Movies Like Sincerely, Harold Washington

If you liked Sincerely, Harold Washington (1989), a movie directed by Simon Howard, 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
The Perfect Date (2019)
★ 6.4/10
No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.
2
Hard Luck (1921)
★ 6.9/10
A down on his luck young man makes several attempts at committing suicide but fails them too. He then finds himself becoming more confident through a series of petty adventures, to such an extent that this becomes his…
3
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
4
Casanova (2005)
★ 6.5/10
With a reputation for seducing members of the opposite sex, regardless of their marital status, a notorious womanizer discovers a beauty who seems impervious to his charms. However, as he continues to pursue the…
5
In the Blood (2014)
★ 5.8/10
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
6
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…
7
Endless Love (2014)
★ 6.9/10
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
8
Succubus (2024)
★ 8.3/10
A new father going through a marital separation joins a dating app and matches with a beautiful but mysterious young woman... whose powers of seduction and manipulation entangle him in a mystery more horrifying than he…
9
Gia (1998)
★ 7.1/10
Gia Carangi meteorically rises to modeling fame in the late 1970s but becomes overconsumed by persistent loneliness and drug addiction.
10
Let's Make Love (1960)
★ 6.4/10
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
11
The Art of Getting By (2011)
★ 6.6/10
George, a lonely and fatalistic teen who's made it all the way to his senior year without ever having done a real day of work, is befriended by Sally, a popular but complicated girl who recognizes in him a kindred…
12
Breathe (2017)
★ 7.4/10
Based on the true story of Robin, a handsome, brilliant and adventurous man whose life takes a dramatic turn when polio leaves him paralyzed.
13
Seriously Single (2020)
★ 6.8/10
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
14
Section 8 (2022)
★ 6.1/10
After avenging the murder of his family, a former soldier is sprung from prison and recruited by a shadowy government agency.
15
House of D (2004)
★ 6.3/10
In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression…
16
The Object of My Affection (1998)
★ 5.8/10
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
17
Tall Girl (2019)
★ 6.3/10
Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi finally decides to find the…
18
Much Ado About Nothing (1993)
★ 6.9/10
In this Shakespearean farce, Hero and her groom-to-be, Claudio, team up with Claudio's commanding officer, Don Pedro, the week before their wedding to hatch a matchmaking scheme. Their targets are sharp-witted duo…
19
Red, White & Royal Blue (2023)
★ 7.9/10
After an altercation between Alex, the president's son, and Britain's Prince Henry at a royal event becomes tabloid fodder, their long-running feud now threatens to drive a wedge in U.S./British relations. When the…
20
I Still Believe (2020)
★ 7.6/10
The true-life story of Christian music star Jeremy Camp and his journey of love and loss that looks to prove there is always hope.