20 Best Movies To Watch With Your Boyfriend

20 Best Movies to Watch With Your Boyfriend
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One thing we learned during COVID-19 lockdowns is that one of the best ways to bond with your partner is through watching movies right from the comfort of your home. A good movie and ample creativity would surely make everything worthwhile. You can prepare a bowl of popcorn, and everything is settled. However, finding a suitable film is quite challenging, especially when both of you have very different tastes in movies. Here are some suggestions for the best movies to watch with your boyfriend. Enjoy!

#20 My Best Friend's Wedding (1997)

Director: P. J. Hogan

Box Office: $299.3 million

Starring: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett, Philip Bosco

Synopsis:

Childhood friends Michael O’Neal and Julianne Potter made a pact to get married if they were still single at age 28. Now, O’Neil says he’s marrying Kimberly, a stunning 20-year-old, four days before her 28th birthday. As soon as Julianne acknowledges that she is genuinely in love with him, she makes an unwavering commitment to thwart the wedding. However, things become much more complicated when she is chosen as the maid of honor.

#19 The Proposal (2009)

Director: Anne Fletcher

Box Office: $317.4 million

Starring: Sandra Bullock, Ryan Reynolds, Malin Åkerman, Craig T. Nelson, Mary Steenburgen, Betty White

Synopsis:

A successful self-made chief editor at Ruick & Hunt Publishing in New York, Margaret Tate is despised by her employees. Margaret, who lost her parents when she was sixteen, is unforgiving toward the office staff. Andrew Paxton, her executive assistant, and aspiring editor. He has worked with her for three years without receiving any attention. Margaret blackmails Andrew into getting married when she runs into issues with immigration because her visa has expired and she faces deportation. He would receive a promotion to the editor in exchange, and she would release his book.

During this time, Margaret and Andrew would have an interview with the immigration department’s skeptical Mr. Gilbertson after the weekend. Andrew’s friendly family greets Margaret as the pair visits Sitka, Alaska, to honor Andrew’s grandmother’s 90th birthday. She gets to know Andrew’s family more throughout the weekend, and they propose to her in their barn, following a Paxton family custom. As Mr. Gilbertson suddenly shows in Sitka with the threat of accusing Andrew of fraud, the anxiety only grows.

#18 Bridget Jones's Diary (2001)

Director: Sharon Maguire

Box Office:  $282 million

Starring: Renée Zellweger, Colin Firth, Hugh Grant, Jim Broadbent, Gemma Jones

Synopsis:

Bridget Jones is a typical woman who battles her age, weight, career, absence of a man, and numerous flaws. Bridget resolves to take charge of her life as part of her New Year’s resolution, and she begins by maintaining a diary in which she will always be completely honest. The fireworks start when her endearing but dishonest boss shows interest in the eccentric Miss Jones. Bridget’s group of slightly odd friends and a disgruntled acquaintance, who Bridget can’t help but run into and find quietly attractive, are added to the mix.

#17 It's Complicated (2009)

Director: Nancy Meyers

Box Office:  $224.6 million

Starring: Meryl Streep, Steve Martin, Alec Baldwin, John Krasinski

Synopsis:

Jane has been a successful bakery shop owner and divorcee for ten years. The two were brought together at a family event and realized they were still attracted to each other. The feelings disrupt their current lives, and soon enough, they find themselves rekindling the love they shared ten years ago. However, things were already complicated at this time. Jake, a lawyer, is already remarried to a much younger woman and has a son. Jane becomes the other woman in the relationship, making things very complicated.   

#16 To All the Boys I've Loved Before (2018)

Director: Donald Petrie

Box Office:  $177.5 million

Starring: Kate Hudson, Matthew McConaughey, Adam Goldberg, Michael Michele, Shalom Harlow

Synopsis:

Lara Jean Covey, a teenager, lives a typical, monotonous high school existence until some surprising letters are sent to all of her old crushes. These were private love letters only intended for her to read, but one day her sister Kitty decided to share them to make Lara Jean’s life more fascinating. At school, when these lads begin to approach her about their letters, her life is thrown into chaos. These boys include Peter Kavinsky, her arch-enemy Gen’s lover, and Josh, who also happens to be her neighbor and the boyfriend of her older sister Margot. Lara Jean discovers herself and perhaps even a meaningful connection through a series of highly bizarre incidents.

