The charm and chaos of the disastrous first date was an integral part of thenow endangered genre of romantic comedy. It is hard to identify what makes a date in modern times in film, as intimacy between two complete strangers can be difficult to explore in an honest and engaging way.
Thevague lines between sex, intimacy, attraction, and hatredare explored in the first dates of these films. Different circumstances bring these characters to their first date and the eventual chaos. Some never make it, but most do. After all, bad dates unfortunately make great icebreakers. Here are 10 films about disastrous first dates, which either make a relationship or remain a big mistake forever.
10When Harry Met Sally.
When Harry and Sally meet inWhen Harry Met Sally…for a cross-country drive,Sally immediately despises him for his views on women and love. Harry, played by Billy Crystal, is a cynic and sardonic in his tone about love and life in general. On the other hand, Sally is naive and believesmen and women can be just friendswithout sex being an interference. Harry disagrees. It can be debated if their first meeting was their first date since Harry was in a relationship with Sally’s friend, but Harry was openly flirting with Sally, and it was clear that he was drawn to her. Although, the same cannot be said about Sally, who was repelled by him, almost the instant he opened his mouth. They part ways and meet again after 5 years later, and Sally rejects the offer of being his friend, again!
Related:How When Harry Met Sally… Changed Romantic Comedies
9The 40-Year-Old Virgin
The 40-Year-Old Virginwill definitely make it to the hall of fame of disastrous first movie dates. Directed by Judd Apatow, the film is centered around Andy Stitzer who is embarrassedabout being a virgin at 40. Andy works in a big-box store and one unfortunate night, his colleague finds out about his secret and make fun of him. Andy is devastated and is helped by his friends to get over his anxiety with women. Thus begins a string of bad speed dates where he applies the bad advice his colleagues teach him, which only makes him seem foolish.
The funniest of all is when he is approached by a woman who has mostly had sex with other women and wants to transition to having sex with men. She finds Andy to be appropriately feminine, perfect for her transition.
Also, who can forget the hilarious scene when Andy has to distract himself from his date’s nip slip? Later, when Andy finds his match in Trish, his bad luck still looms over his head as Trish’s daughter catches them almost having sex.
8Back to the Future
In hindsight, someone needs to investigate what was happening in the writer’s room which scriptedBack to the Future.The era defining science fiction directed by Robert Zemekis stars Michael J. Fox as Marty McFly, who accidentally time travels to 1955 through the DeLorean automobile, designed by the scientist Dr. Emmett Doc Brown. However, he finds out that in 1955 he was a potential lover to his own mother, Lorraine, and needs to somehow get his parents together so that he can be born in the future.
Things get really awkward when Lorraine opens up about her feelings for Marty and later asks him to the school dance. Marty plots to make inappropriate advances on Lorraine so that her one-sided lover Steve, Marty’s future father, comes to the rescue. Hell breaks loose as the bully Biff comes in between the three. However, Steve stands up for Lorraine and they thankfully kiss, confirming Marty’s future birth.The ’80s were wild!
7What Happened Was
The indie classic,What Happened Was,was the winner of the Sundance Film Festival, which surprised everyone. The film was directed by Tom Noonan andshows the insecurities of a first dateand how one hides their genuine side on dates. In the film, two loners meet on their first date. Jackie, played by Karen Sillias, is an executive assistant who finds Michael, played by Noonan, intriguing. The latter is a paralegal, and both usetheir own tactics to get to know each other. The night reveals an unsettling discussion between the two when they discover unpleasant surprises. The film shows the difficulties in connecting with strangers in the modern world and how dating is not as glamorous and sensuous as seen in films.
6How to Lose a Guy in 10 Days
This film is designed around the idea of the horrible first date, and the title should not surprise anyone.How to Lose a Guy in 10 Daysstars Kate Hudson as Andie Anderson, who is an advice columnist who ironically works on a piece that details a plan to get rid of guys in 10 days. However, she needs a guinea pig to test her scheme. Andie meets Ben, played by Matthew McConaughey, who claims to make women fall in love with him in 10 days.
