The Best Romantic Comedies To Watch On HBO Max Right Now

Toula and Ian in My Big Fat Greek Wedding.
(Image credit: IFC Films)

Few film fans can deny that any time is a good time to curl up on the couch with your favorite snacks and enjoy a movie marathon of any genre. But, if you want to come away from your movie night with lots of warm and fuzzy feels, we all know that one of the best options is to dive right in by streaming some of the best romantic comedies currently on offer. 

If this is what you’re currently after, or anticipate such a desire coming along soon, we have an awesome list of great rom-coms that are streaming right now, and can be delighted in as long as you have an HBO Max subscription. OK, let the rom-com love begin!

Constance Wu in Crazy Rich Asians

(Image credit: Warner Bros. Pictures)

Crazy Rich Asians (2018)

This great romantic comedy is one to make you smile. Crazy Rich Asians, starring Constance Wu and Henry Golding, follows a couple that travels to Singapore, only for the girlfriend to find out that her fiancé's side of the family is insanely rich. Now, she has to find a way to fit in and impress his family. 

I could say a lot about this movie, but I think everyone should watch it at least once without spoilers. The Crazy Rich Asians cast is great, and there’s a lot of cool behind the scenes stuff too you should know once you watch it. Such a heartwarming film. 

Stream Crazy Rich Asians on HBO Max.

Meg Ryan and Tom Hanks in Sleepless in Seattle

(Image credit: TriStar Pictures)

Sleepless In Seattle (1993)

This Nora Ephron-directed gem is definitely famous for a reason. The story follows the unlikely long-distance romance of engaged Annie (Meg Ryan) and recently widowed Sam (Tom Hanks), which is significantly helped along by Sam’s determined son, Jonah (Ross Malinger).

Most rom-com conversations are nothing without at least a mention of this summer hit, which has a number of memorable scenes to go along with its funny, heartwarming story. Be sure to check out the fascinating Sleepless in Seattle behind–the–scenes facts after you watch!

Stream Sleepless in Seattle on HBO Max. 

Steve Carell and Ryan Gosling in Crazy Stupid Love

(Image credit: Warner Bros.)

Crazy Stupid Love (2011)

If you’re looking for a great romantic comedy that has an awesome ensemble, then you need to check out Crazy Stupid Love. This film follows a man who is in the state of a marriage that is falling apart, so in order to make himself feel better, he tries to pick up women at bars – and fails miserably. A womanizer takes pity on him and decides to teach him to actually pick up women. –. 

This film is honestly one of the better romantic comedies that I’ve seen in years just because the Crazy Stupid Love cast has such good chemistry with each other, but what really makes it better than most is the acting. You have the amazing Steve Carell, Ryan Gosling, Emma Stone and more. It’s truly a standout movie. 

Stream Crazy Stupid Love on HBO Max.

ricki lake and brendan fraser in mrs. winderbourne

(Image credit: TriStar Pictures)

Mrs. Winterbourne (1996)

You may not have heard of Mrs. Winterbourne, but it features one of the more intriguing rom-com set ups involving mistaken identity. When the pregnant and penniless Connie (Ricki Lake) boards a train to get out of the rain, she meets newlywed Hugh Winterbourne (Brendan Fraser) and his pregnant wife. After a horrible accident, though, Connie finds herself being mistaken for Hugh’s wife and is taken in by his rich mother, Grace (Shirley MacLaine), and his doubtful identical twin brother, Bill (also a delightful Brendan Fraser).

This movie is an unexpected delight for those who like enemies-to-lovers romances, and it features some LGBTQ+ representation, as well.

Stream Mrs. Winterbourne on HBO Max.

hugh grant and sandra bullock in two weeks notice

(Image credit: Warner Bros. Pictures)

Two Weeks Notice (2002)

Sandra Bullock stars as lawyer and activist Lucy, who takes a job as chief counsel to billionaire real estate developer George (Hugh Grant). But, he’s also slept with nearly all of Lucy’s predecessors, and while the two have a decent (and non-sexual) working relationship, the pressures of the gig become too much, prompting Lucy to give notice that she’s quitting, leading both of them to realize that there might be something more between them.

It would seem that you can’t go wrong when you combine the rom-com forces of Bullock and Grant, as was done in this film. Two Weeks Notice offers viewers a light and funny slow burn romance that is very much propelled forward by the undeniable charm of its stars.