#15 How to Lose a Guy in 10 Days (2003)

Director: Donald Petrie

Box Office:  $177.5 million

Starring: Kate Hudson, Matthew McConaughey, Adam Goldberg, Michael Michele, Shalom Harlow

Synopsis:

Ad executive Benjamin is vying for a huge contract, but his employer feels like it requires a feminine touch, so he’s thinking of giving it to a couple of female executives. With their help, Benjamin bets that he will win the account if he can get a woman to fall in love with him. He lets the female executives pick the woman. They decide on Andie, a Composure magazine writer they had previously met and discovered was working on an article titled “How to Lose a Guy in 10 Days.” They don’t let him know that they are aware she will be impossible. While she does her best to push Ben away, Ben makes an effort to win her over.

#14 Definitely, Maybe (2008)

Director: Adam Brooks

Box Office: $56 million

Starring: Ryan Reynolds, Isla Fisher, Derek Luke, Abigail Breslin, Elizabeth Banks, Rachel Weisz

Synopsis:

When Will Hayes, a 30-something Manhattan father, is going through a divorce, his 10-year-old daughter Maya begins to probe about his life before marriage. Maya is incredibly curious about how her parents met and fell in love. Will’s story starts in 1992 when he is a young, idealistic aspirant politician who relocates from Wisconsin to New York to serve on the Clinton campaign. Will relived his past for Maya when he was an idealistic young man discovering the ins and outs of big city politics. He recalls the details of his relationships with three very different women. Will’s closest friend during the campaign is Russell McCormack. They share the same type of girl problems. Will tries his best to keep the story appropriate for her daughter’s young ears while she attempts to guess who he finally married.

#13 Always Be My Maybe (2019)

Director: Nahnatchka Khan

Box Office: N/A

Starring: Ali Wong, Randall Park, James Saito, Michelle Buteau, Vivian Bang, Daniel Dae Kim, Keanu Reeves

Synopsis:

Sasha and Marcus were great friends growing up as neighbors in San Francisco. Because her parents aren’t usually home for dinner, Sasha frequently eats at Marcus’ place. Sasha learns a lot about cooking from Marcus’s mother. While Marcus’s mother passed away when they were a teenager, the two grew even closer. Meanwhile, Marcus tells Sasha he won’t be attending college. When she presses him about it, he snaps at her and claims it was his mother who passed away rather than hers. Sasha departs, upset and furious, and they cease communicating. Years later, they would meet again. Can the love be rekindled once more?

#12 Along Came Polly (2004)

Director: John Hamburg

Box Office: $178.3 million

Starring: Ben Stiller, Jennifer Aniston, Debra Messing, Philip Seymour Hoffman, Alec Baldwin

Synopsis:

The person Reuben Feffer believes to be his true love cheats on him with a scuba instructor while they are on their honeymoon. To reclaim his life, Reuben returns home. Reuben runs across Polly Prince, an old buddy from high school, while out with his best friend, Sandy Lyle. The moment they meet, Reuben senses a connection and immediately starts wooing her. However, Reuben will find it difficult because he spends his days analyzing risks, and something unexpected happens. 

#11 The Notebook (2004)

Director: Nick Cassavetes

Box Office: $117.8 million

Starring: Ryan Gosling, Rachel McAdams, James Garner, Gena Rowlands, James Marsden, Kevin Connolly, Sam Shepard, Joan Allen

Synopsis:

A senior citizen with dementia and memory loss is read a love story by nursing home resident Duke. It is about a  wealthy 17-year-old, Allie Hamilton. She is on summer vacation in Seabrook in the late 1930s. Local laborer Noah Calhoun meets Allie at a fair and quickly falls in love. One day, Noah takes Allie to a country house he imagines purchasing and restoring. They make love but are disturbed by their friend. 

Since Noah belongs to a different social class, Allie’s parents disapprove of the relationship. They drag her to New York because they disapprove of their relationship.  Each day of the year, Noah writes Allie letters, but her mother, Anne Hamilton, never gives them to her.  

In the following three years, the United States enlisted in World War II, Noah and his best buddy Fin enlisted in the military, and Allie served as an army nurse. In the hospital, she runs into wounded soldier Lon Hammond. After the war, they reconnect and go on dates. Lon, who is affluent and attractive, then pops the question. Meanwhile, numerous people are interested in purchasing the old house that Noah bought and restored. Allie returns to Seabrook and sees Noah. She becomes torn between her first love and her commitment to Lon when she unintentionally sees the picture of Noah and his home in a newspaper. In the ending scene, Duke stops reading to the old lady since his children came to visit. 

