Romantic Comedy Movies to Watch in Your 20s

Romantic Comedy Movies to Watch in Your 20s

I love romantic comedy movies because they’re not all sappy and emotional. You get to entertain yourself with their funny lines, and they’re relatable 99.9% of the time.

That’s exactly why I turn to romantic comedy movies for an instant mood booster when nothing else works anymore. We all need a good laugh at the end of a bad day.

So if you’re having one of those off days, I’ve picked a few of my favorite romantic comedy movies of all time. The good news is that they’re all on Amazon Prime.

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What’s Your Number (2011)

A woman looks back at the past nineteen men she’s had relationships with in her life and wonders if one of them might be her one true love. (IMDB)

I swear I can watch this movie over and over again. It’s fun to watch because it’s REALLY hilarious, with the right amount of romance. Both lead characters are totally relatable. Anna Farris and Chris Evans really have this cute chemistry, and I specifically love the basketball scene. Chris Pratt’s multiple appearances also added to the comedy! You WOULD want to see two Chrises in a rom-com movie. PS: brace yourself for unnecessary food cravings while watching this.

Watch on Amazon Prime.

Sleeping with Other People (2015)

A good-natured womanizer and a serial cheater form a platonic relationship that helps reform them in ways, while a mutual attraction sets in. (IMDB)

I’m not sure if you’re going to like this as I did. You’d think that it somehow revolved around sex, making you question the concept of love, or if everything’s about lust when dating in your 20s. It’s kind of like What’s your number, but the lines are deeper. I did love it because I think it’s realistic that people have emotional baggage nowadays. The important thing is to find someone with who you can be comfortable with.

Watch on Amazon Prime.

Love, Rosie (2014)

Rosie and Alex have been best friends since they were 5, so they couldn’t possibly be right for one another…or could they? When it comes to love, life, and making the right choices, these two are their own worst enemies. (IMDB)

Love Rosie can be very frustrating, and somehow… unrealistic. It has a lot of cliches, but Lily Collins and Sam Claflin’s pair was amazing. I guess what I really loved about it is that it gives this lesson that one should not waste time hiding your feelings towards someone. There’s no need to hold it in, don’t be like Alex and Rosie. 😉 If you’re in love with a best friend from the opposite sex, this movie is a must-watch.

Watch on Amazon Prime.

Date Night (2010)

In New York City, a case of mistaken identity turns a bored married couple’s attempt at a glamorous and romantic evening into something more thrilling and dangerous. (IMDB)

If you’ve watched Walk of shame, Date Night is kind of like that. The only difference is that this time, the couple gets involved in a series of unfortunate and thrilling adventures. It’s a bit frustrating to watch them go through every unlucky encounter, but it’s definitely funny. Tina Fey and Steve Carell together? Come on, who wouldn’t enjoy it?

Watch on Amazon Prime.

The Proposal (2009)

Romantic comedy movies - The Proposal

A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada. (IMDB)

It may be the typical boss-assistant love story, but the scenes will crack you up big time. Albeit the serious type, Sandra Bullock was effortlessly funny. Ryan Reynolds is also one of my favorite rom-com actors because he looks like this innocent, good guy who hides all his feelings but loves you anyway. You’d also want to go to Alaska after watching this.

Watch on Amazon Prime.

Definitely, Maybe (2008)

A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter. (IMDB)

Definitely, Maybe honestly reminded me of the series How I met your mother, with somehow the same ending. I absolutely love the storytelling and the casting. For me, the three girls also represent the three loves we have in a lifetime—the best friend, the sweetheart, and the one who betrays us. It’s perfect if you want a funny movie with more romance.

Watch on Amazon Prime.

The Ugly Truth (2009)

An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man. (IMDB)

I’ve seen a lot of reviews about this movie being sexist and cliche, but to be honest it’s a realistic film that we can easily relate to nowadays. You’ll love how it can be painfully honest, hence it’s called the ugly truth. I really love Katherine Heigl. She plays the same character of a classy, control freak girl that I really adore. I kept looking at Gerard Butler as the 300’s King of Sparta though.

Watch on Amazon Prime.

Killers (2010)

A vacationing woman meets her ideal man, leading to a swift marriage. Back at home, however, their idyllic life is upset when they discover their neighbors could be assassins who have been contracted to kill the couple.. (IMDB)

I honestly didn’t expect the chemistry between Ashton Kutcher and Katherine Heigl, but it worked pretty okay. Lower your expectations, though, as it’s not your happy rom-com where you’ll constantly laugh at the dialog. I was more entertained by their acting.

Watch on Amazon Prime.

Life as We Know It (2010)

Two single adults become caregivers to an orphaned girl when their mutual best friends die in an accident. (IMDB)

Life as we know it is probably the best Katherine Heigl I’ve ever seen. Her acting really matched the film. This movie will make you laugh and cry, I swear. It was a total roller coaster ride that allows you to peek into the good and the bad times of life. It also shows the value of friendship.

Watch on Amazon Prime.

When in Rome (2010)

Beth is a young, ambitious New Yorker who is completely unlucky in love. However, on a whirlwind trip to Rome, she impulsively steals some coins from a reputed fountain of love and is then aggressively pursued by a band of suitors. (IMDB)

When in Rome is not your typical rom-com movie, because it’s literally magical. It’s one of the movies I recommend for a feel-good, without any stress building up at all. Just like in Life as we know it, Josh Duhamel was great in here. Kristen Bell IS gorgeous.

Watch on Amazon Prime.

Happy watching! Don’t forget to comment below if you have any suggestions for romantic comedy movies.

Here are other films/TV series roundups you might like:

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