Since this is a movie, of course they had to meet! The two, who are diametrically opposed, meet and Andie tries her best to drive away Ben. Initially, both hide their true intentions when they meet, but slowly Ben begins to get irritated by Andie’s tactics and almost breaks up with her. However, to remind everyone this is a romantic comedy, they end up just fine.
5Along Came Polly
The romantic comedyAlong Came Pollycan make one slightly nostalgic about the Ben Stiller era when the actor reigned in tangy romantic comedies. In the film, Stiller plays Reuben, a risk-averse actuary for a life insurance policy who catches his newly-wed wife cheating on him with a French scuba instructor in their honeymoon. Devastated, he tries to start fresh and runs into his junior high school classmate Polly Prince in an art gallery and is immediately smitten by her. Unfortunately, the first date is horrendous as Reuben is pushed to be more adventurous by his new date. They eat in a Moroccan restaurant, which gives him irritable bowel syndrome, disrupting the entire date. However,Polly is spontaneous and gives him another chance.
4What Happens in Vegas
It is one thing to have a bad date, but it is a whole other ballgame when you end up marrying a complete stranger you meet in Vegas. That is pretty much the plot ofWhat Happens in Vegas.The film stars Cameron Diaz as Joy McNally,who is dumped by her fiancé. On the other hand, Jack Fuller,played by Ashton Kutcher, is firedby his dad-cum-boss. Both find themselves in Las Vegas on a literal unforgettable night when they get drunk and get married. When they wake up after their wild night, they decide to file for a divorce. However, Jack uses a quarter given to him by Joy in a slot machine and ends up hitting a three million dollar jackpot. To complicate the matter further, the divorce court judge declares he cannot grant divorce until the couple attempts to co-exist for six months.
3Knocked Up
Speaking of bad dates, inKnocked Up,a drunken one-night stand turns into an unwanted pregnancy. The film stars Katherine Heigl as Alison Scott, who meets Ben, a Canadian slacker,played by Seth Rogen, who is living off injury compensation funds, in a nightclub. After a drunken night and unprotected sex, they both part knowing they have nothing in common.
Eight months later, Alison realizes she is pregnant and wants to keep the baby. However, she approaches Ben to give him a chance of being a worthy father to her child. Ben gets his coming-of-age moment with this experience as he realizes he has to finally grow up. The relationship between the two almost feels like a prolonged bad date where both are never on the same page about anything. Thankfully, things fall in place as Alison approaches her delivery and Ben finally learns to prioritize his responsibilities.
2Pulp Fiction
Many would agree that the rendezvous between Vincent Vega and Mia inPulp Fictionis a version of a first date gone wrong, in classic Tarantino-style. The film has a non-linear structure that follows a day in the life of hitman Vincent Vega, played by John Travolta and Jules Winnfield,played by Samuel Jackson. The film shows several characters who get in the way of the two and one of them is Mia Wallace, played by Uma Thurman, who is gangster Marsellus Wallace’s trophy wife. Vincent is assigned to take Mia around and they both enjoy a wonderful date as they eat and dance at a 1950s themed restaurant. However, hell breaks loose when Mia overdoses on heroin and almost dies. Vega and his druggie friends come to the rescue, and she is dropped at her home safe and sound, almost.
Related:10 Best Romantic Comedies Directed by Women You Shouldn’t Skip
1Blind Date
You know a date is about to go south when it comes with a disclaimer. This happens with Walter Davis,played by Bruce Willis, who is set up with Nadia Gates, played by Kim Basinger, Davis’s sister-in-law’s cousin inBlind Date. Walter is warned by his brother to not let Nadia drink alcohol, which he takes lightly but regrets later. The night begins awkwardly but gets worse when Davis is assaulted several times by Nadia’s ex-boyfriend, and he reveals her wild side after getting drunk. The film was a critical failure but a box-office successwith several laugh-out-loud moments.
