The 10 Best Funny Comedy Movies To Watch With Your Boyfriend
Finding that perfect comedy flick that you and your boyfriend will both enjoy can be a bit tricky, especially if he’s not really into those rom-coms for couples – or if you aren’t, for that matter. If you want to find something that you’ll both enjoy and share a few laughs, you’re in the perfect place. Here are the ten best, funniest comedy movies to watch with your boyfriend/girlfriend.
Honorable mention: ‘Neighbors’ (2014)
IMDb score: 6.3/10
What it’s about: A couple with a newborn child is forced to live next to a fraternity house that throws wild parties almost every day. They decide it’s time for war – so they plot to do everything they can to get the frat boys out of the house next door – even if it means getting close and partying hard first…
Why you should watch it: My girlfriend (now fiancee) moved into a new place together just recently, and we always joked about how scary it is because, even if the place itself is perfect, you never know what kind of weirdos your neighbors may be. This is the perfect movie for couples who are moving in together and have a relaxed sense of humor. If you and your man fit this bill, then this film is absolutely for you!
10. ‘The Ugly Truth’ (2009)
IMDb score: 6.4/10
What it’s about: Abby, an uptight, romantic morning show producer, struggles to find true love as she takes on a segment of the show about modern relationships. That segment, however, is hosted by a chauvinistic, misogynistic guy who conducts a series of tests in experiments involving Abby to prove to her his own romantic views.
Why you should watch it: This is one of the most classic, cookie-cutter rom-com, but it just goes to show that you can find love anywhere. No matter how different two souls might be – they might fill in the gaps of one another to form a perfect, unassuming match, and that’s how ‘The Ugly Truth’ feels.
9. ‘How to Lose a Guy in 10 Days’ (2003)
IMDb score: 6.5/10
What it’s about: Benjamin Barry is a ladies’ man who works for a large advertising company. A big client is tossed around the marketing agent, so he makes a bet with the other guys – he can make any woman fall in love with him in ten days. If he wins, he gets the client. Meanwhile, Andie is writing a story on how to ditch a guy in ten days as a bet with her boss. If she wins, she gets to write a deeper, more meaningful story. Naturally, they stumble upon each other for their ploys. Of course, it is to expect that fate will put them together for their respective tents. The question is, can love blossom even though both of them have a hidden agenda?
Why you should watch it: Another classic rom-com, but this one is just a classic. It was a ton of humor, and a couple of small life lessons here and there, but the best part is that it is absolutely fun. Like, it frustrates you at times, being the only one ‘in the room’ with all the information, but it’s a hilarious film worth a watch with your boyfriend/girlfriend.
8. ‘Game Night’ (2018)
IMDb score: 6.9/10
What it’s about: A group of middle-aged friends is obsessed with their game night traditions. However, what was supposed to be a nice, quiet game night turns into a real mystery that forces them to take the game a LOT more seriously…
Why you should watch it: I don’t think that over the last decade or so – there have been many comedies for couples that I actually, genuinely enjoyed. However, ‘Game Night’ was a breath of fresh air. There was action, a ton of humor, and even some blood (don’t worry, nothing too graphic).
The storyline is original, and I absolutely bet you’ll enjoy it. Also, if you’re a couple like myself and my woman and just utterly adore board games and game nights, this couldn’t be more perfect.
7. ‘Pretty Woman’ (1990)
IMDb score: 7.1/10
What it’s about: A wealthy businessman meets a young prostitute on the street and hires her to play the role of his date/escort to a couple of high-end social events. She agrees reluctantly, but what ends up happening is something they couldn’t have anticipated. Despite their diametrically opposite lives and backgrounds – love finds them…
Why you should watch it: ‘Pretty Woman’ is literally a classic that so many folks repeatedly watch, which is why it found its way onto the list. It’s perfect for couples because it’s funny but also smart, and shows how love works in mysterious ways and connects even the unlikeliest souls.
6. ‘The 40-Year-Old Virgin’ (2005)
IMDb score: 7.1/10
What it’s about: Andy, a 40-year-old virgin, is goaded and pressured by his buddies to finally seal the deal and find a partner. He does his best to up his game, and when he meets a sweet single mother, he feels the pressure overboiling as he tries to seduce her into bed… What he ends up getting is far, far better.
