Movies Like Holidate for casual arrangements that turn into real romance
Casual-arrangement rom-coms with plus-one deals, holiday check-ins, and feelings that sneak up.
Casual-arrangement rom-coms with plus-one deals, holiday check-ins, and feelings that sneak up.
Best first watch
Plus One (2019)
95% fit98 min · IMDb 6.6 · RT 88%
Ben and Alice run on the same casual-arrangement engine, a plus-one deal that keeps forcing them into intimate check-ins at public events. Andrew Rhymer and Jeff Chan keep the pacing loose and chatty, with wedding chaos replacing holiday rounds. Their feelings sneak up through bickering, hangovers, and the comfort of knowing each other's worst habits.
Watch if
Watch if you want the purest plus-one deal with sharp adult wedding chaos.
Skip if
Skip if endless wedding check-ins and messy hookup humor sound exhausting.
For you if
- You want adults who start with rules and slowly break every one of them.
- You enjoy flirtation that grows through repeat meetups, parties, and social obligations.
- You need a rom-com with real chemistry, brisk pacing, and some cheeky humor.
Not for you if
- You want sweeping melodrama or deeply sentimental love stories.
- You prefer very wholesome romance with little sex talk or adult messiness.
- You need a plot driven by big external stakes instead of relationship tension.
How Holidate (2020) alternatives compare
Pick Plus One or Love Hard if the fake-date deal is the main attraction. Choose Love Hard when you want Christmas on top. Go with Someone Great for stronger friend-group energy and breakup feelings. Set It Up is the cleanest workweek watch, with fast banter and lighter chaos. The Valet fits best if you want a bigger setup, public pressure, and a sweeter class-crossed romance.
How much is it built on a deal?
Deal drives everything
Holiday factor
Light seasonal feel
Friend-group energy
Mostly the main pair
Adult-humor edge
Sharp and messy
How much is it built on a deal?
Scheme in the middle
Holiday factor
Barely there
Friend-group energy
Small lively group
Adult-humor edge
Smart workplace banter
How much is it built on a deal?
Very little deal
Holiday factor
Barely there
Friend-group energy
Strong group hang
Adult-humor edge
Sharp and messy
How much is it built on a deal?
Deal drives everything
Holiday factor
Full Christmas mode
Friend-group energy
Mostly the main pair
Adult-humor edge
Sweeter than edgy
How much is it built on a deal?
Deal drives everything
Holiday factor
Barely there
Friend-group energy
Broad ensemble fun
Adult-humor edge
Broad adult laughs
Not ready to choose? Save these Modern Rom-Coms picks for later
Add all 5 to your watchlist in one tap — no account needed to start.
Not sure what to watch?
Date night
It keeps the plus-one deal front and center, then lets chemistry build through funny wedding disasters.
Quick watch
At 92 minutes, it moves fast and still lands adult humor, heartbreak, and warm friend check-ins.
Friend group
The celebrity cover-up and Antonio's family give it bigger laughs and more people to root for together.
Find your pick
Do you want the story to center on getting over a breakup, instead of building a new romance from scratch?
Moments you loved
Best movies like Holidate (2020)
1. Plus One (2019)
98 min · IMDb 6.6 · RT 88%
Ben and Alice run on the same casual-arrangement engine, a plus-one deal that keeps forcing them into intimate check-ins at public events. Andrew Rhymer and Jeff Chan keep the pacing loose and chatty, with wedding chaos replacing holiday rounds. Their feelings sneak up through bickering, hangovers, and the comfort of knowing each other's worst habits.
Watch if
Watch if you want the purest plus-one deal with sharp adult wedding chaos.
Skip if
Skip if endless wedding check-ins and messy hookup humor sound exhausting.
Where to watch
2. Set It Up (2018)
105 min · IMDb 6.5 · RT 92%
Claire Scanlon builds another modern rom-com around a deal, repeated check-ins, and chemistry that grows while two people insist they are managing logistics. Harper and Charlie spend their days plotting for their bosses, so the movie gets the same fast banter and adult work-life frustration. The feelings sneak up during cabs, late nights, and little acts of rescue.
Watch if
Watch if workplace banter and a clever deal beat big holiday antics for you.
Skip if
Skip if you want a true plus-one setup instead of office matchmaking.
Where to watch
3. Someone Great (2019)
92 min · IMDb 6.2 · RT 84%
Jennifer Kaytin Robinson keeps the adult-humor voice and contemporary dating mess, then shifts the hook from a plus-one deal to a breakup countdown across one last New York adventure. The check-ins come through Jenny, Blair, and Erin, which gives the movie a warmer friend-group pulse. Feelings sneak up from grief, memory, and the fear of starting over.
