by Fiona Underhill, Staff Writer

Those of us who love romance books are very familiar with the fake dating trope – where two people agree to pretend to date, or even marry, for mutually beneficial reasons – and the inevitable happens when real feelings become involved. The crueler side to the fake dating trope is when only of the two parties involved knows it’s fake, often because of a bet. This can be seen in classic literature like Dangerous Liaisons and its modern-day adaptation Cruel Intentions (1999). Fake Dating can also come out in other ways – such as two people on the run hide themselves by kissing–even Captain America (Chris Evans) and Black Widow (Scarlett Johansson) used this one in Captain America: The Winter Soldier (2014). My favorite twist on this trope is ‘Only One Bed,’ which is a whole sub-genre itself – it may surprise you to learn that versions of this trope appear as early as It Happened One Night (1934) and in Hitchcock’s The 39 Steps (1935). The British actor Matthew Goode became an expert in ‘Only One Bed’ in two romantic films with extremely similar plots–Chasing Liberty (2004) and Leap Year (2010).

As an introduction to Fake Dating Movies, I’m going to give you a rundown of my favorite 15 movies (in chronological order) that use this trope, which mostly consists of films where both parties agree–sorry no How To Lose a Guy in 10 Days (2003) here. There are a few notable exceptions, which I’ll explain as we go.

Older Movies (pre-1990)

Different versions of fake dating and arranged marriages (often because of gold-digging) comes up surprisingly often in the pre-code movies of the 30s and in screwball comedies of the 40s, such as The Lady Eve (1941), as well as in 50s musicals. The trope then mostly disappeared for the 60s and 70s, before reappearing in the high school movies of the 80s.

15. Come Live With Me (Clarence Brown, 1941)

Any movie which stars the stunningly beautiful Hedy Lamarr and the long, languid appeal of a young Jimmy Stewart is going to be well worth your time. Lamarr plays the magnificently-named Johnny Jones, a war-time exile from Vienna, who is under threat of deportation - unless she can marry an American citizen within a week. Impoverished writer Bill (Stewart) agrees, but only in exchange for bare minimum living expenses. The final act sees Bill and Johnny visit his grandmother’s house, where she realizes that he is the man for her – swoon.

14. Guys and Dolls (Joseph L. Mankiewicz, 1955)

While this rapturous, colorful musical does rely on ‘The Bet’ trope, the film as a whole is so wonderful, I’m going to forgive it. Much has been written about the incongruous Marlon Brando’s Sky Masterson, but I think Brando actually fits the role brilliantly, even if it was far from his usual comfort zone. His pairing with Jean Simmons’ Sarah Brown actually produces convincing (and quite sizzling) chemistry – especially in the delightful Havana sequence. Luck really is a lady here!

13. Overboard (Garry Marshall, 1987)

This extremely silly movie relies on the real-life chemistry between Kurt Russell and Goldie Hawn, and thankfully that is enough to power it through. Hawn’s pampered and pompous heiress falls from her yacht and suffers from amnesia. Russell’s blue collar carpenter takes advantage of this by making her believe she is his wife and mother of his four wildly unruly sons. Despite the outrageous plot, there are some real, tender moments between Hawn and the children, and with Russell, as she softens and grows to genuinely love them.

12. Can’t Buy Me Love (Steve Rash, 1987)

Long before he became McDreamy, Patrick Dempsey played a nerdy high schooler who decides to spend the $1,000 he’s been saving for a telescope on the most popular girl at school – if she’ll pretend to date him for a month. The nerd does become popular, but obnoxious along with it, so loses his friends and the girl. Yes, it’s a standard 80s high school comedy, but an enjoyable one with a strong cast. Watch out for Oz from Buffy (Seth Green) as Dempsey’s younger brother!

Hey-Day of the Rom-Com – the 90s and 2000s

The 90s and 2000s were the zenith of the rom-com, and romantic movies in general. Those of us who love this genre are still pining for those days, but there has been some hope in recent years – especially as 90s/00s stars such as Julia Roberts and Sandra Bullock have recently returned to the genre themselves.

11. Pretty Woman (Garry Marshall, 1990)

Probably the widely-agreed upon best example of the Fake Dating movie is this absolute classic. Handsome and rich businessman Richard Gere hires sex worker Julia Roberts to be his date at various high-stakes events (a polo match, dinner with important clients etc) while he’s in Los Angeles for work. Most women I know could give you a play-by-play of every moment, every line, every scene – it’s part of our DNA at this point. What a star-making role for Roberts and her megawatt smile.

