Movies Like Kiss and Tell

If you liked Kiss and Tell (2015), a movie directed by Clinton Cornwell, 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
Elizabethtown (2005)
★ 6.2/10
Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when…
2
Grandma (2015)
★ 6.4/10
Self-described misanthrope Elle Reid has her protective bubble burst when her 18-year-old granddaughter, Sage, shows up needing help. The two of them go on a day-long journey that causes Elle to come to terms with her…
3
Autumn in New York (2000)
★ 6.1/10
Will Keane, a Manhattan restaurateur, is content with his playboy lifestyle until he meets Charlotte Fielding, a free-spirited young woman. Together the pair pursue a passionate affair that forces them both to…
4
The Way Way Back (2013)
★ 7.1/10
Shy 14-year-old Duncan goes on summer vacation with his mother, her overbearing boyfriend, and her boyfriend's daughter. Having a rough time fitting in, Duncan finds an unexpected friend in Owen, manager of the Water…
5
A Lot Like Love (2005)
★ 6.8/10
On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they…
6
Brief Encounter (1945)
★ 7.7/10
Returning home from a shopping trip to a nearby town, bored suburban housewife Laura Jesson is thrown by happenstance into an acquaintance with virtuous doctor Alec Harvey. Their casual friendship soon develops during…
7
Good Luck Chuck (2007)
★ 5.9/10
Cursed since childhood, dentist Charlie Logan cannot find the right woman. Even worse, he learns that each of his ex-girlfriends finds true love with the man she meets after her relationship with him ends. Hearing of…
8
(500) Days of Summer (2009)
★ 7.3/10
Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went…
9
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
10
Prime (2005)
★ 6/10
A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.
11
Ode to Joy (2019)
★ 6.1/10
Charlie suffers from a serious disease that causes acute narcolepsy whenever he is happy. Although he develops a variety of techniques to deny himself pleasure and deal with his sleep issues, they’re put to the test…
12
Daddio (2024)
★ 6.3/10
A woman taking a cab ride from JFK airport engages in a conversation with the driver about the important relationships in their lives.
13
Whatever Works (2009)
★ 7.1/10
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are…
14
Leap Year (2010)
★ 6.9/10
When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her…
15
Friends with Kids (2012)
★ 5.9/10
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can…
16
Thumbsucker (2005)
★ 6.2/10
Justin Cobb, a teenager in suburban Oregon, copes with his thumb-sucking problem, romance, and his diagnosis with ADHD and subsequent experience using Ritalin.
17
No Hard Feelings (2023)
★ 6.7/10
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To…
18
Midnight Sun (2018)
★ 7.8/10
Katie, a 17-year-old, has been sheltered since childhood and confined to her house during the day by a rare disease that makes even the smallest amount of sunlight deadly. Fate intervenes when she meets Charlie and…
19
Author! Author! (1982)
★ 6/10
A broadway playwright is burning the candle at both ends. He is dealing with pressure from a production nearing premiere, a wife who is leaving him, and 5 children 4 of which belong to her.
20
Blue Valentine (2010)
★ 7/10
Dean and Cindy live a quiet life in a modest neighborhood. They appear to have the world at their feet at the outset of the relationship. However, his lack of ambition and her retreat into self-absorption cause…