Watch if
Watch if adult-humor heartbreak and friend check-ins matter more than the deal.
Skip if
Skip if you need a full plus-one romance instead of breakup recovery.
Where to watch
4. Love Hard (2021)
105 min · IMDb 6.3 · RT 50%
This one leans hardest into the holiday side of the angle, with a fake-girlfriend arrangement and Christmas check-ins built around a dating-app lie. Hernán Jiménez keeps it bright and brisk, while Natalie, Josh, and Tag turn the setup into a triangle full of awkward errands and family pressure. The feelings sneak up once the deal starts creating real intimacy.
Watch if
Watch if Christmas check-ins and a fake-girlfriend deal sound like your sweet spot.
Skip if
Skip if catfish lies and broad holiday awkwardness kill the mood.
Where to watch
5. The Valet (2022)
123 min · IMDb 6.7 · RT 75%
Like any good casual-arrangement rom-com, this starts with a public cover story and then keeps tightening the screws through staged dates, media appearances, and private check-ins. Richard Wong uses celebrity chaos and class contrast to widen the world around Olivia and Antonio. The feelings sneak up because the deal asks them to perform closeness until it stops feeling fake.
Watch if
Watch if you like fake-couple deals with class friction and public chaos.
Skip if
Skip if celebrity scandal plots feel louder than intimate holiday check-ins.
Where to watch
Beyond movies
TV shows and books that scratch the same itch
Lovesick
This series lives in the modern rom-com lane, with messy dating rules, awkward check-ins, and feelings that build over time between friends who keep circling the real issue. It matches Holidate through casual setups that turn into genuine attachment, plus a light, sharp style that avoids secondhand embarrassment.
Available for purchase on Prime Video and Apple TV+ and Google Play and Fandango
Starstruck
Starstruck is a contemporary romantic comedy built on a fling that keeps reopening under new terms, which fits the plus-one-deal energy of Holidate. It has the same breezy dating-world feel, with dry humor, holiday and event-driven reunions, and a slow realization that the arrangement has become real.
Prime Video and Max
Love Life
Love Life fits the hub because it tracks adult relationships with a current, funny, emotionally easygoing approach instead of broad cringe. Like Holidate, it focuses on dating patterns, convenient arrangements, and the way repeated check-ins and shared routines can quietly turn into something deeper.
Available for purchase on Prime Video and Google Play and Fandango
The wedding date
by Jasmine Guillory
Like Holidate, this contemporary romance starts with an event-driven fake date that feels casual at first, then turns real once Alexa and Drew try to return to their separate lives. The wedding-plus-one setup, flirty banter, and grown-up long-distance complications fit the sharp, modern rom-com lane.
Available at major bookstores
Common questions about movies like Holidate (2020)
What is the best movie like Holidate (2020)?
Based on our analysis, Plus One (2019) is the closest match with a 95% fit score. See the full breakdown above for why it earned the top spot.
Which of these works best for couples where one person likes romance more than the other?
Start with Plus One or Set It Up. Both keep the romance grounded in banter, work stress, and recognizable dating fatigue, so a skeptical partner still gets jokes and momentum. The Valet also works if you want a bigger setup and more public chaos.
Which one should I avoid if awkward lies or breakup pain hit too hard?
Someone Great hits the hardest if breakup pain is raw, because Jenny's night out keeps circling old memories. Love Hard and The Valet ask you to sit with a lot of deception before the romance settles in. Plus One is messy too, though its wedding humor keeps things looser.
What should I pick if I want to end the night feeling light?
Love Hard is the easiest warm-up watch when you want Christmas comfort and a soft landing. Set It Up also leaves a light, upbeat feeling, with less emotional ache than Someone Great. Pick Plus One if you want more bite in the jokes along the way.
Which is the easiest weeknight watch when I'm tired?
Someone Great is the quickest at 92 minutes, and it starts moving right away. Plus One is also easy to fit into a weeknight and has a relaxed hangout pace. The Valet asks for the most time and a little more patience because its setup is broader and longer.
Which feels sharpest, and which feels sweetest?
Plus One feels sharpest and most adult, with wedding-season fatigue and two people who know exactly how to push each other. Love Hard is the sweetest of the bunch. Someone Great leans bittersweet, while The Valet goes bigger and broader with celebrity scandal and family scenes.
Where should I start if I want the clearest version of this plus-one setup?
Begin with Plus One if you want the cleanest read on this page's promise, since the whole movie runs on a plus-one deal. Move to Love Hard if the holiday angle matters most. Pick Set It Up first if you prefer workplace chaos over fake dating.
Was this list useful?
Quick feedback helps us improve ranking quality.