Movies Like Love, Loss, and What I Wore

If you liked Love, Loss, and What I Wore (2020), a movie directed by Karen Carpenter, 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
All About Nina (2018)
★ 5.8/10
Nina Geld's passion and talent have made her a rising star in the comedy scene, but she's an emotional mess offstage. When a new professional opportunity coincides with a romantic one, she is forced to confront her own…
2
Someone Great (2019)
★ 6.4/10
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one…
3
Madeline's Madeline (2018)
★ 5.9/10
Madeline has become an integral part of a prestigious physical theater troupe. When the workshop's ambitious director pushes the teenager to weave her rich interior world and troubled history with her mother into their…
4
Now and Then (1995)
★ 6.9/10
Waxing nostalgic about the bittersweet passage from childhood to puberty, four childhood girlfriends — Teeny, Chrissy, Samantha and Roberta — recall the magical summer of 1970. During their walk down memory lane, they…
5
Theater Camp (2023)
★ 6.4/10
After the indomitable and beloved founder of a scrappy theater camp in upstate New York falls into a coma, the eccentric staff must band together with her clueless "crypto-bro" son to keep the thespian paradise afloat.
6
The Rose Tattoo (1955)
★ 6.9/10
A grieving widow embarks on a new romance when she discovers her late husband had been cheating on her.
7
Alfie (2004)
★ 5.9/10
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
8
Carrie Fisher: Wishful Drinking (2010)
★ 7.3/10
"Wishful Drinking" is based on Fisher's memoirs of the same title. The stage adaptation had its world premiere in 2006 at the Geffen Playhouse in L.A. It later played at Berkeley Repertory before opening on Broadway in…
9
Much Ado About Nothing (2011)
★ 8.3/10
Two young lovers, Claudio and Hero, are to be married imminently but the devious scheming of a resentful Prince looks set to thwart the nuptials. Meanwhile, marriage seems inconceivable for reluctant lovers Beatrice…
10
She's Funny That Way (2015)
★ 5.9/10
On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.
11
Oh, Hello on Broadway (2017)
★ 6.9/10
Two delusional geriatrics reveal curious pasts, share a love of tuna and welcome a surprise guest in this filming of the popular Broadway comedy show.
12
The Golden Coach (1952)
★ 7.1/10
A viceroy, a nobleman and a bullfighter court a comedy-troupe actress in 18th-century Peru.
13
Hello, Dolly! (1969)
★ 7/10
Dolly Levi is a strong-willed matchmaker who travels to Yonkers, New York in order to see the miserly "well-known unmarried half-a-millionaire" Horace Vandergelder. In doing so, she convinces his niece, his niece's…
14
Feel the Beat (2020)
★ 7.5/10
After failing to make it on Broadway, April returns to her hometown and reluctantly begins training a misfit group of young dancers for a competition.
15
Julia (1977)
★ 6.5/10
At the behest of an old and dear friend, playwright Lillian Hellman undertakes a dangerous mission to smuggle funds into Nazi Germany.
16
Real Women Have Curves (2002)
★ 6.1/10
In East Los Angeles, an 18-year-old struggles between her ambitions of going to college and the desires of her domineering mother for her to get married, have children, and oversee the small, rundown family-owned…
17
National Theatre Live: Fleabag (2019)
★ 7.8/10
Fleabag may seem oversexed, emotionally unfiltered and self-obsessed, but that's just the tip of the iceberg. With family and friendships under strain and a guinea pig café struggling to keep afloat, Fleabag suddenly…
18
The Trials of Cate McCall (2013)
★ 6.4/10
In order to be reinstated to the bar and recover custody of her daughter, a hotshot lawyer, now in recovery and on probation, must take on the appeal of a woman wrongfully convicted of murder.
19
Tootsie (1982)
★ 7.2/10
When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.
20
Bullets Over Broadway (1994)
★ 7.1/10
After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a…