Why you should watch it: You know, the waxing scene is actually Steve Carell getting the wax depilation treatment. Those screams of pain were 100% real! It’s just a spectacularly hilarious movie that you’ll love to watch over and over again, but there is just enough romance in there for you to feel endearing and enamored if you watch as a couple.
5. ‘Jerry Maguire’ (1996)
IMDb score: 7.3/10
What it’s about: Jerry Maguire works as a sports agent – a very successful one, that is – but in order to be the best in the business, sometimes, you have to ‘trump’ your morals aside. So, when Jerry has a moral epiphany, he gets fired, so now he is trying to remake a name for himself with only a single client left by his side…
Why you should watch it: ‘SHOW ME THE MONEY!’ This is a movie about sports, so your boyfriend will likely enjoy it more than the classic rom-com. It has just enough humor and just enough of a deeper storyline that makes the film so interesting. Naturally, the pairing of talented actors such as Tom Cruise and Cuba Gooding Jr. worked well, so I highly recommend this film.
4. ’10 Things I Hate About You’ (1999)
IMDb score: 7.3/10
What it’s about: Cameron wants to date Bianca, but Bianca is forbidden from having a boyfriend until her older sister, Kat, starts dating. However, Kat is completely anti-social and doesn’t even think of relationships. Cameron gets an idea to pay a mysterious but charming boy, Patrick, to try and seduce Kat so that he can finally have Bianca…
Why you should watch it: This is one of the first roles where I’ve seen young Heath Ledger, but despite the fact that it came in a romantic comedy, I loved his performance. It was a simple but solid script, and now, 15-ish years later, the movie still stands as a great choice for a lazy Saturday night at home with popcorn, a few bears, and some snuggles.
3. ‘Crazy, Stupid, Love.’ (2011)
IMDb score: 7.4/10
What it’s about: Love works in mysterious, crazy, stupid ways. In this movie, a middle-aged man’s life is blown into pieces when his wife suddenly asks for a divorce. He wants to get back into the dating game, but after being married for so long, his ‘game’ is non-existent. Luckily, he meets a charming playboy in a bar, who teaches him how to pick up ladies efficiently.
Little did he know, those very same methods would be used against the one person he loves the most…
Why you should watch it: ‘Crazy, Stupid, Love.’ is just a hilarious movie that is well worth your time. You will laugh as hard as you ever did, but the best part of the film, I believe, is the star-studded cast that delivered a uniquely awesome performance overall – Steve Carell, Ryan Gosling, Juliane Moore, Emma Stone, Kevin Bacon, and Marisa Tomei.
2. ‘Palm Springs’ (2020)
IMDb score: 7.4/10
What it’s about: A woman wakes up on the day of a wedding that she is a guest on. Some weird stuff happens, and when she wakes up the next day – she wakes up on the day of the wedding once again. She freaks out, only to realize that there is another guest sharing the same predicament. Their romance blossoms as they try to find a way out of the time loop they’re in…
Why you should watch it: This movie is a bit more quirky, offbeat, and just overall different from the rest of the movie. Despite it being a comedy and having some romantic elements to it, what I love the most about ‘Palm Springs’ is that element of mystery and fantasy making you wonder – what in the world is actually going on here? Plus, the amazing chemistry between Andy Samberg and Cristin Milioti is palpable!
1. ‘The Hangover’ (2009)
IMDb score: 7.7/10
What it’s about: Four friends take a trip to Las Vegas as part of a bachelor party. They wake up in a trashed hotel room with no memory of what happened last night, a tiger in their bathroom, and one of their friends – the groom-to-be – missing. They’re trying to piece together their night to find Doug, but it might be more difficult and messed up than they ever thought.
Why you should watch it: Last but not least, the holy grail of comedies – ‘The Hangover’ is a movie your boyfriend will absolutely, unequivocally love, and so will you. Why? Because it’s just hilarious, and the hype is real. The sequel and threequel are also great, but the first film is still the best. I’ve watched it a dozen times, and will probably watch it a dozen more!
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