Updated: Mar 7
I am the queen of Rom-Coms… It’s indisputable. This list will be life changing so I need you to take a deep breath and know that you will never be the same, in the best way possible.
I take this role very seriously and hope that this list will give you all the feels as these movies all hold such a special place in my heart. For the record, all my friends know that I am not one to sell them on a movie because I absolutely suck at describing them in fear of giving anything away. So, just know this list is curated with the upmost respect for your time :D.
This list is compromised of classics, heartbreak, reconciliation, adventure, life lessons, and more. This is quite literally an education in all that Rom-Com stands for. I would like to thank my mother for bestowing this intellect upon me so I can take it and bestow it on you.
Now there are some rules…
You MUST watch these movies from start to finish unless you’re not feeling it.
You HAVE to share these with your friends because these movies matter.
You NEED to figure out the take away message.
You ABSOLUTELY have to let me know which one is your favorite!
Well, I think that covers it…Without further ado, let us begin…
When Harry Met Sally (1989) Hulu, SlingTV, Fubo, Amazon Prime Video, iTunes, Showtime
We are starting with my favorite of ALL TIME. My mom introduced me to her favorite which is now mine and I am forever grateful. When Harry Met Sally is an iconic rom-com that is a screenplay by another favorite of mine, Nora Ephron. You will see that name a few times on here. GET INTO THIS MOVIE! You won’t regret it.
“In 1977, college graduates Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a contentious car ride from Chicago to New York, during which they argue about whether men and women can ever truly be strictly platonic friends. Ten years later, Harry and Sally meet again at a bookstore, and in the company of their respective best friends, Jess (Bruno Kirby) and Marie (Carrie Fisher), attempt to stay friends without sex becoming an issue between them.”
Lovebirds (2020) Netflix
I friggin’ love Issa Rae so that is reason enough to watch this, but this movie is actually really funny… In my opinion. There have been mixed reviews but I’ve seen it twice and I’ve enjoyed it both times equally.
“On the brink of breaking up, a couple gets unintentionally embroiled in a bizarre murder mystery. As they get closer to clearing their names and solving the case, they need to figure out how they, and their relationship, can survive the night.”
She’s All That (1999) Youtube, Google Play, Vudu, Amazon Prime Video, Itunes
I mean… CLASSIC 90’s movie at it’s finest. Freddie Prinze Jr. at his peak, popular highschooler falls in love with the nerd?! Yup, it’s fantastic. If you have yet to see this movie, what are you even doing with your life?! I mean seriously.
“High school hotshot Zach Siler (Freddie Prinze Jr.) is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor (Jodi Lyn O’Keefe), leaves him for sleazy reality-television star Brock Hudson (Matthew Lillard). Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs (Rachael Leigh Cook) — and help her to become the school’s next prom queen.”
Crazy Rich Asians (2018) Hulu, HBO Max, Vudu, Google Play, Sling TV, Youtube
I seriously enjoyed this movie from the storyline to the visuals. It is a gorgeous movie from a visual standpoint. Also, there will be a sequel coming out this year so be sure to watch it before that happens!
“Rachel Chu is happy to accompany her longtime boyfriend, Nick, to his best friend’s wedding in Singapore. She’s also surprised to learn that Nick’s family is extremely wealthy and he’s considered one of the country’s most eligible bachelors. Thrust into the spotlight, Rachel must now contend with jealous socialites, quirky relatives and something far, far worse — Nick’s disapproving mother.”
You’ve Got Mail (1998) Hulu, HBO Max, Youtube, iTunes, Vudu, Google Play
Insert second favorite Nora Ephron film. You’ve Got Mail is a damn classic! New York City, books, and a super sweet storyline. Yes, please. If you have yet to see this movie, I’m kind of hurt but you can change that immediately.
“Struggling boutique bookseller Kathleen Kelly (Meg Ryan) hates Joe Fox (Tom Hanks), the owner of a corporate Foxbooks chain store that just moved in across the street. When they meet online, however, they begin an intense and anonymous Internet romance, oblivious of each other’s true identity. Eventually Joe learns that the enchanting woman he’s involved with is actually his business rival. He must now struggle to reconcile his real-life dislike for her with the cyber love he’s come to feel.”
