LUCKY IN LOVE! THE LUCKY & FUN 13 ROMANCE MOVIES
Every once in a while, I take a look at the “made up” or silly holidays for any given date. I used to do this quite a lot when I’d create bookstagram challenges (which is a throwback). But, more to the point, this week as I struggled to come up with content to create, I decided to do a bit of a quick Internet search. That resulted in the discovery that today is one of those silly days which is “Lucky Penny Day.” Naturally, this got me thinking and I decided to put together a list of “romantic lucky in love movies” or at least some that would appeal to that kind of sentiment.
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LUCKY IN LOVE MOVIES! 13 ROMANCE MOVIES #Movies #FunnyMovies #ComedyMovies Share on XThis is why I bring you this list of titles to look through and possibly enjoy tonight, or any day you’re wanting something fun and silly. Let’s check out what makes the feature.
ROMANTIC LUCKY in LOVE MOVIES
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I can admit I don’t remember this angsty drama with Jim Sturgess at all. But I know I did see it, and it involves a type of heist involving winning big in Vegas. (PG-13)
Synopsis: Academy Award Winner Kevin Spacey (The Usual Suspects) and young Hollywood super star Kate Boswoth (Superman Returns) star in this clever & adreniline filled heist film. An MIT math whiz is recruited by a teacher to join a specialized team of card counters. They break away from their mentor before casino security finally catches up with them. – via Prime Video
Digitally purchase on places like Prime Video
HONEYMOON in VEGAS
Never saw this one, but it has a young Sarah Jessica Parker and sounds like it may be a fun little film. It’s about a man who agrees for his fiancée to spend time with the man he owes a gambling debt to. (PG-13) romantic lucky in love movies
Synopsis: When a man loses $65,000 to a wealthy gambler, he agrees to let him spend a romantic Hawaii getaway with his fiancée to pay off his debt. – via Prime Video
Digitally purchase on places like Prime Video
IT COULD HAPPEN to YOU
It’s been years since last I saw this, but I do remember it being a sweet 90s rom-com about a cop who splits a lottery ticket with a down-on-her-luck waitress. The movie often comes under fire, and I don’t see a lot of people talking about it, but it is a cute one in spite of its flaws. Nicholas Cage stars. (PG)
Synopsis: Nicolas Cage, Bridget Fonda and Rosie Perez star in this irrepressible romantic comedy inspired by the true story of a humble cop who leaves a two million dollar tip to a hard-luck waitress. Charlie Lang (Cage) is a neighborhood cop with a heart of gold, and a money-hungry wife Muriel (Perez) who’s always looking for a way to cash in. – via Prime Video
Stream with Hulu; or digitally purchase on places like Prime Video
JUST MY LUCK
This one is pretty obvious, but it’s just too cute not to include. Lindsey Lohan stars as a career woman who doesn’t know bad luck (and is quickly rising up the ranks in her career), until she does! She discovers that a hapless New Yorker who somehow obtains her lucky streak. (PG-13)
Synopsis: Sexy Manhattanite Ashley (Lindsay Lohan) is known to many as the luckiest woman around. After a chance encounter with a down and out young man (Chris Pine), however, she realizes that she’s swapped her fortune for his. – via Prime Video
Stream with Tubi; or digitally purchase on places like Prime Video
LUCKY in LOVE (2014)
A Hallmark premiere, this one features Jessica Schor and Benjamin Hollingsworth in an adorable best friends rom-com. The film has Schor playing a successful career woman falling for a charming, handsome man, while her bestie watches. (TV-G) romantic lucky in love movies
Synopsis: A woman must adjust to her new, seemingly perfect life when her pranks on April Fools’ Day come true. – via Hallmark+
Stream on Hallmark+
THE LUCKY ONE
Unlike some of these, this one is more heavy. Based on the novel by Nicholas Sparks, it follows a soldier (Zac Efron) who believes a photo he finds is his lucky charm. Of course, he ends up meeting the women in the photo. (PG-13)
Synopsis: Zac Efron is a war vet who tracks down a woman from a photo that he believes kept him alive during battle. – via Prime Video
Stream with Tubi; or digitally purchase this film on places like Prime Video
