Top 10 Boy-Friendly Valentine’s Day Movies

Top 10 Boy-Friendly Valentine’s Day Movies for the Perfect Movie Night


Valentine’s Day is a wonderful time to enjoy a heartwarming movie with a loved one. However, when it comes to planning a romantic movie night that will appeal to boys, it can be akin to pulling teeth. Thankfully, there are a lot of great options to satisfy romantics and action lovers alike. Whether it’s the excitement of swashbuckling adventures or the timeless appeal of classic tales, there are films that are sure to capture the imagination. From the late 80s to the early 2000s, there are a plethora of unique and unconventional romantic movies. Here are the top 10 boy-friendly Valentine’s Day movies for the perfect movie night.

Mr & Mss Smith (2005)
“A bored married couple is surprised to learn that they are both assassins hired by competing agencies to kill each other.” (IMDB)

The film follows the story of John and Jane Smith, a married couple who are both secret assassins assigned to kill each other. This movie makes a great Valentine’s Day movie for guys due to its unique blend of comedy and action. The premise provides an exciting and adrenaline-pumping experience that many men enjoy. Additionally, the movie offers a healthy balance of romance and comedy, making it a versatile choice that appeals to a wide audience. The ample eye candy provided by the two main characters doesn’t hurt either.

Brad PittJohn Smith

Angelina JolieJane Smith

The Princess Bride (1987)
“A sick boy’s grandfather reads him the story of a farmboy-turned-pirate who encounters numerous obstacles, enemies and allies in his quest to be reunited with his true love.” (IMDB)

“The Princess Bride” is known for its witty dialogue, fresh characters, and its ability to evoke a wide range of emotions. It’s a classic tale that parodies fairy tales, making it an entertaining choice for both men and women. The movie’s adventurous and swashbuckling elements, along with its timeless romance, make it a perfect pick for a Valentine’s Day movie night that guys can enjoy. “As you wish.”

Cary ElwesWestley

Robin WrightThe Princess Bride

Mike and Dave Need Wedding Dates (2016)
“Two hard-partying brothers place an online ad to find the perfect dates for their sister’s Hawaiian wedding. Hoping for a wild getaway, the boys instead find themselves out-hustled by an uncontrollable duo.” (IMDB)

“Mike and Dave Need Wedding Dates” tells the story of two hard-partying brothers who seek respectable dates for their sister’s wedding in Hawaii. The movie offers over-the-top humor and raunchy fun, making it an entertaining choice for a lighthearted Valentine’s Day movie night. While the film received mixed reviews, its focus on humor and the dynamics between the male characters make it a great option for a fun and relaxed Valentine’s Day viewing experience.

Zac EfronDave Stangle

Adam DevineMike Stangle

Anna KendrickAlice

Aubrey PlazaTatiana

Love Stinks (1999)
“Seth Winnick has it all: a successful career in television, good friends, and a passionate relationship with beautiful Chelsea. However, when he fails to make a timely marriage proposal, Chelsea tries to make his life hell.” (IMDB)

“Love Stinks,” an American black comedy, presents a dark and comedic take on relationships. The movie is centered around the challenges of a romantic relationship and is known for its cynical view of love and the dynamics between men and women. The movie has received varied reviews, with some viewers finding it hilarious while others find it a bit too harsh. The film’s focus on the darker aspects of relationships and its cynical perspective on love make it a unique choice for Valentine’s Day, particularly for those who prefer anti-romance movies. Therefore, “Love Stinks” may be considered a great Valentine’s Day movie for guys who appreciate its dark humor and unconventional take on love and relationships.

French StewartSeth Winnick

Bridgette Wilson-SamprasChelsea Turner

10 Things I Hate About You (1999)
“A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.” (IMDB)

The film “10 Things I Hate About You” is a great Valentine’s Day movie for guys due to its witty and sharp dialogue, relatable male characters, and a storyline that goes beyond traditional romantic clichés. The movie, inspired by William Shakespeare’s “The Taming of the Shrew,” features a strong male lead and addresses themes such as friendship, individuality, and the challenges of high school life, which can resonate with a male audience. Additionally, the film’s humor and well-developed male characters make it an enjoyable choice for Valentine’s Day viewing.