10. Green Card (Peter Weir, 1990)

Written and directed by the great Australian Peter Weir, this is another Fake Dating (or marriage, in this case) movie that works because of the two leads, especially Andie MacDowell. This film has maybe my favorite ever movie apartment, thanks to the gorgeous greenhouse and roof garden. In fact, MacDowell’s character enters into the green card marriage specifically in order to secure this apartment, and that is entirely understandable. Weir’s writing and direction elevates this film above the usual 90s rom-com fare.

9. Dogfight (Nancy Savoca, 1991)

Fake Dating is not just a trope for rom-coms, and these next two movies show that romantic dramas can use the device more seriously. Considering that ‘The Bet’ trope is actually cruel and upsetting (it always makes me cry), it should be treated more seriously – as it is here, in Nancy Savoca’s Dogfight. Starring River Phoenix and Lili Taylor, this starts with a bunch of young marines making a bet to see who can bring the ugliest date to a dance, before they ship off to war. Considering it starts this way, the fact that we can still like Phoenix’s character and be rooting for the central couple, is a testimony to Bob Comfort’s screenplay, Phoenix and Taylor’s performances, and Savoca’s empathetic direction.

8. A Walk in the Clouds (Alfonso Arau, 1995)

Keanu Reeves stars in this swoony period romance, where he agrees to help pregnant Victoria (Aitana Sanchez-Gijon) by posing as her husband in front of her traditional family. The setting of California’s wine country in the 1940s really boosts the romantic atmosphere, and Reeves is absolutely adorable as a war veteran just trying to do the right thing by everybody, but who is clearly inwardly yearning for Victoria. This is a slightly lesser-known gem that uses the trope really well.

7. Ten Things I Hate About You (Gil Junger, 1999)

If there was one thing that the 90s were going to do, it was update a classic work of literature to a modern high school setting. In this case, it was Taming of the Shrew, with Julia Stiles as the feminist, Sylvia Plath-loving Kat and Heath Ledger as Australian bad boy Patrick. Patrick is paid to date Kate, but wooing her is an uphill battle which culminates with the classic serenading scene on the bleachers. With a great soundtrack, and a fantastic ensemble cast including Joseph Gordon-Levitt, this is still one of the most enduringly popular 90s movies today.

6. The Proposal (Anne Fletcher, 2009)

Sandy Bullock is second only to Julia Roberts as queen of the rom-com. In fact, she’s so powerful, she can even make a Ryan Reynolds movie appealing (I jest). Bullock plays a high-powered businesswoman who is, unfortunately, also Canadian, so she has to arrange a quick green card marriage to her long-suffering assistant – played by Reynolds. There’s some naked slapstick, there’s Betty White – it’s a fun movie!

Recent Gems from the last decade

5. Man Up (Ben Palmer, 2015)

This British rom-com stars Simon Pegg as Jack and Lake Bell (doing one of the best English accents an American actor has ever achieved) as Nancy. Nancy initially pretends to be Jack’s date, and then when she later reveals her deception, Jack recruits her to make his ex-wife jealous. Rory Kinnear almost steals the show as Nancy’s stalker Sean.

4. To All the Boys I’ve Loved Before (Susan Johnson, 2018)

If this were a ranking of the best Fake Dating movies, I would probably put this lovely gem second only to Pretty Woman – it really is that good. Lana Condor and Noah Centineo really struck chemistry lightning in a bottle with the first movie in a trilogy (which unfortunately tails off in quality). Peter Kavinsky drinking a milkshake in confusion, Peter Kavinsky spinning LJ by her back pocket, Peter Kavinsky saying “woah woah woah” – this film has so much to recommend it.

3. Holidate (John Whitesell, 2020)

Holiday-themed rom-coms are extremely variable in quality, but occasionally even a Netflick can offer up that elusive rewatchability factor. Australian actor Luke Bracey is the secret weapon here, playing a single guy who agrees to attend a series of weddings and family events with a single woman to keep the parental relationship pressure off their backs. I bet you can’t guess where this leads...

2. Purple Hearts (Elizabeth Allen Rosenbaum, 2022)

Another film that is a romantic drama, and definitely not a rom-com, is this Nicholas Sparks-style tale about a marine (Nicholas Galitzine) who marries an aspiring singer with diabetes (Sofia Carson), for the military and healthcare benefits. Although the drama is overwrought, the two leads sell it well and Galitzine displays the charm that he’d eventually use for Red, White & Royal Blue and The Idea of You.

1. Anyone But You (Will Gluck, 2023)

This updated spin on Much Ado About Nothing adds a fake dating dynamic to proceedings. Rising stars Glen Powell and Sydney Sweeney play Ben and Bea (see what they did there?) who are manipulated into dating by their families during a wedding in Australia, but decide to pretend to go along with it, as it benefits them. You may feel yourself resisting this movie as it’s happening, but by the time you’re watching the credits set to Natasha Bedingfield’s Unwritten, you’ll realize you’ve been swept along.

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