Stream Two Weeks Notice on HBO Max. 

Gloria Estefan and in Father of the Bride.

(Image credit: Warner Bros./HBO Max)

Father Of The Bride (2022)

In this remake of the classic comedies released in 1950 and 1991, Father of the Bride stars Andy Garcia and Gloria Estefan as two parents who are going through a divorce, but when their children come home, one of them announces that she intends to marry her fiance in one month. For the sake of their children, they put it to the side to be there for her, but life turns upside down in many different ways. 

Honestly, I actually like this remake more than the 1991 version. Not only does it feature a stellar cast, but the jokes just feel like they land better. I do love Steve Martin in the first remake’s lead role but Andy Garcia rocked it too – and Gloria Estefan is always a win. This HBO Max original is worth the time. 

Stream Father of the Bride on HBO Max. 

Tom Hanks and Meg Ryan in You've Got Mail

(Image credit: Warner Bros.)

You’ve Got Mail (1998)

Want to talk about a classic rom-com, check out You’ve Got Mail. This movie is another good enemies to lovers classic of two rival business owners who end up connecting over the littlest thing - through instant messaging. 

It’s certainly one of the best Meg Ryan movies, but Tom Hanks is awesome in this as well. Give it a watch if you haven’t seen it yet. 

Stream You’ve Got Mail on HBO Max. 

Meg Ryan and Billy Crystal in When Harry Met Sally

(Image credit: Columbia Pictures)

When Harry Met Sally (1989)

Chance encounters are rare, which is what makes When Harry Met Sally so great following several moments in their lives that define their relationship. 

I mean, we all know that one diner scene from the movie, but I promise the rest of the film is awesome as well and so funny, especially starring Billy Crystal and Meg Ryan. Thank God it didn’t have a depressing ending.

Stream When Harry Met Sally on HBO Max.

Adam Sandler and Drew Barrymore in The Wedding Singer

(Image credit: New Line Cinema)

The Wedding Singer (1998)

In this classic Adam Sandler movie, The Wedding Singer is about a man (Adam Sandler) who works as a wedding singer, but his life changes when he’s broken up with by his girlfriend, and he ends up falling for a nice woman (Drew Barrymore) who is getting married to the wrong guy. Now, he must find a way to show his love. 

Who isn’t a fan of seeing Sandler and Drew Barrymore unite on a movie screen together? These two are pure movie magic and you can’t convince me otherwise. You just have to love them. 

Stream The Wedding Singer on HBO Max.

Rachael Leigh Cook in She's All That.

(Image credit: Miramax Films)

She’s All That (1999)

You really can't do a more classic romantic comedy than She’s All That starring Rachael Leigh Cook and Freddie Prinze Jr. When Zack is broken up with by his girlfriend, his friends make a bet with him that he could make any girl the most popular girl in school in six weeks, and his friends choose Laney Boggs, one of the most unpopular girls in school. But what he doesn’t count on is falling for her. 

A modern adaptation of Pygmalion and My Fair Lady by George Bernard Shaw and George Cukor, this is probably one of the most well known teen films for a reason and it’s so funny. There was even a remake years later on Netflix called He’s All That – but respectfully, this one is much better.

Stream She’s All That on HBO Max.  

The main cast of My Big, Fat, Greek, Wedding.

(Image credit: IFC Films)

My Big, Fat, Greek Wedding (2002)

Next up, we have My Big, Fat, Greek Wedding. Starring Nia Vardalos and John Corbett, this movie follows a young Greek-American woman who falls in love with a man. The only issue is that he’s not Greek, which causes plenty of issues for her and her messy, crazy family. 

It’s certainly a memorable title, and once you watch the movie, you can see why it would be called that, as it’s hilarious. What makes it even more special is that Nia Vardalos actually wrote it based on her own experiences, so you know it’s extra awesome and funny. 

Stream My Big, Fat, Greek Wedding on HBO Max. 

robin givens and eddie murphy in boomerang

(Image credit: Paramount Pictures)

Boomerang (1992)

There’s nothing like an Eddie Murphy movie, and the same can be said for this rom-com. The story sees Murphy’s successful ad exec, Marcus, come to terms with his status as a very non-committal dater after he begins seeing Jacqueline (Robin Givens), who is essentially a female version of himself, right as he also starts to fall for the much sweeter Angela (Halle Berry).