PIN ITThe Photograph (2020) Hulu, HBO Max, Youtube, Amazon Prime Video, Vudu, Google Play
Another Issa Rae film, what can I say, I’m a fan. This movie is really good, though. I didn’t really know what to expect but I definitely got sucked in and enjoyed it. It’s a great one to watch with your boo, too.
“When famed photographer Christina Eames dies unexpectedly, she leaves her estranged daughter, Mae, hurt, angry and full of questions. When Mae finds a photograph tucked away in a safe-deposit box, she soon finds herself delving into her mother’s early life — an investigation that leads to an unexpected romance with a rising journalist.”
PIN ITRunaway Bride (1999) Netflix, Amazon Prime Video, Google Play, Youtube, Vudu, iTunes
I love when movies use iconic duos and Richard Gere and Julia Roberts is no exception to that. This movie is a damn classic. You can’t be a Rom-Com fan without seeing Runaway Bride. The storyline is cute, the cast is great, the chemistry is adorable, it’s just a feel good movie you can’t ignore!
“Having already left three grooms at the altar, Maggie Carpenter (Julia Roberts) is branded “the runaway bride” by jaded city journalist Ike Graham (Richard Gere). But, after his facts are called into question, Ike races to Maggie’s hometown to save his reputation and report on her upcoming fourth trip down the aisle — during which he’s convinced she’ll run again. Though he’s there on a muckraking mission, Ike can’t help but fall for this breathtaking heartbreaker.”
Always Be My Maybe (2019) Netflix
Ok, this movie is seriously cute. Beyond it being funny and kind of having a new spin on a Rom-Com, the soundtrack is dope. If you’re a hip-hop head, you’ll seriously enjoy the music choices. Now, don’t get me wrong, this movie isn’t groundbreaking it’s just good. Plus, Keanu Reeves is in it shockingly.
“Childhood sweethearts have a falling out and don’t speak for 15 years, only reconnecting as adults when Sasha runs into Marcus in San Francisco. Although the old sparks are still there, the couple live in different worlds.”
10 Things I Hate About You (1999) Disney+, iTunes, Youtube, Google Play, Amazon Prime Video, Vudu
Ugh, Heath Ledger (RIP). This is a classic 90’s film and we’ve all seen it like 100 times but it has a place on this list because it’s so classically 90’s! Now, some of you might live under rocks which I get, it’s comfortable, so maybe this hasn’t been seen yet, so allow me to introduce you to the amazing, 10 Things I Hate About You… Enjoy! (Side note, Julia Stiles does not try to dance hip hop for more than 5 seconds in this movie, so can I get a hallelujah?).
“Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn’t attract many boys. Unfortunately for her younger sister, Bianca (Larisa Oleynik), house rules say that she can’t date until Kat has a boyfriend, so strings are pulled to set the dour damsel up for a romance. Soon Kat crosses paths with handsome new arrival Patrick Verona (Heath Ledger). Will Kat let her guard down enough to fall for the effortlessly charming Patrick?”
Sylvie’s Love (2020) Amazon Prime Video
My new favorite! This movie is a period piece set in the late 50’s in good ol’ NYC and is so good. Plus, Rege Jean Page is in it, for my Bridgerton fans. This makes you want to go find an old-school type of love and listen to jazz music. It’s so good, please go watch it. You’ll love it.
“Sylvie has a summer romance with a saxophonist who takes a summer job at her father’s record store in Harlem. When they reconnect years later, they discover that their feelings for each other have not faded with the years.”
Sixteen Candles (1984) Youtube, iTunes, Amazon Prime Video, Google Play, Vudu
You can’t have a Rom-Com list without featuring every single Molly Ringwald film, it would be criminal not to. This movie is the epitome of this list. Sixteen Candles is that classic 80’s high school love story filled with epic style, oddball humor, and classic moments of young love. You must be educated on Molly Ringwald to hang out here, it’s a new requirement, as of now.
“With the occasion all but overshadowed by her sister’s upcoming wedding, angst-ridden Samantha (Molly Ringwald) faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake (Michael Schoeffling), but worries that her chastity will be a turnoff for the popular senior. Meanwhile, Samantha must constantly rebuff the affections of nerdy Ted (Anthony Michael Hall), the only boy in the school, unfortunately, who seems to take an interest in her.”
