Movies and Shows About Dating Struggles - Netflix Tudum

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    Ghosted? Take Comfort in These Shows and Movies About the Woes of Dating

    Swipe right on these streams for some commiseration.

    By Ananda Dillon
    Feb. 5, 2026

Ghosting, love bombing, breadcrumbing, catfishing, situationships: These days, dating should come with its own dictionary. From never-ending scrolling in the apps to awkward meetups and rampant emotional unavailability, the entire endeavor can be exhausting. When you’re feeling dating burnout and want to take a break, a show or movie about others in the same situation can bring the catharsis you crave. 

Of course, there are plenty of romantic things to watch if you want to cryto laugh, to renew your belief in love, to be a couch potato — or even if you just want to watch real people crash and burn like the rest of us. But if you want validation that you’re not the only one who feels like dating is a Sisyphean task, these shows and movies about the struggles of dating are here to sympathize. So take a night off from the madness and get ready to feel seen with these selections that showcase the often frustrating, certainly bumpy road to love.

Crazy, Stupid, Love.

Dating is hard at any age, but it can be especially challenging when one’s been out of the game for a while. Cal (Steve Carell) is sent reeling when his wife, Emily (Julianne Moore), asks for a divorce. At a bar where he goes to drown his sorrows, Cal meets Jacob (Ryan Gosling), a playboy skilled in the art of seduction. Jacob offers to help Cal, giving him a much-needed makeover and confidence boost. His efforts start to pay off with new women, and Cal’s changes are noticed by Emily, as well. But when Jacob starts dating Cal’s daughter, Hannah (Emma Stone), Cal struggles, judging the Casanova for his former behavior — while also benefiting from it.

Crazy, Stupid, Love.
1h 58m   PG-13   2011

Holidate

Among the many difficulties of dating is the pressure single people feel from family and friends to find love. As Sloane (Emma Roberts) endures yet another Christmas with her family’s judgment over her singleness, her promiscuous Aunt Susan (Kristin Chenoweth) introduces her to the idea of a “holidate”: a person whom she can bring to holiday functions but isn’t in a committed relationship with. When she meets Jackson (Luke Bracey), a golfer with a similar problem, they agree to be each other’s holidates for the next year. But at a certain point, the pretense starts to feel like something real.

Holidate
1h 44m   TV-MA   2020
Watch

Love Hard

In the online dating world, it’s all too easy to exaggerate and even downright lie about oneself. Natalie (Nina Dobrev), a dating columnist, learns this the hard way. After expanding her dating-app search radius, Natalie connects with Josh (Jimmy O. Yang), who lives in upstate New York, and quickly falls for him after months of phone calls and messages. She flies to his hometown to surprise him, only to find that Josh has catfished her and doesn’t look anything like his pictures. He begs her not to tell his family and to stay for the holidays and pose as his girlfriend. In exchange, he’ll introduce her to his friend Tag (Darren Barnet), whose pictures he used. Getting to know both men forces Natalie to confront whether she fell for Tag’s face or Josh’s personality.

Love, Guaranteed

Anyone who’s spent time searching, scrolling, and messaging in dating apps will appreciate this movie about a guy who wants to sue a dating service for not delivering on their promise. Nick (Damon Wayans Jr.) has gone on 986 dates and has not found a love match. Because the dating site is called “Love, Guaranteed,” he hires a lawyer, Susan (Rachael Leigh Cook), to help him sue the company. Habitually single, Susan tries going on a few dates herself to see whether it’s as hard as Nick claims and finds the process draining and defeating. The more time Susan and Nick spend working on the case, the more obvious it gets that feelings are developing — feelings that could jeopardize their entire case.

Oh, Hi!

Consider this common conflict in dating: alignment between both parties on relationship status. After four months of dating, Iris (Molly Gordon) feels confident in her relationship with Isaac (Logan Lerman), especially when he takes her on a romantic getaway to a farmhouse in the country. On their first night there, they experiment with handcuffing Isaac to the bed and, afterward, when Iris expresses her contentment with their relationship, Isaac springs on her that he hasn’t considered them to be official. In fact, he has been sleeping with other women. Fervent in her belief that they make a great couple, Iris leaves Isaac handcuffed, determined to convince him of their compatibility no matter what it takes.

The Perfect Date

Further proof that dishonesty will only lead to disaster in the dating world, this movie follows Brooks (Noah Centineo), a high school senior with his sights set on Yale. Worried about how he’ll afford the prestigious school, Brooks and his friend Murph (Odiseas Georgiadis), a tech genius, build an app that offers Brooks as a plus-one to women who’ll pay for a fake date. When Brooks starts to feel a little too comfortable pretending to be someone he’s not, feelings get hurt, and he risks losing his chance at a real connection.

Set It Up

Many dread the very idea of a blind date setup. The risk of catastrophe is just too high. But for two assistants to workaholic bosses, a successful setup may be the reprieve they so desperately need. Harper (Zoey Deutch) is an assistant to Kirsten (Lucy Liu), editor of a sports journalism publication. Charlie (Glen Powell) is an assistant to hard-headed venture capitalist Rick (Taye Diggs). When commiserating over whose boss is the hardest to work for, they joke that the two just need to get laid. Thus, a wild scheme kicks off to throw Kirsten and Rick together in an attempt to get them to date. After a few failed efforts, the plan starts to work, but keeping their bosses in a relationship will take all their resources.

To All the Boys I’ve Loved Before

Faking a relationship seems like the easiest form of dating — all the benefits, none of the work — but lying to others rarely goes well. Shy and romantic, Lara Jean (Lana Condor), a high school junior, feels lost without her college-bound sister, Margot (Janel Parrish) —especially when the secret letters she’s written to her old crushes over the years are somehow mailed out, with one going to her sister’s now ex-boyfriend, Josh (Israel Broussard). Lara strikes a deal with Peter (Noah Centineo), another of her former crushes who got a letter, to pretend to date her. This way, she can avoid Josh, and Peter can make his ex-girlfriend jealous in the hopes of getting her back. But avoiding problems only tends to exacerbate them.

Soulmates

What if there was a way to bypass dating altogether and be with the person who’s meant for you? This near-future sci-fi series features six stand-alone stories of people living in a world where a simple test can match you with your soulmate, provided that they too take the test. But it’s not all insta-love, as each story dives into the many questions of what a soulmate means and whether finding one is worth giving up a marriage or moving across the world — not to mention matching with someone who may not even be a good person. 

Woman of the Hour

Talk about a worst-case dating scenario. This movie, based on a horrifying true story, isn’t about your typical dating situation, and the stakes are life or death. Sheryl (Anna Kendrick) is an actress desperate for a break who agrees to appear on a dating game show for exposure. Uninterested in dating but making the most of the opportunity, she plays along, asking the three men hidden from her view various questions in order to choose a winner. Little does she know that one of the men is a wanted serial killer in the midst of a murder spree, and a date with him puts her very life in danger. 

 

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