Originally posted on Love, Geeky Girl

By: Dani Kessel

I have the biggest love affair with romantic comedy movies. People hate the genre, but I enjoy it so much that I took a film class during university centered on deconstructing, analyzing, and tracking the progression of rom-coms from the 1930s to now and projecting into the future. We were tasked with learning the different subgenres and tropes. Then, we put all of this to use in studying almost two dozen different films. Watching those movies was some of the best fun I had the whole 5 years I was in college. I’ve seen some of the best and worst in the genre.

If you are looking for some great romantic comedy movie options for your next date night, cuddle up and put on one of these entertaining flicks.

1. It Happened One Night (1934) – Unrated

  • Available on Hulu with Live TV, Sling TV, fuboTV, and Crackle

When a rich socialite named Ellie Andrews runs away from her controlling father and her new husband, she becomes entangled with a newspaper reporter named Peter Warne on her escapist journey. This film set the tone and zaniness for all screwball rom-coms over the years.

2. When Harry Met Sally (1989) – R

  • Available on Hulu

Harry and Sally take a tense road trip together from Chicago to NYC in which they bicker about whether men and women can be friends. Ten years later, they meet again. They decide to put it to the test whether they can stay friends without sex getting in the way.

3. How to Lose a Guy in 10 Days (2003) – PG13

  • Available on Hulu with HBO add-on

Advice columnist, Andie, gets assigned an article in which she has to do everything she can to get a guy to leave her in 10 days. Advertiser, Benjamin, makes a bet with his coworkers and boss that she can get him to fall in love with her in 10 days. They meet in a bar, each with their own agendas, and engage in a tumultuous and hilarious relationship.

4. Sleeping With Other People (2015) – R

  • Available on Netflix

After a one night stand in college, Lainey and Jake meet again twelve years later at a sex addicts meeting. Lainey is a love addict who engages in a toxic relationship with her old college TA. Jake is a serial cheater who can’t hold down a relationship. After one date, they decide it best to be friends. But, will their sexual tension get in the way?

5. Lez Bomb (2018) – Unrated

  • Available on Netflix

Lauren’s going home to her family for thanksgiving and decides to bring her girlfriend Hailey. Only one problem. Lauren isn’t out to her family as a lesbian. Her family holiday goes awry when Lauren’s roommate Austin shows up unexpectedly, making her family think he and Lauren are together.

6. America’s Sweethearts (2001) – PG13

  • Available on Hulu with STARZ add-on

Movie stars Gwen and Eddie are estranged husband and wife. When they are forced to do one last press junket together, Eddie and Gwen are hostile towards each other. In order to decrease problems, Gwen’s sister/personal assistant becomes the go-between. But things go sideways when Eddie and Kiki find themselves developing romantic feelings for each other.

7. Love, Simon (2018) – R

  • Not currently available for free online streaming. Rumored to be available on Hulu soon.

Simon wants nothing more than to find his love story. But when 17-year-old Simon Spier finds himself falling for an online classmate, he grapples with both coming-out as gay and trying to find out who his anonymous love-interest is. Will Simon ever meet his mystery man? This movie exudes John Hughes vibes as Simon finds himself in an adorable rom-com.

8. Groundhog Day (1993) – PG

  • Available on Hulu with SHOWTIME add-on

Weatherman and reporter, Phil Connors, finds himself in a repeating loop of Groundhog Day. Once he discovers his predicament, he uses the situation to his advantage and attempts to cover the day’s events and woo his crush, Rita. This is my partner’s favorite rom-com, though he is also a rom-com lover. In my experience, even people who hate rom-coms love this movie! 

9. Always Be My Maybe (2019) – PG13

  • Available on Netflix

Childhood sweethearts, Sasha and Marcus, have a falling out which results in them not speaking for 15 years. When they run into each other again, they begin to consider whether they should become romantically involved despite living in two entirely different worlds.

10. Two Night Stand (2014) – R

  • Available on Tubi and Vudu

Two people find themselves stuck together for a second day and night when a snowstorm hits post-hook-up. They take advantage of this situation by getting to know each other better and teaching each other how to be better sex-partners.

