Romantic Comedy Movies

Romantic comedy movies know no age or time. They were there when you were a kid, and they are still here now. If you are like many older adults, you may find the ‘new generation’ of romantic movies to be unsatisfactory, and many will agree. The gentlemanly actions that made every girls heart melt in your time are replaced with arrogant, narcissistic characters. Is it possible to even find a romantic comedy that will make you laugh and cry at the same time?

We’ve put together a list of what we believe are some of the best Romantic comedy Movies that are not so new and not so old either. We can’t promise they will meet the standards of My Fair Lady, but they are definitely worth a watch.

While You Were Sleeping

Starring hilarious Sandra Bullock and Bill Pullman, the comedy stars Lucy who works as a fare token collector and has a crush on a regular commuter named Peter. In an unexpected turn of events, she rescues her crush from an oncoming train. At the hospital, nurses misunderstand Lucy to be his fiancé and Lucy ends up playing along until she meets Peter’s older brother Jack who she falls in love with.

While you were sleeping is a great blend of innocent comedy with playful romance and honesty that will make you shed tears of laughter and joy at the same time.

Letters to Juliet

The film is inspired by the non-fiction book bearing the same title and stars Amanda Seyfried, Vanessa Redgrave, and Christopher Egan. It is an inspirational story, especially for seniors, as it follows the quest of Claire (Redgrave) to find her first love, Lorenzo. The trio begins their journey by locating all the “Lorenzo’s” in the area and visiting them one by one. They are met with amusing reactions from different Lorenzo’s who fall at elderly Clair’s feet. Along the way, Sophie (Amanda) and Clair’s grandson Charlie (Christopher) fall in love.

The movie features beautiful scenery and leaves a lasting impression on viewers implying that it is never too late to find love.

Notting Hill

This movie follows the unlikely love story of a movie star (Julia Roberts) and a bookshop owner (Hugh Grant). After an accidental meeting at the bookshop, Grant spills a drink on the movie star and convinces her to change at his apartment. In a whirlpool of events including a tabloid scandal, the two lovers find themselves caught between their love and Robert’s career.

Notting Hill is not as boisterous as other comedy movies but offers a unique take on relationships between two with different lifestyles and how such romances at times work out.

You’ve Got Mail

This 90’s flick has the catchy line “Someone you pass on the street may already be the love of your life.” Starring Meg Ryan and Tom Hanks. The story is about the owner of a large bookstore (Tom) who starts putting the owner of a local bookstore (Meg) out of business. The couple are unknowingly corresponding over the internet and feel they have an attraction but can’t stand each other in person.

You’ve got mail has a positive message about how you may already know the person you are meant to be with but don’t’ know it.

The Proposal

The Proposal stars Sandra Bullock (Margaret) and Ryan Reynolds (Andrew) who have a boss-employee relationship at a Publishing company. When hard-driving Margaret faces deportation, she schemes to marry Andrew and promises him a promotion in return. There are a lot of side-splitting scenes like when Margaret gets down on her knees in the middle of a busy side street to “propose” to Andrew. The movie takes a turn, and the two end up falling in love with each other but not before many comical events unfold.

The movie is both funny and ‘educational’- teaching viewers that love requires sacrifice.

27 Dresses

A romantic comedy that will appeal to the younger generation but still has a few laughs for the seniors out there. Jane (Katherine Heigl) has been a bridesmaid 27 times and never a bride. Jane is faced with a dilemma when her secret crush (her boss) falls in love with her visiting baby sister. In a whirlwind romance, her crush and sister get engaged and ask Jane to plan their wedding. Meanwhile, a cynical writer, Kevin falls for her, which causes an unexpected turn of events leading to Jane finally becoming a bride.

The moral of the movie can be summed up like this: don’t change who you are to get love. Be yourself, and the right one will come along.

Mamma Mia

If you are a fan of ABBA, this is a must-watch. The film stars Sophie (Amanda Seyfried) and her mom Donna (Meryl Streep).  Sophie is a bride-to-be who invites three men to her wedding without her mother’s knowledge. These three men are her ‘potential fathers’ and Sophie believes she will know who her father is if she spends time with him. The movie features ABBA songs making you want to dance around in your living room.

Runaway Bride

This 90’s film stars the duo Richard Gere and Julia Roberts. The storyline revolves around Maggie (Roberts) who has run away from her wedding multiple times and Graham (Gere) a New York Columnist who writes about her. His article contains factual errors which cause him to lose his job. In an attempt to clear his reputation, he decides to travel and meet Maggie, who is about to get married again. Gere wants to prove that Maggie will run like she always does but ends up falling for her. The unsuspecting couple fall in love and Gere finds himself on the receiving end of Maggie’s running.

The movie offers the lesson of being yourself, knowing who you are, and not seeking to be a people pleaser in relationships

My Best Friend’s Wedding

Starring Julia Roberts as Julianne, this movie is the story of two best friends who vow to marry each other if they were single by the time they were 28.  Just three weeks before her 28th birthday, Michael breaks the news that he will marry Kimmy (Cameron Diaz) in four days. Julianne turns to sabotage the relationship by enlisting the help of her gay friend. This sabotage continues until the day of the wedding and succeeds to a degree.

The movie has a bittersweet theme leaving viewers shocked that things didn’t turn out as they imagined.

How to Lose a Guy in 10 Days

Released in 2003, How to Lose a Guy in 10 days stars Andie (Kate Hudson) and Ben (Matthew McConaughey) who make opposite bets. Andie bets she can lose a guy in 10 days while Ben bets that he can get a girl in 10 days. The two have evident chemistry that can be felt throughout the movie that has a dramatic end with Ben chasing after Andie’s taxi and revealing his true feelings.

The Wedding Singer

Duo Adam Sandler and Drew Barrymore have shown their chemistry in the past, and they show it again in this movie. In the film, both are engaged to the ‘wrong’ people, and as they are preparing for their weddings, their wrong decision becomes clear. The movies have a mid-80’s approach with excellent music choices giving an all in one package deal.

50 First Dates

There is no one I know who hasn’t watched this movie but in case you haven’t, it is considered classic in the romantic comedy genre.  It follows the story of Henry (Adam Sandler) a known womanizer who falls for Lucy (Drew Barrymore) a teacher who has no short-term memory. Because of Lucy’s condition, Hendry has to win her over daily and remind her of their relationship. In time, Henry makes a video that explains to Lucy that they are lovers which she plays every morning.

Women in particular love the movie because it shows how far a man will go for the one he loves while men may wonder if they’ll ever meet someone deserving of such effort.

Sleepless in Seattle

This film features the hardships and benefits of those in long distance relationships. The movie is about recent widower Tom hanks and newspaper writer Meg Ryan who live on opposite sides of the country. The son of widower Tom Hanks calls a radio station in an attempt to get his father a wife. Many women respond including Annie, a newspaper writer. Annie is infatuated with the story despite being engaged and decides to write to Sam


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