Movies Like Do's and Don'ts of Dating

If you liked Do's and Don'ts of Dating (2018), a movie directed by Jonathan Milton, 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
Think Like a Man (2012)
★ 6.8/10
The balance of power in four couples’ relationships is upset when the women start using the advice in Steve Harvey’s book, Act Like A Lady, Think Like A Man, to get more of what they want from their men. When the men…
2
The Wrong Paris (2025)
★ 6.7/10
Dawn 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.
3
The Matchmaker's Playbook (2018)
★ 7.1/10
After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But…
4
Two Can Play That Game (2001)
★ 6.5/10
Corporate overachiever and all-around fly chick Shanté Smith thinks she's got the goods to keep her slickster boyfriend Keith, from straying—until he discovers a greener pasture, Shanté's archrival, Conny. Scorned, she…
5
What's Your Number? (2011)
★ 6.5/10
Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96…
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
How to Be Single (2016)
★ 6.3/10
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions…
8
How to Lose a Guy in 10 Days (2003)
★ 6.9/10
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and…
9
Breakin' All the Rules (2004)
★ 6/10
After being dumped by his model girlfriend, aspiring writer Quincy Watson quits his job and is inspired to pen the ultimate how-to book on breaking up. When it becomes a smash bestseller, he starts giving his player…
10
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…
11
Crossing Delancey (1988)
★ 5.9/10
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is…
12
Clueless (1995)
★ 7.2/10
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her…
13
Man's Favorite Sport? (1964)
★ 6.9/10
Roger Willoughby is a renowned fishing expert, who, unbeknownst to his friends, co-workers, or boss, has never cast a line in his life. One day, he crosses paths with Abigail Paige, a sweetly annoying girl who has just…
14
Swiped (2025)
★ 6.6/10
Whitney Wolfe uses extraordinary grit and ingenuity to break into the male-dominated tech industry.
15
Love, Guaranteed (2020)
★ 6.4/10
A lawyer takes on a new client that wants to sue a dating website because it guarantees love.
16
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.
17
Hitch (2005)
★ 6.6/10
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques…
18
The Map That Leads to You (2025)
★ 6.7/10
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
19
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.
20
Play It Again, Sam (1972)
★ 7.5/10
A neurotic film critic obsessed with the movie Casablanca attempts to get over his wife leaving him by dating again with the help of a married couple and his illusory idol, Humphrey Bogart.