Blended (2014) Hulu, Amazon Prime Video, Sling TV, iTunes, Google Play, Youtube
This movie is STUPID funny, and I mean stupid funny. Another iconic duo of Adam Sandler and Drew Barrymore and it’s a good one! This movie always makes me laugh, probably because I find everything funny, but it’s a feel good, easy movie to watch. Anyone else a major fan of this duo?
“Recently divorced mom Lauren (Drew Barrymore) and widowed dad Jim (Adam Sandler) let their friends push them into a blind date, which goes disastrously wrong. Unsurprisingly, neither wants to see the other ever again. However, fate intervenes when both Jim and Lauren, unbeknown to each other, purchase one-half of the same vacation package at a South African resort; they and their children are forced to share the same suite and participate in a slew of family activities together.”
My Best Friend’s Wedding (1997) Neftlix, Amazon Prime Video, Youtube, iTunes, Google Play, Vudu
Another classic Julia Roberts film, featuring Dermit Mulroney (hottie alert) and a young Cameron Diaz. This movie is another feel good movie that is just one of those movies you have to see in order to claim you’re a Rom-Com fan! If you are a fan of Runaway Bride, you’ll for sure be of fan of My Best Friend’s Wedding!
“Childhood friends Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) had a deal to marry each other if they were still single by age 28. Now, four days before her 28th birthday, O’Neil announces that he’s marrying a gorgeous 20-year-old named Kimberly (Cameron Diaz). Suddenly realizing that she’s actually in love with him, Julianne vows to stop the wedding at all costs. However, when she is appointed maid of honor, things get even more complex.”
Silver Linings Playbook (2012) Netflix, Amazon Prime Video, Youtube, Google Play, iTunes, Vudu
This movie is super cute and quirky. I’m definitely a Jennifer Lawrence fan which made me eager to see this when it came out. It has a great cast, it’s a feel good movie, and it for sure pulls on the heartstrings in cute way. The humor is great, acting is great, definitely worth seeing.
“After losing his job and wife, and spending time in a mental institution, Pat Solatano (Bradley Cooper) winds up living with his parents (Robert De Niro, Jacki Weaver). He wants to rebuild his life and reunite with his wife, but his parents would be happy if he just shared their obsession with the Philadelphia Eagles. Things get complicated when Pat meets Tiffany (Jennifer Lawrence), who offers to help him reconnect with his wife, if he will do something very important for her in exchange.”
Sex and The City: The Movie (2008) Netflix, Amazon Prime Video, Youtube, Google Play, iTunes, Vudu
This movie is another “pop culture” classic, I feel like. Now the description doesn’t do it justice. It’s hilarious, Jennifer Hudson is in it, and it’s just SEX AND THE CITY! I mean, there is no reason to not watch. My description might me worse…
“Four years after the earlier adventures of Carrie Bradshaw (Sarah Jessica Parker) and her best gal pals, she and her intermittent lover, Big (Chris Noth), are in a committed relationship. Samantha (Kim Cattrall), having survived cancer, has a monogamous relationship with Smith Jerrod. Charlotte (Kristin Davis) and her husband live on Park Avenue, and Miranda (Cynthia Nixon), now in Brooklyn, feels the pressure of family life.”
Sleepless in Seattle (1993) Hulu, Sling TV, Starz, Amazon Prime Video, iTunes, Vudu, Philo
Nora Ephron #3! Tom Hanks and Meg Ryan come together again in another absolute classic Rom-Com that gives you all the feels! Plus, the reference a classic scene from An Affair to Remember… I’ll let you guess it. Anyways, It’s fab.
“After the death of his wife, Sam Baldwin (Tom Hanks) moves to Seattle with his son, Jonah (Ross Mallinger). When Jonah calls in to a talk-radio program to find a new wife for his father, Sam grudgingly gets on the line to discuss his feelings. Annie Reed (Meg Ryan), a reporter in Baltimore, hears Sam speak and falls for him, even though she is engaged. Unsure where it will lead, she writes Sam a letter asking him to meet her at the Empire State Building on Valentine’s Day.”
The Incredible Jessica James (2017) Netflix
Not gonna lie, I have never seen this movie before, but I am changing that as I write this! So, let’s just conveniently divert our attention to this official movie synopsis right…… HERE:
“Jessica, an aspiring playwright in New York City, is trying to get over a recent break-up when she meets Boone, who’s also recovering from a recent split. Together, they figure out a way to make it in a “post-relationship” world.”
