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7 Movies Like ‘Fleishman is in Trouble’ To Watch If You Like the Series

Movies Like Fleishman is in Trouble
Credit - FX

Jesse Eisenberg, Lizzy Caplan, and Claire Danes are back in the FX new series Fleishman is in Trouble. The FX series is based on New York Times bestselling novel by Taffy Brodesser-Akner and it follows Toby Fleishman (Eisenberg), a middle-aged man who is just dipping his foot in the dating pool after his divorce. Fleishman quickly gets on the online dating scene and fully throws himself in, and in turn, he finds out that a lot of women like him. The divorcee is all set to ship off on his first single summer adventure in decades, but all of his plans are quickly scrapped, as his ex-wife suddenly disappears into thin air and leaves their children with him. So, if you liked the Eisenberg miniseries here are some movies you should watch next.

The Squid and the Whale (Starz)

Movies Like Fleishman is in Trouble
Credit – Sony Pictures

Synopsis: In his third feature, director Noah Baumbach scores a triumph with an autobiographical coming-of-age story about a teenager whose writer-parents are divorcing. The father (Jeff Daniels) and mother (Laura Linney) duke it out in half-civilized, half-savage fashion, while their two sons adapt in different ways, shifting allegiances between parents. The film is squirmy-funny and nakedly honest about the rationalizations and compensatory snobbisms of artistic failure as well as the conflicted desires of adolescents for sex and status. In detailing bohemian-bourgeois life in brownstone Brooklyn, Baumbach is spot on. Everyone proceeds from good intentions and acts rather badly, in spite or because of their manifest intelligence. Fulfilling the best traditions of the American independent film, this quirky, wisely written feature explores the gulf between sexes, generations, art and commerce, Brooklyn and Manhattan.

Blue Valentine (Prime Video)

Movies Like Fleishman is in Trouble
Credit – The Weinstein Company

Synopsis: Academy-Award-nominees Ryan Gosling (Half Nelson, The Notebook) and Michelle Williams (Brokeback Mountain, Shutter Island) star in Blue Valentine, an intimate, shattering portrait of a disintegrating marriage. Once passionately in love, Dean (Gosling) and Cindy (Williams) try to rekindle their lost feelings by spending a night in a hotel, remembering what brought them together six years earlier. Moving between the present and the past courtship of these two, this award-winning movie captures both the promise of new romance and the brutal heartbreak that comes with fading love.

Marriage Story (Netflix)

Movies Like Fleishman is in Trouble
Credit – Netflix

Synopsis: Marriage Story is Academy Award nominated filmmaker Noah Baumbach’s incisive and compassionate portrait of a marriage breaking up and a family staying together. The film stars Scarlett Johansson and Adam Driver. Laura Dern, Alan Alda, and Ray Liotta co-star.

Scenes from a Marriage (HBO Max)

Movies Like Fleishman is in Trouble
Credit – SVT

Synopsis: Scenes from a Marriage chronicles the many years of love and turmoil that bind Marianne (Liv Ullmann) and Johan (Erland Josephson), tracking their relationship as it progresses through a number of successive stages: matrimony, infidelity, divorce, and subsequent partnerships. Originally conceived as a five-hour, six-part television miniseries, the film is also presented in its three-hour theatrical cut. Shot on 16 mm in intense, intimate close-ups by cinematographer Sven Nykvist and featuring flawless performances by Ullmann and Josephson, Bergman’s emotional X-ray reveals the intense joys and pains of a complex bond.

Crazy, Stupid, Love (Rent on Prime Video)

Movies Like Fleishman is in Trouble
Credit – Warner Bros.

Synopsis: At forty-something, straight-laced Cal Weaver (Steve Carell) is living the dream—good job, nice house, great kids and marriage to his high school sweetheart. But when Cal learns that his wife, Emily (Julianne Moore), has cheated on him and wants a divorce, his “perfect” life quickly unravels. Worse, in today’s single world, Cal, who hasn’t dated in decades, stands out as the epitome of un-smooth. Now spending his free evenings sulking alone at a local bar, the hapless Cal is taken on as wingman and protégé to handsome, thirty-something player Jacob Palmer (Ryan Gosling).

In an effort to help Cal get over his wife and start living his life, Jacob opens Cal’s eyes to the many options before him: flirty women, manly drinks and a sense of style that can’t be found at Supercuts or The Gap. Cal and Emily aren’t the only ones looking for love in what might be all the wrong places: Cal’s 13-year-old son, Robbie, is crazy about his 17-year-old babysitter, Jessica, who harbors a crush on Cal. And despite Cal’s makeover and his many new conquests, the one thing that can’t be made over is his heart, which seems to keep leading him back to where he began.

Stuck in Love (Peacock & Prime Video)

Movies Like Fleishman is in Trouble
Credit – Millennium Entertainment

Synopsis: Three years past his divorce, veteran novelist Bill Borgens (Academy Award® nominee Greg Kinnear) can’t stop obsessing over, let alone spying on, his ex-wife Erica (Academy Award® winner Jennifer Connelly), who ignominiously left him for another man. Even as his neighbor-with-benefits, Tricia (Kristen Bell) tries to push him back into the dating pool, he remains blind to anyone else’s charms. Meanwhile, his fiercely independent collegiate daughter Samantha (Lily Collins) is publishing her first novel while recoiling at the very thought of first love with a diehard romantic (Logan Lerman); and his teen son Rusty (Nat Wolff) is trying to find his voice, both as a fantasy writer and as the unexpected boyfriend of a dream girl with unsettlingly real problems. As each of these situations mounts into a tangled trio of romantic holiday crises, it brings the Borgens to surprising revelations about how endings become beginnings.

(500) Days of Summer (HBO Max)

Underrated Joseph Gordon-Levitt Movies
Credit – Searchlight Pictures

Synopsis: Boy meets girl. Boy falls in love. Girl doesn’t. This post modern love story is never what we expect it to be — it’s thorny yet exhilarating, funny and sad, a twisted journey of highs and lows that doesn’t quite go where we think it will. When Tom, a hapless greeting card copywriter and hopeless romantic, is blindsided after his girlfriend Summer dumps him, he shifts back and forth through various periods of their 500 days “together” to try to figure out where things went wrong. His reflections ultimately lead him to finally rediscover his true passions in life.

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