10 Best Movies About Dating

If you're looking for the ten best movies about dating, then you can't go wrong with these choices. When you're on a date, why not take her to see a movie about dating? It only makes sense to do so. There's plenty of romantic dating movies to choose from out there, some are funny, some packed with action, some are complete thrill rides, and some are even a little mixture of everything. Here's ten date movies you can't go wrong with.


  1. "The Night Before." Keanu Reeves plays a nerdy guy who gets a shot at taking the hottest girl in school on a date but it all transitions into a night of misadventure in downtown Los Angeles. A humorous and unconventional date movie set in a weird setting like this is bound to make for an interesting date.
  2. "License to Drive." Corey Haim plays a student who yearns to get his driver's license and take the hottest chick in school out for a spin, but he ends up failing the written part of the driver's test. That doesn't stop him from sneaking out of his house with his grandfather's car though. The ladies will be swept away by the dreamy Corey Haim, while the guys will drool over the sexy Heather Graham.
  3. "Mystery Date." When his older brother cleverly sets up a first date for him, Hawke finds himself getting mixed up with his brother and blamed for his crimes and troubles during the date. This is another great date flick if you're looking to spice things up with a little bit of comedy, mystery, and misadventure. 
  4. "Love Potion No. 9." Two biochemists manage to get their hands on a special love potion that causes people of the opposite sex to become infatuated with the person using it, simply by starting a conversation. Dating and sex have never been so fun as in movies as it is here, just the right amounts of each for your date.
  5. "Ten Things I Hate About You." A teenage boy tries to win the heart of the hottest girl in school with the help of his best friend, but there's one problem. She can't date until her older sister does.
  6. "Swingers." Vince Vaughn and an all-star cast make up this classic dating flick that zooms in on the lives of unemployed single actors who live in Hollywood. The guys have the male-dominated cast to look up to here, while the shy Jon Favreau is a great candidate for the ladies.
  7. "Free Enterprise." Think "Swingers" meets "Trekkies." This hilarious film portrays two "Star Trek" fanatics, one is an editor for a porn company and the other is a magazine editor who can't write a decent script. "Star Trek" and dating makes for a funny and entertaining package for both men and women.
  8. "Roger Dodger." Who doesn't want an uncle like Roger? He's a cynical and highly intelligent advertising copywriter who takes his 16-year-old nephew out on the town for the night in New York City in search of sex. This film is a clever exploration of the relationship between sex, men, and women, therefore it should provide some thought provoking discussion for you and your date.
  9. "Hitch." Need a date doctor? Call Hitch. This classic dating flick depicts Will Smith as a successful NYC dating doctor, who makes it his mission to help men meet the women of their dreams, until he meets his. "Hitch" has all the right date ingredients: humor, wit, charisma, and plenty of heart.
  10. "Jerry Maguire." Starring Tom Cruise in one of his biggest roles ever, this film gives a little something for both men and women. There's the sports aspect for the guys and the love story for the ladies.
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