Again, not gonna lie, was expecting a longer description than that but ok!
Pretty in Pink (1986) Amazon Prime Video, iTunes, Youtube, Google Play, Vudu
Another Molly Ringwald classic. This is actually my favorite in comparison of Sixteen Candles. It’s another high school, awkward girl, type of storyline, but this is about an education in the classics that have been the drivers of this genre for decades, get my point? Anyways, go watch it and live your best 80’s life.
“Andie (Molly Ringwald) is an outcast at her Chicago high school, hanging out either with her older boss (Annie Potts), who owns the record store where she works, or her quirky classmate Duckie (Jon Cryer), who has a crush on her. When one of the rich and popular kids at school, Blane (Andrew McCarthy), asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realizes that dating someone from a different social sphere is not easy.”
The Proposal (2009) iTunes, Amazon Prime Video, Youtube, Vudu, Google Play
Let’s get one thing straight, Betty White is in this film so that should be all I have to say to encourage you to watch this movie. Betty White is queen. But, between Betty, Ryan Reynolds and Sandra Bullock, this movie is super cute and funny. I always enjoy watching it.
“Faced with deportation to her native Canada, high-powered book editor Margaret Tate (Sandra Bullock) says she’s engaged to marry Andrew Paxton (Ryan Reynolds), her hapless assistant. Andrew agrees to the charade, but imposes a few conditions of his own, including flying to Alaska to meet his eccentric family. With a suspicious immigration official always lurking nearby, Margaret and Andrew must stick to their wedding plan despite numerous mishaps.”
Moonstruck (1987) iTunes, Youtube, Google Play, Vudu
Oh, Moonstruck. What a masterpiece…Cher at her finest. My mom introduced me to this film, like most of this list, and I loved it! It’s so overtly dramatic at times in a humorous way, it’s fantastic. You can not go wrong when choosing to watch this one.
“No sooner does Italian-American widow Loretta (Cher) accept a marriage proposal from her doltish boyfriend, Johnny (Danny Aiello), than she finds herself falling for his younger brother, Ronny (Nicolas Cage). She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she’s not the only one in her family with a secret romance.”
How to Lose a Guy in 10 Days (2003) iTunes, Youtube, Google Play, Vudu
Classic, am I right?! If you say no… “bullshit” (get it?). Anyways, this movie is almost always on TV because it’s such a damn early 2000’s classic. Kate Hudson, Matthew McConaughey, I mean… it’s a no brainer.
“An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.”
The Princess Bride (1987) Disney+, iTunes, Hulu, Youtube, Amazon Prime Video
Another classic for you! This movie holds a dear place in my heart from childhood. Full of comedy, romance, and adventure you must, must, must see The Princess Bride if you were deprived of this gem. It’s on Disney+ for cryin’ out loud!
“A fairy tale adventure about a beautiful young woman and her one true love. He must find her after a long separation and save her. They must battle the evils of the mythical kingdom of Florin to be reunited with each other. Based on the William Goldman novel “The Princess Bride” which earned its own loyal audience.”
(500) Days of Summer (2009) Hulu, Starz, Sling TV, Philo, Youtube, Amazon Prime Video
Let’s add a little drama to the mix shall we? This movie, minus the adorable cast of Zooey Deschanel and Joseph Gordon-Levitt, is such a good movie. There’s some tenderness, some sweet moments, and a good storyline. It won’t disappoint.
“Tom (Joseph Gordon-Levitt), greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer (Zooey Deschanel), suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.”
Coming to America (1988) Amazon Prime Video, Youtube, Google Play, iTunes, Vudu
This honestly doesn’t even need a description. This is just one of those movies that you have to watch in order to be considered human. If you haven’t seen this movie, SHAME ON YOU! lol. It’s OK, we just need to fix this ASAP. Go watch it, you will absolutely be glad you did. Plus, the sequel is coming out soon and you don’t want to be that lame friend that has no idea what’s going on.
“Prince Akeem (Eddie Murphy) is the prince of a wealthy African country and wants for nothing, except a wife who will love him in spite of his title. To escape an arranged marriage, Akeem flees to America accompanied by his persnickety sidekick, Semmi (Arsenio Hall), to find his queen. Disguised as a foreign student working in fast food, he romances Lisa (Shari Headley), but struggles with revealing his true identity to her and his marital intentions to his king father (James Earl Jones).”
