Movies Like A Night in the Life of Jimmy Reardon

If you liked A Night in the Life of Jimmy Reardon (1988), a drama and romance movie directed by William Richert, 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
How to Please a Woman (2022)
★ 6.3/10Also romance and comedy
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
2
Strictly Sexual (2008)
★ 6.1/10Also drama and comedy
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.
3
Class (1983)
★ 6/10Also comedy and drama
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the…
4
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…
5
St. Elmo's Fire (1985)
★ 6.1/10Also drama and romance
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick…
6
Risky Business (1983)
★ 6.6/10Also romance and comedy
Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his…
7
Nothing Like the Holidays (2008)
★ 6.3/10Also comedy and drama
It’s Christmastime and the far-flung members of the Rodriguez family are converging at their parents’ home in Chicago to celebrate the season and rejoice in their youngest brother’s safe return from combat overseas.
8
Blind (2017)
★ 6.1/10Also drama and romance
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.
9
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.
10
White Palace (1990)
★ 6.7/10Also drama and romance
Max Baron is a Jewish advertising executive in his 20s who's still getting over the death of his wife. Nora Baker is a 40-something diner waitress who enjoys the wilder side of life. Mismatched or not, their attraction…
11
The Good House (2021)
★ 6.1/10Also romance and drama
When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person…
12
Meet Monica Velour (2010)
★ 5.8/10Also comedy and drama
For Tobe, a nerdy, horny, frizzy-haired cineaste who doesn't quite fit in with the average contemporary teen, the pinnacle of womanhood is Monica Velour, a soft-core actress who reached the zenith of her career in the…
13
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.
14
Winter Spring Summer or Fall (2024)
★ 7.3/10Also romance and drama
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
15
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…
16
Night Owls (2015)
★ 6.2/10Also drama and comedy
After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills…
17
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…
18
The Last Summer (2019)
★ 6/10Also romance and comedy
Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.
19
(Untitled) (2009)
★ 6.3/10Also drama and comedy
A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.
20
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…