10. Grease (1978)
In this classic unrealistic love story, Danny Zuko (John Travolta), the bad boy of his high school, falls in love with his goody-goody summer fling Sandy Olsson (Olivia Newton-John). Things seem to be looking up for these two when they realize that Sandy has transferred to Danny’s school, but their personalities are polar opposites, and their friends are definitely not helping them get together.
9. Moulin Rouge (2001)
Satine (Nicole Kidman) easily lures in Christian (Ewan McGregor), an inexperienced and naive poet, with her courtesan charm. This relationship is doomed from the start because Christian does not have enough money to satiate his material girl, and Satine is professionally forbidden from love...well at least from choosing her own lover. But fortunately, anything can happen in the movies.
8. I Love You Beth Cooper (2009)
We all have those crushes that we know will never work out, the ones that will always remain fantasies. After super nerd Denis Cooverman (Paul Rust) professes his love for the most popular girl in school, Beth Cooper (Hayden Panettierre), at his high school graduation, his dream actually becomes reality…well at least for a night.
7. You’ve Got Mail (1998)
In this digital society people often rely on technology to communicate with a significant other. But really? An email relationship? Even overlooking this strange form of communication, Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan) were destined for failure. He is a big, mean, business owner, and she is trying to keep her small mom-and-pop bookstore out of his grasp.
6. Titanic (1997)
Rose DeWitt Bukater, a member of the upper class who is engaged to a wealthy, conniving man, falls for the humble and spontaneous Jack Dawson (Leonardo DiCaprio). Their relationship is exciting and fun, but it would never work out in real life, especially if Rose won’t even share her plank of wood with Jack when the unsinkable Titanic goes down in the middle of the Atlantic.
5. The Graduate (1967)
Benjamin Braddock (Dustin Hoffman) thinks he can handle a cougar when he falls for his father’s friend’s wife, Mrs. Robinson. But this affair ruins his chances at real love before it even starts when he realizes that his heart belongs to Mrs. Robinson’s daughter, Elaine (Katharine Ross). Why would she ever go for her mom’s sloppy seconds…bleh!
4. 50 First Dates (2004)
Henry Roth (Adam Sandler) thinks he has met the most beautiful, perfect girl in the world when he stumbles upon Lucy Whitmore (Drew Barrymore). The only problem is she has short-term memory loss and forgets him every time she goes to bed. It must get really annoying re-introducing yourself to a significant other every day. If it were me, I would have been out of there by date two.
3. Summer Catch (2001)
Ryan Dunne (Freddie Prinze Jr.) and Tenley Parrish (Jessica Biel) play out the classic dynamic of the rich girl falling in love with the poor boy. The parents obviously disapprove, which shouldn’t be a big deal since they are from different worlds and want different futures, right? But dang it, they are in love. At the very least, it was a good summer fling – he mowed her lawn, and she pranced around in a bathing suit.
2. Forgetting Sarah Marshall (2008)
Peter Bretter (Jason Segel) gets it on with Rachel Jansen (Mila Kunis), an employee at the hotel he is staying at in Hawaii. Basically, he’s a lucky bastard. In real life, the only people you “meet” at hotels are prostitutes and annoying tourists. Had the movie gone the prostitutes route, it would’ve been called Forgetting Crabs. Zing.
1. Never Been Kissed (1999)
Josie Geller (Drew Barrymore) crushes on a high school teacher, Sam Coulson (Michael Vartan), when she re-enrolls in her alma mater to perform research for a story. Not only does he think she is jail-bait, but there’s no way this relationship will work when he finally finds out who she really is… a 25 year old copy editor for the Chicago Sun-Times who has never been kissed. I mean, right?
Source: http://www.dailyfill.com/10-Most-Unrealistic-Romances-in-Summer-Movies-29436/