dating while weird and/or 40+
by happylooloo | created - 10 months ago | updated - 1 month ago | Public- Instant Watch Options
- Genres
- Movies or TV
- IMDb Rating
- In Theaters
- Release Year
- Keywords
1. Cyrus (I) (2010)
R | 91 min | Comedy, Drama, Romance
John and Molly, a divorced middle aged man and a single mother meet at a friends party and start up a small relationship, all John has to do now is meet Molly's son... Cyrus
Directors: Jay Duplass, Mark Duplass | Stars: John C. Reilly, Marisa Tomei, Jonah Hill, Catherine Keener
Votes: 36,613 | Gross: $7.46M
2. Me and You and Everyone We Know (2005)
R | 91 min | Comedy, Drama
A lonely shoe salesman and an eccentric performance artist struggle to connect in this unique take on contemporary life.
Director: Miranda July | Stars: John Hawkes, Miranda July, Miles Thompson, Brandon Ratcliff
Votes: 37,430 | Gross: $3.89M
3. Enlightened (2011–2013)
TV-MA | 28 min | Comedy, Drama
A self-destructive woman who has a spiritual awakening becomes determined to live an enlightened life, creating havoc at home and work.
Stars: Laura Dern, Diane Ladd, Sarah Burns, Luke Wilson
Votes: 10,207
4. Kajillionaire (2020)
R | 104 min | Comedy, Crime, Drama
A woman's life is turned upside down when her criminal parents invite an outsider to join them on a major heist they're planning.
Director: Miranda July | Stars: Richard Jenkins, Debra Winger, Evan Rachel Wood, Patricia Belcher
Votes: 22,105
5. Atypical (2017–2021)
TV-MA | 30 min | Comedy, Drama
Sam, an 18-year-old on the autism spectrum, decides it's time to find a girlfriend, which sets Sam's mom on her own life-changing path as her son seeks more independence.
Stars: Jennifer Jason Leigh, Keir Gilchrist, Brigette Lundy-Paine, Michael Rapaport
Votes: 103,544
6. Beef (2023– )
TV-MA | 352 min | Comedy, Drama
Two people let a road rage incident burrow into their minds and slowly consume their every thought and action.
Stars: Steven Yeun, Ali Wong, Joseph Lee, Young Mazino
Votes: 135,162
7. Undone (2019–2022)
TV-MA | 377 min | Animation, Drama, Fantasy
After she very narrowly survives a serious car accident, a woman discovers that she has a new relationship with time.
Stars: Rosa Salazar, Angelique Cabral, Constance Marie, Bob Odenkirk
Votes: 23,463
8. Single Drunk Female (2022–2023)
TV-14 | 23 min | Comedy, Drama
Follows Samantha Fink who, after a spectacularly embarrassing public breakdown, is forced to move back home with her overbearing mother to sober up and avoid jail time.
Stars: Sofia Black-D'Elia, Sasha Compère, Lily Mae Harrington, Garrick Bernard
Votes: 4,778
9. She-Hulk: Attorney at Law (2022)
TV-14 | 32 min | Action, Adventure, Comedy
Jennifer Walters navigates the complicated life of a single, 30-something attorney who also happens to be a green 6-foot-7-inch superpowered Hulk.
Stars: Tatiana Maslany, Ginger Gonzaga, Malia Arrayah, Jameela Jamil
Votes: 190,418
10. Deadpool (2016)
R | 108 min | Action, Comedy
A wisecracking mercenary gets experimented on and becomes immortal yet hideously scarred, and sets out to track down the man who ruined his looks.
Director: Tim Miller | Stars: Ryan Reynolds, Morena Baccarin, T.J. Miller, Ed Skrein
Votes: 1,125,739 | Gross: $363.07M
11. Eternal Sunshine of the Spotless Mind (2004)
R | 108 min | Drama, Romance, Sci-Fi
When their relationship turns sour, a couple undergoes a medical procedure to have each other erased from their memories forever.
Director: Michel Gondry | Stars: Jim Carrey, Kate Winslet, Tom Wilkinson, Gerry Robert Byrne
Votes: 1,078,118 | Gross: $34.40M
12. Welcome to Me (2014)
R | 87 min | Comedy, Drama
When Alice Klieg wins the Mega-Millions lottery, she immediately quits her psychiatric meds and buys her own talk show.
Director: Shira Piven | Stars: Kristen Wiig, James Marsden, Linda Cardellini, Wes Bentley
Votes: 19,648 | Gross: $0.61M
13. Lars and the Real Girl (2007)
PG-13 | 106 min | Comedy, Drama, Romance
A delusional young man strikes up an unconventional relationship with a doll he finds on the Internet.
