Romantic films are more prone to making spectacles out of bad dates than they are at orchestrating good ones, because it makes for a good laugh and a good story. Here are some of the most disappointing, embarrassing, and awkward dates in romantic film history that should make you feel pretty good about the time that guy asked to keep your pantyhose...
#15 // WORST DATE SETTING: He's Just Not That Into You
Mary (Drew Barrymore) recaps her date with a guy she connected with on MySpace and reveals that their coffee date was actually via video chat. Super romantic.
#14 // WORST PREMATURE BLOW-OFF: He's Just Not That Into You
Gigi (Ginnifer Goodwin)
is on a date in a guy's apartment and he gives her some crap about
being out of town soon, so he won't be able to call her. She excuses
herself to go to the bathroom to call her dating guru slash guy whisperer Alex
(Justin Long), and he informs her that unless her date is going off to
some satellite-less Third World country, there's no reason the guy
shouldn't be able to call her. Blown off before the night was even over.
Cher (Alicia Silverstone) spends a lot of time trying to hook up with the new guy Christian (Justin Walker),
sending herself flowers and gifts at school. She finally peaks his
interest enough to get him to come over, and once she has him on her
bed, he rejects her attempts at playing footsie and her classic
hair-flip come-hither move. It is then that the audience realizes that
Christian is actually gay.
Since Andie (Kate Hudson) is trying to get Ben (Matthew McConaughey)
to dump her, she tricks him into going to The Garden to see a
Celine Dion concert under the guise of taking him to see a Knicks game.
And at one point she even makes him eat a disgusting vegetarian meal while she
sneaks to the kitchen to eat meat and watch a game with the cooks.
#11 // WORST DATE ACTIVITY: No Strings Attached
Basically, Emma (Natalie Portman) invites Adam (Ashton Kutcher) to a funeral.
#10 // MOST PATHETIC BEHAVIOR ON A DATE: What's Your Number?
Ally (Anna Faris)
tries to reconnect with a few old boyfriends to see if any of them were
worthy of a second shot. One of them happens to be British (Martin Freeman),
and she happen to have pretended to be British when she met him. I'm
not quite sure how she managed to keep that charade up for so long, but
as they reminisce, she gets so hammered that her light, airy, princess, faux-British accent morphs into My Fair Lady, and then she goes "full Borat."
#9 // WORST YOUNG-LOVE HEARTBREAK: New Years' Eve
Hailey (Abigail Breslin) goes above and beyond to meet Seth (Jake T. Austin) in Times Square for their midnight New Years' Eve kiss. But when she gets there, one of their classmates grabs him and plants one on him, stopping her dead in her tracks.
#8 // MOST AWKWARD SEXUAL ADVANCE ON A DATE: She's the Man & Just One of the Guys
female leads in these films dress in drag to gain the same respect that
men do, and inadvertently attract women in the process. When they agree
to go on double dates with girls for the guys they're interested in,
the ladies get a little frisky, which can become a little uncomfortable
when what they're reaching for is actually a rolled up sock.
#7 // WORST ACCIDENTAL SEXUAL ADVANCE ON A DATE: The Ugly Truth
Abby (Katherine Heigl) and Colin (Eric Winter)
go watch a baseball game as their first date. At some point, she drops a
drink on his lap and begins to frantically clean it up. Of course,
friction down under is usually a bedroom activity, so not only does she
arouse him, but they're caught on the JumboTron and it looks like they're
doing something really dirty.
#6 // WORST DISCOVERY ON A DATE: Valentine's Day
Jason (Topher Grace) and Liz (Anne Hathaway)
have been dating for a few weeks and he doesn't realize it's V-Day
until the day of, so he tries to make last-minute plans to impress her.
Nothing really goes right, their table is super close to an arguing
couple, and she keeps disappearing during the meal. He discovers when
she's gone too long that she's actually been on the phone with clients.
Not business associates, but horny men who require her to use a series
of accents and role playing characters to arouse them, because—wait for it—she is a
freelance phone-sex operator. Surprise! Happy Valentine's Day!
During a cooking lesson, Alex (Will Smith)
taste tests some of the food and has a severe allergic reaction that
makes his face swell up like a puffer fish—and that's after the date
where he kicked her in the face while they were jet skiing.
#4 // WORST KISS ON A DATE: I Love You, Man
Peter (Paul Rudd)
is desperate to make guy friends before he gets married so he can pick a
best man, so he agrees to go on a bro-date with his mom's friend's son
Doug (Thomas Lennon). Unfortunately, he learns a little too late
that the guy is gay and he was under the impression that it was a
date-date, and plants a big wet one on his lips. Awwwwwkward!
#3 // WORST END TO A DATE: Easy A
Olive (Emma Stone)
sort of starts a business helping nerds who don't want their classmates
to think they're virgins. In exchange for pretending they made it to a
few bases with her, they give her discounts and gift cards. Then one
day, her ex-bff's crush asks her on a date, and she's all too excited to
finally get romanced. Their date has to end early when she realizes her ex-bff is at the restaurant, but instead of trying to continue the date
elsewhere or even driving her home, he whips out a gift card and asks
for sex. She's utterly crushed, realizing she's become the high school hooker.
#2 // MOST HUMILIATING DATE-THAT-NEVER-WAS: Never Been Kissed
During a flashback, we get to see what happened when the hottest guy in school asked Josie (Drew Barrymore) to the prom. Instead of driving up in a limo, he drove by, hung out of the sun roof, and egged her.
Blind Date & Date Night
In one film, Walter (Bruce Willis) goes on a blind date with a woman named Nadia (Daryl Hannah) only to discover a little too late that when she drinks too much she gets so wild she needs to be wrangled like a toddler high on Halloween candy. And in the other, Phil (Steve Carrell) and Claire (Tina Fey) are a married couple who decide to salvage their date night by stealing someone else's reservation, unaware that they're impersonating criminals who are wanted dead. They go from getting held at gunpoint in an alley to having to blend in at a strip club.