It’s always good to watch characters learn some important lessons about love, but even better when it can be done with the kind of humor imparted by Boomerang. Plus, if you watch this one you’ll be looking at one of the best Halle Berry movies from when the rising star was still just getting started.

Stream Boomerang on HBO Max.

Vince Vaughn and Owen Wilson in Wedding Crashers.

(Image credit: New Line Cinema)

Wedding Crashers (2005)

Wedding Crashers is a hysterical comedy following two men who blatantly crash weddings to pick up women. But one of these crashes ends up taking a turn, and their whole scheme starts to become undone. 

Both Vince Vaughn and Owen Wilson are complete gems in this movie and deserve all the praise in the world. There’s a lot of behind-the-scenes facts about the movie so be sure to check those out once you watch them. 

Stream Wedding Crashers on HBO Max.

jennifer lopez ralph finnes maid in manhattan

(Image credit: Columbia Pictures)

Maid In Manhattan (2002)

Arguably one of Jennifer Lopez’s best romantic comedies to date, Maid in Manhattan is the story of a young woman working as a maid in a high-profile hotel in order to provide for her son, when one day she ends up meeting a big-time politician, and her life changes forever. 

There’s plenty of reasons to give this movie a chance. You have Jennifer Lopez in her prime of romantic comedies, as well as Ralph Fiennes before Harry Potter. You also have a cute love story in New York City. What else is there not to love?

Stream Maid in Manhattan on HBO Max. 

kate winslet in the holiday

(Image credit: Columbia Pictures)

The Holiday (2006)

Nancy Meyers is another behind–the–scenes rom-com queen, and the writer/director hit pay dirt here. The Holiday focuses on unlucky in love Englishwoman Iris (Kate Winslet, in one of her best movies) and similarly afflicted Los Angeles movie trailer producer Amanda (Cameron Diaz) switching homes for the holidays to get away from their troubles for a couple of weeks, during which time they each find solutions to their romantic problems.

In a rarity, this film gives us two romances to root for, while we also get to enjoy home design porn as only Meyers can deliver it.

Stream The Holiday on HBO Max.

uma thurman and janeane garofalo in the truth about cats & dogs

(Image credit: 20th Century Fox)

The Truth About Cats & Dogs (1996)

I happen to think this movie is one of the forgotten treasures of ‘90s rom-coms, despite it getting solid reviews when it was released. As a reinterpretation of Cyrano de Bergerac, and follows as insecure radio host Abby (Janeane Garofalo) convinces her model neighbor and friend, Noelle (Uma Thurman), to pose as Abby when handsome photographer Brian (Ben Chaplin) shows interest in her.

Look, we’ve gotten more than a few versions of this type of story, but aside from the fact that The Truth About Cats & Dogs puts the female characters front and center, it’s also a sweet, delightfully funny story that will have you rooting for Abby and Noelle, even when things get tense between the two.

Stream The Truth About Cats & Dogs on HBO Max. 

Mila Kunis and Justin Timberlake in Friends with Benefits.

(Image credit: Sony Pictures)

Friends With Benefits (2011)

Starring Justin Timberlake and Mila Kunis, Friends with Benefits is exactly as the title says – two friends who decide to start having sex with the other without becoming a couple. But obviously, things don’t go as planned, and doing this only complicates things further. 

I feel like I probably don’t need to go into why this is a funny romantic comedy. The film itself has two stars that have fun chemistry together and the premise is a tale as old as time. You really can’t get better than two friends who are just starting to get to know each other that way. 

Stream Friends with Benefits on HBO Max. 

I know there are a lot of movies on this list, which might make it hard to pick just one, but would you really have it any other way? You now have many very good options for your rom-com movie night (or morning…or afternoon) and can stream to your heart’s content (or until you start to fall asleep)...happy binging!

Alexandra Ramos
Content Producer

A self-proclaimed nerd and lover of Game of Thrones/A Song of Ice and Fire, Alexandra Ramos is a Content Producer at CinemaBlend. She first started off working in December 2020 as a Freelance Writer after graduating from the Pennsylvania State University with a degree in Journalism and a minor in English. She primarily works in features for movies, TV, and sometimes video games. (Please don't debate her on The Last of Us 2, it was amazing!) She is also the main person who runs both our daily newsletter, The CinemaBlend Daily, and our ReelBlend newsletter.