Movies Like Chance of a Lifetime

If you liked Chance of a Lifetime (1998), a comedy and drama movie directed by Deborah Reinisch, 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
Love & Sex (2000)
★ 6.2/10Also comedy and drama
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back…
2
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
3
Enemies, a Love Story (1989)
★ 6.2/10Also comedy and drama
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
4
Numb (2007)
★ 5.9/10Also comedy and drama
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel…
5
Love Don't Co$t a Thing (2003)
★ 7.7/10Also comedy and drama
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
6
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
7
The Baltimorons (2025)
★ 6.3/10Also comedy and drama
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
8
Peace, Love & Misunderstanding (2011)
★ 5.8/10Also comedy and drama
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
9
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
10
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
11
Cyrus (2010)
★ 5.9/10Also comedy and drama
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…
12
L.A. Without a Map (1999)
★ 5.8/10Also drama and comedy
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a…
13
Young People Fucking (2007)
★ 5.9/10Also comedy and drama
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…
14
The Best You Can (2025)
★ 7/10Also comedy and romance
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside…
15
A California Christmas (2020)
★ 6.4/10Also comedy and romance
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
16
Irreplaceable You (2018)
★ 7/10Also comedy and drama
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
17
Just Before I Go (2015)
★ 6.4/10Also comedy and drama
Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he…
18
Delirious (2007)
★ 6.3/10Also comedy and drama
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…
19
XX/XY (2002)
★ 6/10Also drama and comedy
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
20
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…