
Bruce Springsteen, a young musician on the cusp of global superstardom, struggles to reconcile the pressures of success with the ghosts of his past.
11
Fast Girls (2012)
★ 6/10
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
12
Hider in the House (1989)
★ 6.2/10
A deranged man hides in the attic of a new house and becomes obsessed with the unsuspecting family that moves in.
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
One Chance (2013)
★ 6.7/10
This film follows the remarkable and inspirational true story of Paul Potts, a shy, bullied shop assistant by day and an amateur opera singer by night.
15
Magazine Dreams (2025)
★ 7.1/10
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…
16
The Kissing Booth (2018)
★ 7.2/10
When teenager Elle's first kiss leads to a forbidden romance with the hottest boy in high school, she risks her relationship with her best friend.
17
Thinner (1996)
★ 5.9/10
An obese lawyer finds himself growing "Thinner" when an old Romani man places a hex on him. Now the lawyer must call upon his friends in organized crime to help him persuade the old man to lift the curse. Time is…
18
The Girl in the Book (2015)
★ 5.8/10
The story of a young writer's transformation when her past invades her present.
19
Antitrust (2001)
★ 6/10
A computer programmer's dream job at a hot Portland-based firm turns nightmarish when he discovers his boss has a secret and ruthless means of dispatching anti-trust problems.
20
Taking Care of Business (1990)
★ 6.3/10
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.