Some of the most memorable love stories don’t start with a perfect first date.
They start with jet lag, a wrong house, a delayed flight, or a holiday that was supposed to be “just a break.” If you liked The Holiday and the whole “trip changes your life” vibe, these five films are very much in that lane: travel, chance meetings, emotional chaos, and people figuring themselves out while their hearts are busy doing something completely different.
Join the leading dating site that prepared a review. Below are 5 relationship-focused films, from a modern classic to some of the newest rom-coms, all built around trips, swaps or destination drama.
1. The Holiday (2006) – The House Swap That Started It All
We kind of have to start here, right?
Two women, two continents, one terrible December. Iris is a British journalist hopelessly in love with a man who treats her like a backup plan. Amanda is a high-powered American trailer editor who just discovered her boyfriend is cheating. Both are exhausted, heartsick and desperate for a reset.
On a home-swap website they find each other, and within days Iris is in a huge Los Angeles mansion while Amanda is freezing in a tiny English cottage. Each place comes with surprise humans: Iris meets Amanda’s charming colleague and an elderly screenwriter who basically becomes her therapist; Amanda crashes into Iris’s brother, a widowed dad with his own emotional mess.
Is it realistic? Of course not. Is it deeply comforting? Absolutely. Under all the cosy Christmas lights, it’s about something real: sometimes you have to physically leave your old life to see what you actually deserve.
2. Your Place or Mine (2023) – Grown-Up House Swap With Kids, Careers & History
Think of this as The Holiday’s sleep-deprived, modern cousin.
Debbie and Peter hooked up once, decades ago, and somehow ended up best friends instead of lovers. She’s a single mum in Los Angeles, careful and organised, trying to hold everything together. He’s a bachelor in New York, allergic to long-term commitment but very good at talking Debbie through her crises.
When Debbie needs to be in New York for a course, they swap lives for a week: she stays in his minimalist Brooklyn apartment, he moves into her cluttered LA house to look after her son. It’s not really a “holiday”; it’s more like stepping into the other person’s reality.
The nice thing about this film is that the romance grows through small details. Debbie discovers sides of Peter she never took seriously before; Peter realises how much weight Debbie carries and how much he actually cares about her kid. It feels less like a fantasy and more like the messy, late-thirties version of “wait… have we been in love this whole time?”
3. Love at First Sight (2023) – Airplane Chemistry & London Serendipity
If you’ve ever had a surprisingly deep conversation with a stranger on a plane and thought, “If this were a movie…”, this is literally that movie.
Hadley misses her flight to London by four minutes, gets rebooked, and ends up next to Oliver, a statistics-obsessed Brit in a perfectly pressed shirt. They share a long overnight flight, talk about families, fears, weird little details… and by the time they land, there’s a connection. Not just “you’re cute”, but “I actually see you.”
And then, in true airport style, they get separated at passport control.
The rest of the story plays with chance and timing: big London events, family drama, and the question of whether one intense meeting is enough to actually change the path of your life. It’s romantic, obviously, but it also deals with grief and complicated parents in a way that hits harder than you’d expect from something with “love at first sight” in the title.
Bonus: London looks gorgeous and strangely small, the way it always does when a film wants two people to keep accidentally bumping into each other.
4. Ticket to Paradise (2022) – Divorced Parents, Bali & a Second Chance
Not all travel-romance stories are about young people finding their first love. Sometimes they’re about older people realising they might not be finished with each other after all.
In Ticket to Paradise, David and Georgia are divorced exes who can barely manage to be polite at their daughter’s graduation. Years of resentment sit between them like a third person at the table. Then their daughter goes on a trip to Bali, falls head-over-heels for a local seaweed farmer, and announces she’s staying and getting married.
David and Georgia, convinced she’s about to ruin her life the way they “ruined” theirs, fly to Bali with one mission: sabotage the wedding.
Obviously, Bali has other plans. Surrounded by tropical scenery, rituals, family warmth and their daughter’s very real happiness, the two of them start to soften. They remember who they used to be before they turned into “my horrible ex.” The film is basically: divorced enemies to… something softer, set against ridiculous views and chaotic family events.
It’s funny, a bit over the top, and surprisingly sweet about middle-aged love and regret.
5. Anyone But You (2023) – Enemies, a Sydney Wedding & Fake Dating Mayhem
If you want something louder, more chaotic and totally aware that it’s a rom-com, this one is it.
Bea and Ben have one amazing first date, the kind where you talk for hours and everything feels easy. Then a misunderstanding blows everything up, and they both walk away convinced the other person is awful. Months later, they end up at the same destination wedding in Sydney, surrounded by relatives, exes, and people who really, really want them to be together.
To survive the weekend and dodge some awkward situations, they agree to pretend they’re a couple. Obviously, because this is a romantic comedy and not real life, pretending starts to feel a bit too real.
This film leans hard into tropes: enemies to lovers, forced proximity, fake dating, dramatic declarations in pretty locations. But it does it with a wink, bright colours and a lot of physical comedy. Sydney becomes part of the story – beaches, boats, big houses – turning the whole thing into a chaotic holiday you’re weirdly glad you’re only watching.
Why These Travel-Flavoured Love Stories Hit So Much
On the surface, all five movies are a bit ridiculous. People swap houses with strangers, meet soulmates on planes, crash weddings on tropical islands, or fall back in love while pretending to date. If you describe them out loud, they sound like something you’d roll your eyes at.
But they work because they tap into something very human:
- Change of place = change of self.
When you’re pulled out of your normal routine, you notice things you usually ignore: what you actually want, who you miss, which parts of your life are just habit. - Timing and accidents matter.
A missed flight, a last-minute decision, a random invite to a wedding – in real life these things probably don’t lead to a movie-worthy romance, but we all know they could. That “it almost didn’t happen” feeling is powerful. - Love is rarely tidy.
None of these relationships follow a clean, logical path. People misread each other, get scared, run away, try again. It’s exaggerated, sure, but it reflects the way real relationships have phases, detours and “we’re not talking right now” periods.
So if you’re in the mood for films that mix feelings with scenery – broken hearts and new cities, bad decisions and plane tickets – any of these five will do the job. Pick one, grab a blanket, and let someone else’s messy holiday romance remind you that your own love life is allowed to be complicated too.
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