#10 The Princess Bride (1987)

Director: Rob Reiner

Box Office: $30.9 million

Starring: Cary Elwes, Mandy Patinkin, Chris Sarandon, Christopher Guest, Wallace Shawn, André the Giant, Fred Savage, Robin Wright

Synopsis:

A young boy’s granddad stops to see him when he becomes ill. To cheer up his grandson, Grandpa sent a book about the love between the lovely Buttercup and the enamored Westley, a love that was sadly cut short by Westley’s terrible apparent death at sea while seeking his riches. Buttercup, who has vowed never to fall in love again after experiencing heartbreak, agrees to marry the wealthy and attractive Prince Humperdinck, the heir to Florin’s kingdom. Death, however, is no barrier to true love, and in a tale featuring exotically embellished sworders, big-hearted giants, clever kidnappers, sadistic tormentors, vile swamps, rodents of Unusual Size, the Dread Pirate Roberts, and a somewhat tired miracle worker, Westley and Buttercup’s love takes many unexpected turns along an exciting path.

#9 Sleepless in Seattle (1993)

Director: Nora Ephron

Box Office: $227.8 million

Starring: Tom Hanks, Meg Ryan, Bill Pullman, Ross Malinger, Rob Reiner

Synopsis:

After Sam Baldwin’s wife passes away, he and his son Jonah decide to relocate to Seattle. When Jonah realizes how depressed his father is, he phones a radio doctor, who gives him the nickname Sleepless in Seattle since Jonah claims he has trouble falling asleep. When he begins to talk about his wife, women from all over the nation start to listen. One woman, Annie, who lives in Baltimore, can’t help but be charmed by his story. Even though she is engaged, Annie can’t help but think of Sam. She quickly looks into him and even travels to Seattle to meet him. Sam, who is at the airport to see someone off, notices her as soon as she steps off the plane and cannot take his eyes off her. He tries to follow her but is unable to do so. Jonah, who has been sifting through his father’s mail since he was on the radio, discovers the letter Annie wrote on a whim but didn’t send—her friend did. He tells his father that this might be it. Sam, though, doesn’t believe he could be in a relationship with someone who lives so far away.

#8 Harry Potter Series (2001-2011)

Director: Chris Columbus (1-2), Alfonso Cuaron (3), Mike Newell (4), David 

Box Office:  $7.7 Billion (Total)

Starring: Daniel Radcliffe, Rupert Grint, Emma Watson

Synopsis:

The “Harry Potter” series is one of the childhood favorites of a lot of people. It talks about the tale of a young British Wizard named Harry, the boy who lived and his journey as he navigates through the unfamiliar wizarding world. Having been raised by her muggle aunt Petunia and her husband, Vernon, Harry was fully aware of the existence of witches and wizards. The trajectory of his life changed when he turned 11. He received an acceptance letter from Hogwarts School of Witchcraft and Wizardry, and everything started from there. The film series is composed of eight movies which mean eight different adventures.

#7 The Kissing Booth Series (2018-2021)

Director: Vince Marcello

Box Office:  N/A

Starring: Jacob Elordi, Joey King, Joel Courtney

Synopsis:

Elle Evan grew up close to her mom’s best friend’s family. As a matter of fact, she also became best friends with her mom’s best friend’s son, Lee. The two are very close to each other to the point that they’re practically siblings. The pair have a series of rules that they must abide by to maintain their friendship. However, Elle slowly broke one of the most significant rules: never to date your best friend’s sibling. Elle fell in love and started dating Noah, Lee’s older brother. Noah was a jock who always got into trouble. He was also famous among the girls. Elle uses Noah’s popularity for their club’s booth, a kissing booth. 

#6 When Harry Met Sally (1989)

Director: Rob Reiner

Box Office:  $92.8 million

Starring: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby

Synopsis:

After finishing college in Chicago, Harry and Sally get to know one another while traveling to New York for 18 hours by vehicle. Harry’s opinion that a man and a woman can never be merely friends because he will always want to have sex with her makes them click less than they might have hoped. They occasionally cross paths throughout the following ten years and quickly become close friends. They divulge personal information about their ambitions, dreams, disappointments, and accomplishments while also falling in love. However, it is unclear whether they would be able to maintain their relationship after having sex.