MEET ME in LAS VEGAS
Never seen this 50s romantic-comedy but Cyd Charisse stars. The film follows a rancher who’s normally bad yearly trip to Vegas changes after he meets a ballerina. (PG)
Synopsis: Ever since rancher Chuck Rodman grabbed the hand of a passing ballerina, he can’t lose. – via Prime Video
Rent or purchase digitally on places like Prime Video
OCEAN’S TWELVE
Ok, so these titles aren’t super romance-y per se, but ‘12’ is the most of the three films. It teases up the happy end (more so) between Danny and Tess, and has a new little cat-and-mouse romance involving Brad Pitt’s character. Catherine Zeta-Jones co-stars in this one that’s full of more con fun! (PG-13) romantic lucky in love movies
Synopsis: After splitting the $160 million take, each of the infamous Ocean’s crew have tried to go straight, lay low and live a legit life … but that’s proven to be a challenge. – via Prime Video
Stream with Starz; or purchase digitally on places like Prime Video
A RING by SPRING (2014)
When a fortune teller informs a successful career woman that she won’t marry unless she receives a ring (by spring), she sets out to make her own luck. (TV-G)
Synopsis: A fiercely independent single woman is forced to consider marrying her not-so-perfect boyfriend when a gypsy fortuneteller convinces her she must be engaged by the spring or risk a lifetime alone. – via Hallmark+
Stream on Hallmark+
SIMPLY IRRESISTABLE
To be honest, I cannot remember if I’ve seen this film or not. I think I did, but clearly I didn’t find it super memorable. It follows a chef, only instead of a penny or fairy godmother, her good luck charm is a crab! (PG-13)
Synopsis: A department store executive tries to resist falling in love with a young woman, who he believes possess magical powers after inheriting a restaurant. – via Prime Video
Stream on Plex or Prime Video; or rent or purchase digitally on places like Prime Video
WHAT HAPPENS in VEGAS
Cameron Diaz co-stars with Ashton Kutcher in this romp about two people who detest each other, drunkenly marry in Vegas, and then, luckily end up winning a fortune. Trouble is, their married, so who’s money is it really? (PG-13) romantic lucky in love movies
Synopsis: A wild night in Vegas leads to an ill-fated marriage for New York singles. – via Prime Video
Stream on Hulu or Peacock; or purchase digitally on places like Prime Video
WHEN in ROME
A woman (Kristen Bell) takes a handful of coins from an Italian fountain little realizing that by doing so, the giver of those coins will all fall in love with her. This one is really quite silly, and the first few times I saw it, it never 100% wins me over. However, I have since come to thoroughly appreciate this film and love its simple and joyful story. (PG-13)
Synopsis: When Beth, an unlucky-in-love New York curator, takes a whirlwind trip to Rome for her sister’s wedding, an unexpected crush takes her by surprise. – via Prime Video
Stream on Hulu or Netflix; or rent or purchase digitally on places like Prime Video
WIN a DATE with TAD HAMILTON
This darling 2000s (albeit silly) rom-com features Topher Grace (now in ABC’s Home Economics) with Kate Bosworth in a film about a small town girl who wins a date with Hollywood’s biggest celebrity. It’s so cute it’s a smile-so-big-it-hurts kind of romance. (PG-13)
Synopsis: Rosalee, star-struck small-town girl wins a date with the Hollywood hunk Tad Hamilton. And while it may be Rosalee’s dream-come-true, it means complete chaos for her best friend Pete. – via Prime Video romantic lucky in love movies
Stream with MGM+, Paramount+ or with Tubi; or purchase digitally on places like Prime Video
BONUS! LUCKY YOU
This one follows Eric Bana’s unlucky poker player and the romance he begins to develop with a pretty singer. (PG-13)
Synopsis: A gifted gambler participates in the Poker World Series in Las Vegas, where he will meet a woman that will change his life. – via Prime Video
Purchase digitally on places like Prime Video
What movies do you like that would fit this topic? Have you seen any of these romantic lucky in love movies from this list? Did you like or dislike the ones you have watched? Let me know which are your favorites.
Photos: Alamy
Note; this list was updated March 2025; and February 28, 2026.
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