11. Duck Butter (2018) – Unrated, Explicit

  • Available on Netflix

After nasty breakups, Naima and Sergio meet each other at the club. They decide to see if they can create intimacy by having sex every single hour for 24 hours. But will the experiment result in romance for these two women?

12. My Best Friend’s Wedding (1997) – PG13

  • Available on Crackle

Julianne and Michael made an agreement that they would get married at 28 if they were still single. A few days before Julianne’s 28th birthday, she gets a call from Michael announcing that he is getting married. As she arrives for the wedding she discovers that she’s in love with Michael, gets appointed maid-of-honor, and vows to stop the wedding. 

13. Love & Basketball (2000) – PG13

  • Not available for free online streaming

Childhood best friends, Monica and Quincy, both aspire to be basketball stars. When they start falling for each other, they get their own big breaks pulling them apart. They come back together as Quincy gets engaged. Will he marry someone else or will they be able to come back together? The movie explores the dichotomy of passion versus romance.

14. The Thing About Harry (2020) – Unrated

  • Available on Hulu and Sling TV

Sam, a young gay man, is forced to share a car ride with his childhood bully, Harry. When Harry comes out to Sam as pansexual, a budding romance develops. The plot follows Sam and Harry’s dynamic over the next few years as they navigate friendship and attraction. This movie pays homage to When Harry Met Sally.

15. Love Actually (2003) – R

  • Available on Hulu with HBO add-on

Nine love stories with different paths intertwine over the Christmas season.

16. Isn’t It Romantic? (2019) – PG13

  • Available on Hulu with HBO add-on and HBO Now

Natalie is cynical about love and desperate to get recognized at her work. When Natalie gets knocked unconscious, she wakes up to find herself in an alternate version of her life where she’s the leading lady in a rom-com story.

17. Friends With Benefits (2011) – R

  • Available on Hulu with STARZ add-on

Work colleagues Jamie and Dylan become close friends. After many failed relationships, they decide to start up a friend-with-benefits relationship with each other. Over time, they find themselves developing feelings for each other though.

18. Man Up (2015) – R

  • Available on Netflix

While traveling across London, Nancy accidentally hijacks Jack’s blind date. Nancy decides to go along with this, pretending to be his date, Jessica. As they develop romantic chemistry, Nancy struggles with how to tell Jack that she’s not who he thinks she is.

19. Some Kind of Wonderful (1987) – PG13

  • Available on Hulu

Blue-collar Keith lands a date with popular-girl Amanda. In order to impress Amanda, Keith recruits his tomboy friend Watts to act as their driver for the night. What Keith doesn’t know is that Watts is in love with him.

20. What’s Your Number? (2011) – R

  • Available on Hulu with CINEMAX add-on

When Ally Darling gets fired and dumped, she reads an eye-opening magazine article that women who’ve been sexual with more than 20 people aren’t likely to get married. The problem is that she’s already hit 20. She enlists the help of her promiscuous neighbor, Collin, to track down her old ex-boyfriends in hopes that one of them is her soulmate.

Those are my top picks for date night rom-coms. In the list, I tried to include a nice variety of subgenres with diversity in the casts. I added the ratings too so that you could choose whatever is most comfortable for you. There’s something for everyone!

So, tell me, which one are you going to watch? What’s your favorite rom-com? Are there any ones I’m missing that you’d add to the list? Let me know in the comments below.

Visit LoveGeekyGirl.com for more great content!

3 thoughts on “20 Great Rom-Com Movies for Date Night

  1. Well I also love this genre! You had a couple good ones I liked and some I didn’t know…

    I love the movie “Never Been Kissed” with Drew Barrymore

    And “13 going on 30”

    Those are the 2 favorites that come to mind off the top of my head ✌️

    Like

      1. Yes I love her too!

        I used to love Adam Sandler lol… until he did the movie “Click” …can’t really forgive him for making me cry so much in one movie lol …

        … and he always has the same kinda guy/character… but he sticks to his classic – I guess I will give him props for that.

        I remembered the name but had to look it up to remember the movie itself … yeah that’s a funny one! Blended. I remember that lol – that is a good one.

        They do a lot of movies together lol

        Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s