Heath LedgerPatrick Verona

Julia StilesKat Stratford

The Wedding Singer (1998)
“Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.” (IMDB)

“The Wedding Singer” (1998) is a delightful choice for couples and individuals alike. The film offers a nostalgic and lighthearted take on love and relationships, which can appeal to a male audience. Its 1980s setting, a spoof on the decade itself, provides a unique and entertaining experience. The movie’s enduring popularity and positive reception make it a suitable option for Valentine’s Day viewing, offering a balance of romance and humor that can be appreciated by both men and women.

Adam SandlerRobbie Hart

Drew BarrymoreJulia Sullivan

Scott Pilgrim Vs. The World (2010)
“In a magically realistic version of Toronto, a young man must defeat his new girlfriend’s seven evil exes one by one in order to win her heart.” (IMDB)

“Scott Pilgrim vs. The World” (2010) features comic-style fight sequences and killer musical numbers, making it a fun and entertaining choice for a movie night. Additionally, it offers a quirky departure from the typical love story, avoiding intense romantic themes while still being about love and relationships. This makes it a suitable option for couples who may not want anything too mushy. The movie’s focus on fantastical battles and its off-beat, indie feel can appeal to those looking for a different kind of Valentine’s Day film experience.

Michael CeraScott Pilgrim

Mary Elizabeth WinsteadRamona Flowers

Forgetting Sarah Marshal (2008)
“Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah’s traveling to the same resort as her ex – and she’s bringing along her new boyfriend.” (IMDB)

“Forgetting Sarah Marshall” can be a fun Valentine’s Day movie for guys due to its comedic take on breakups and moving on. The film offers a humorous and relatable portrayal of a man dealing with a difficult breakup, which can resonate with a male audience. The movie’s blend of comedy and romance, along with its all-star cast, makes it an enjoyable choice for Valentine’s Day viewing. The film’s focus on personal growth and finding new love after a heartbreak can be both entertaining and uplifting, making it a great option for those looking for a light-hearted, yet meaningful Valentine’s Day film experience.

Kristen BellSarah Marshall

Jason SegelPeter Bretter

Mila KunisRachel Jansen

Russell BrandAldous Snow

50 First Dates (2004)
“Henry Roth is a man afraid of commitment until he meets the beautiful Lucy. They hit it off and Henry think he’s finally found the girl of his dreams until discovering she has short-term memory loss and forgets him the next day.” (IMDB)

“50 First Dates” presents a heartwarming take on love. The film tells the story of a man who falls in love with a woman with short-term memory loss, causing her to forget him each day. This premise, combined with the film’s humor and genuine emotional moments, makes it a compelling choice for Valentine’s Day viewing. Its focus on the male lead’s unwavering commitment and efforts to win over his love interest every day can resonate with a male audience, offering a blend of romance and comedy that is both entertaining and touching.

Adam SandlerHenry Roth

Drew BarrymoreLucy Whitmore

The 40 Year Old Virgin (2005)
“Goaded by his buddies, a nerdy guy who’s never “done the deed” only finds the pressure mounting when he meets a single mother.” (IMDB)

“The 40-Year-Old Virgin” (2005) offers a humorous and relatable portrayal of a man navigating the complexities of relationships and intimacy. It’s surprisingly insightful and has a good heart, making it an enjoyable choice for Valentine’s Day viewing. The movie’s focus on the lead character’s personal growth and his interactions with friends and love interests can resonate with a male audience, offering a balance of humor and heartfelt moments.

Steve CarellAndy

Catherine KeenerTrish

Hopefully this list provides you with a diverse selection of boy-friendly Valentine’s Day movies that will delight your movie night. From action-packed adventures to charming romantic comedies, these films cater to a broad range of tastes. Whether you’re planning a cozy family evening or a laid-back celebration with friends, these movies offer the perfect blend of humor, romance, and relatable stories. So, grab some popcorn, settle in with your loved ones, and enjoy the magic of these top 10 movies that are sure to make your Valentine’s Day special. Happy watching!