#5 50 First Dates (2004)

Director:  Peter Segal

Box Office:  $198.5 million

Starring: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Dan Aykroyd

Synopsis:

Henry Roth enjoys the companionship of countless free-spirited ladies while living in the Hawaiian paradise. Up until he meets Lucy Whitmore, that is. Both Henry and Lucy enjoy one another’s company and sense the beginning of a committed relationship. The following day, when Henry approaches Lucy, he is perplexed when she doesn’t acknowledge him. Henry learns that Lucy has short-term memory loss and cannot recall daily. Henry is ready to make her fall in love with him repeatedly every day and will not let this deter him from doing so.

#4 Notting Hill (1999)

Director: Roger Michell

Box Office:  $363.9 million

Starring: Julia Roberts, Hugh Grant, Hugh Bonneville, Emma Chambers, James Dreyfus, Rhys Ifans, Tim McInnerny, Gina McKee

Synopsis:

William Thacker, a bookseller in a store in West London’s Notting Hill neighborhood, lives with his eccentric Welsh buddy Spike. One day, while William minds the shop, Anna Scott, a stunning and well-known American actress in London filming a movie, strolls in. She approaches William to purchase a book, and he responds politely and charmingly, just as a famous actress might to a star-struck salesperson. If William hadn’t left a little while later to purchase some juice, their relationship would have logically come to an end. He stumbles with Anna on the street as he runs back to the store, spilling juice all over her top. William offers to let her clean up at his place since he lives close; Anna accepts because William seems like a nice enough guy. They kiss just as Spike arrives because Anna needs to return and get a bag she left at William’s place. His friends, family, and the general public openly ask what he is doing dating a movie star as a relationship develops.

#3 Pretty Woman (1990)

Director: Garry Marshall

Box Office:  $463.4 million

Starring: Richard Gere, Julia Roberts, Ralph Bellamy, Jason Alexander, Héctor Elizondo, Laura San Giacomo, Alex Hyde-White

Synopsis:

Vivian Ward, a young prostitute, imagines a guy in the shape of a knight saving her. In an unexpected turn of events, she ran upon the dashing billionaire Edward Lewis, who was driving his friend’s sports car and had been disoriented on the street. Instead of accepting her request for a date, he asked her to show him how to get back to his hotel. Vivian operated his vehicle. When they entered the motel, Vivian received $20 from Edward in exchange for her assistance. When he turned around as he was ready to walk into the hotel and noticed her sitting on the corner, he found it difficult to let her go because she was beautiful. She is invited to accompany him into his penthouse suite.

After making love and getting to know one another that night, Vivian was shocked the next morning when Edward asked her to stay with him for seven days in exchange for payment. It was accepted with joy by Vivian. Vivian’s world changes due to spending the entire week with Edward, far from her life as a Hollywood Boulevard prostitute. She was also progressively falling in love with him on top of all that. Edward, however, views things from a different angle.

#2 You've Got Mail (1998)

Director: Nora Ephron

Box Office:  $250.8 million

Starring: Tom Hanks, Meg Ryan, Parker Posey, Jean Stapleton, Dave Chappelle, Steve Zahn, Dabney Coleman, Greg Kinnear

Synopsis:

The film focuses on the love story of some of New York’s competing book retailers. Kathleen Kelly is a proud owner of a small but famous children’s bookstore called The Shop Around the Corner. She is in a relationship with a pretty renowned journalist, Frank Navasky. Despite the happy relationship, she still sought someone she could correspond with and found someone online. They only knew each other by their internet handles “Shopgirl” and “NY152.” The anonymous correspondence between the two continues. However, the two of them would unknowingly know each other when Joe Fox, a man coming from the infamous competitor bookstore chain Fox & Sons. Joe’s arrogance annoyed Kathleen greatly, and she would continuously chat with her online friend. Everything spirals out of control when Joe finds out that his online chatmate is Kathleen Kelly.

# 1 Friends with Benefits (2011)

Director: Will Gluck

Box Office:  $149.5 million

Starring: Justin Timberlake, Mila Kunis, Patricia Clarkson, Jenna Elfman, Bryan Greenberg, Richard Jenkins, Woody Harrelson

Synopsis:

Both Dylan Harper and Jamie Reillis are unlucky when it comes to love. Dylan Harper, a Los Angeles-based art director, is persuaded by executive recruiter Jamie Reillis to accept a position at the GQ magazine office in New York. They discover they have a lot in common and quickly become friends. Dylan and Jamie decide to stop hunting for real love and put more emphasis on having fun after becoming jaded by several failed relationships. However, issues arise when the two closest friends incorporate sex into their relationship.

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