Director: Craig Gillespie | Stars: Ryan Gosling, Emily Mortimer, Paul Schneider, R.D. Reid
Votes: 155,416 | Gross: $5.97M
14. Punch-Drunk Love (2002)
R | 95 min | Comedy, Drama, Romance
Socially frustrated Barry Egan calls a phone-sex line to curb his loneliness. Little does he know it will land him in deep trouble and will jeopardize his burgeoning romance with the mysterious Lena.
Director: Paul Thomas Anderson | Stars: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Jason Andrews
Votes: 177,484 | Gross: $17.84M
15. Baskets (2016–2019)
TV-MA | 30 min | Comedy, Drama
After failing at a prestigious French clowning college, Chip Baskets looks to keep his dream of becoming a professional clown alive.
Stars: Zach Galifianakis, Martha Kelly, Louie Anderson, Alex Morris
Votes: 12,871
16. I Heart Huckabees (2004)
R | 107 min | Comedy
A husband-and-wife team play detective, but not in the traditional sense. Instead, the happy duo helps others solve their existential issues, the kind that keep you up at night, wondering what it all means.
Director: David O. Russell | Stars: Jason Schwartzman, Jude Law, Naomi Watts, Mark Wahlberg
Votes: 66,277 | Gross: $12.78M
17. Elling (2001)
R | 89 min | Comedy, Drama
When his mother, who has sheltered him his entire 40 years, dies, sensitive would-be poet Elling is sent to live in a state institution. There he meets Kjell Bjarne, a gentle giant and ... See full summary »
Director: Petter Næss | Stars: Per Christian Ellefsen, Sven Nordin, Marit Pia Jacobsen, Jørgen Langhelle
Votes: 15,862 | Gross: $0.31M
18. The Song of Lunch (2010 TV Movie)
50 min | Drama, Romance
A London publisher recounts a lunchtime reunion with a former lover, in poetic monologue.
Director: Niall MacCormick | Stars: Alan Rickman, Emma Thompson, Andi Soric, Siubhan Harrison
Votes: 2,537
19. Alone Together (I) (2018)
TV-14 | 22 min | Comedy
Two not-so-young socially-awkward Millennials--rich, self-conscious, unmotivated Benji and his poor, freeloading, self-centered, strictly-platonic best friend Esther--try to fit in with L.A.'s vain, status-obsessed elite.
Stars: Esther Povitsky, Benji Aflalo, Edgar Blackmon, Chris D'Elia
Votes: 2,153
20. Hello I Must Be Going (2012)
R | 95 min | Comedy, Drama, Romance
Circumstances force a young divorcée to move back in with her parents in suburban Connecticut, where an affair with a younger guy rejuvenates her passion for life
Director: Todd Louiso | Stars: Melanie Lynskey, Christopher Abbott, Blythe Danner, John Rubinstein
Votes: 6,501 | Gross: $0.11M
21. Whiskey Tango Foxtrot (2016)
R | 112 min | Biography, Comedy, Drama
A journalist recounts her wartime coverage in Afghanistan.
Directors: Glenn Ficarra, John Requa | Stars: Tina Fey, Margot Robbie, Martin Freeman, Alfred Molina
Votes: 56,629 | Gross: $23.05M
22. Fallen Leaves (2023)
Unrated | 81 min | Comedy, Drama, Romance
In modern-day Helsinki, two lonely souls in search of love meet by chance in a karaoke bar. However, their path to happiness is beset by obstacles - from lost phone numbers to mistaken addresses, alcoholism, and a charming stray dog.
Director: Aki Kaurismäki | Stars: Alma Pöysti, Jussi Vatanen, Janne Hyytiäinen, Nuppu Koivu
Votes: 22,695
23. Jacqueline Novak: Get on Your Knees (2024)
94 min | Documentary, Comedy
Comedian Jacqueline Novak delivers a funny and philosophical meditation on sex, coming-of-age and a certain body part in this intimate stand-up special.
Director: Natasha Lyonne | Star: Jacqueline Novak
Votes: 657
24. Ladhood (2019–2022)
25 min | Biography, Comedy
A coming-of-age comedy from BAFTA-nominated comedian Liam Williams, who explores the roots of modern-day masculinity by delving into the memories of his own misspent adolescence.
Stars: Liam Williams, Oscar Kennedy, Samuel Bottomley, Aqib Khan
Votes: 1,135
25. Feel Good (2020–2021)
TV-MA | 315 min | Comedy, Drama, Romance
The series follows recovering addict and comedian Mae, who is trying to control the addictive behaviors and intense romanticism that permeate every facet of their life.
Stars: Mae Martin, Charlotte Ritchie, Phil Burgers, Jack Barry
Votes: 13,829
Tell Your Friends