Roman Holiday (1953) Google Play, Vudu, iTunes, Pluto TV, Youtube, Amazon Prime Video
Let me introduce you to one of the original classics of the Rom-Com genre with none other than Roman Holiday, featuring Audrey Hepburn. This is one of those movies that paved the way for so many others. You can’t be a Rom-Com fanatic without having Roman Holiday in your repertoire.
“Overwhelmed by her suffocating schedule, touring European princess Ann (Audrey Hepburn) takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls asleep on a park bench and is found by an American reporter, Joe Bradley (Gregory Peck),who takes her back to his apartment for safety. At work the next morning, Joe finds out Ann’s regal identity and bets his editor he can get exclusive interview with her, but romance soon gets in the way.”
Serendipity (2001) Amazon Prime Video, iTunes, Youtube, Vudu, Pluto TV
I stumbled across this gem in high school and watched it once a week every week for like two months. I don’t know why… Maybe because it’s set in New York City, but I love this one. It’s a sweet story, tugs at your heart, and is a little whimsical too. You’ll enjoy it, promise.
“On a magical night when they are in their 20s, Jonathan (John Cusack) meets Sara (Kate Beckinsale). He finds it love at first sight, but Sara believes in destiny. After 10 years the two — with 3,000 miles between them — must decide if fate wants them to be together again. When love feels like magic, it is called destiny; when destiny has a sense of humor, it is serendipity.”
The Wedding Date (2004) Hulu, HBO Max, Amazon Prime Video, iTunes, Youtube, Google Play
I don’t know what it is about Dermot Mulroney that I find attractive, but here we are. Great cast, amazing setting, cute story, and lots of humor. It’s a keeper in my book and one I frequently watch when I need a smile. Highly recommend.
“With the wedding of her younger sister (Amy Adams) fast approaching, Kat Ellis (Debra Messing) faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey (Jeremy Sheffield), the man who left her as they moved closer to marriage, happens to be the groom’s best man. Determined to show everyone — most of all Jeffrey — that her romantic life is as full and thrilling as ever, Kat hires a charming male escort (Dermot Mulroney) as her date.”
While You Were Sleeping (1995) Disney+, iTunes, Youtube, Google Play, Vudu, Amazon Prime Video
Gah! Another one that holds a dear place in my heart. This is a great one to watch around the holiday’s but we got a ways until then so watch it now, right now. It’s just so cute.
“Lonely transit worker Lucy Eleanor Moderatz (Sandra Bullock) pulls her longtime crush, Peter (Peter Gallagher), from the path of an oncoming train. At the hospital, doctors report that he’s in a coma, and a misplaced comment from Lucy causes Peter’s family to assume that she is his fiancée. When Lucy doesn’t correct them, they take her into their home and confidence. Things get even more complicated when she finds herself falling for Peter’s sheepish brother, Jack (Bill Pullman).”
Pretty Woman (1990) iTunes, Youtube, Google Play, Vudu, Amazon Prime Video
Okay, obviously this one had to make the list. Again Julia Roberts and Richard Gere… Here for it. But, They had this playing on repeat in the hospital after delivering Shay so now I kinda dislike it because that was a painful time lol, but nonetheless, this is a must watch.
“In this modern update on Cinderella, a prostitute and a wealthy businessman fall hard for one another, forming an unlikely pair. While on a business trip in L.A., Edward (Richard Gere), who makes a living buying and breaking up companies, picks up a hooker, Vivian (Julia Roberts), on a lark. After Edward hires Vivian to stay with him for the weekend, the two get closer, only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.”
50 First Dates (2004) Netflix, Hulu, Sling TV, fuboTV, Vudu, Amazon Prime Video
Another Drew Barrymore/Adam Sandler goodie. I know we all have seen this, but in the rare chance that maybe you haven’t, here ya go! Just a true golden icon of Rom-Com goodness + weirdness from Adam Sandler!
“Playboy vet Henry sets his heart on romancing Lucy, but she has short-term memory loss; she can’t remember anything that happened the day before. So every morning, Henry has to woo her again. Her friends and family are very protective, and Henry must convince them that he’s in it for love.”
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