Awkward Movie Dates: Worst On-Screen Romantic Moments From 'Reality Bites' To 'Annie Hall'

Posted: 04/17/2012 9:27 am Updated: 04/19/2012 5:14 pm

Annie Hall Awkward Date

This Friday is the 35th anniversary of "Annie Hall." The Woody Allen favorite, which won Best Picture in 1977 -- beating out "Star Wars" -- made "The Sorrow and The Pity," spider killing and neurotic rants a necessary part of romance.

But "Annie Hall" also goes down as a pioneer of tackling the awkward first date (and thus holds the copyright for the funniest subtitles ever). So, in honor of the movie's anniversary, we put together some more awkward movie dates for your cringe-worthy enjoyment. La-di-da!

WATCH:

  • "Kissing Jessica Stein"

    2001's "Kissing Jessica Stein" briskly rounds up the horrors of dating through a series of bad first encounters. Note to guys: Never act like this on a date.

  • "When Harry Met Sally"

    "When Harry Met Sally" beautifully articulated the potential pit falls of setting your friends up. (Also, Meg Ryan's facial expressions during this dinner are priceless.) But we all know that in this 1988 classic, everything happens for a reason.

  • "Baby Mama"

    If only Jack Donaghy were there to help Tina Fey through her I-want-a-baby-now speech in "Baby Mama." As she says, "It's too much for a first date, isn't it?"

  • "There's Something About Mary"

    Arguably one of the grossest dates in movie history, this scene in "There's Something About Mary" serves as a reminder that your night out could always be worse.

  • "Reality Bites"

    Winona Ryder has mastered the art of adorable awkwardness in 1994's "Reality Bites." Ladies, take note.

  • "Groundhog Day"

    Even though Bill Murray has time on his side, his merry-go-round date with Andie Macdowell always seems to miss the mark. Oh, well. To world peace!

  • "The Graduate"

    Yes, Dustin Hoffman personified awkwardness in "The Graduate," but can you blame him? At least everything ended up working out for him and Mrs. Robinson's daughter, right?

  • "Garden State"

    Natalie Portman might have regained her originality during this scene from "Garden State," but she did so at the expense of Zach Braff's feelings -- and a potential make out sesh.

  • "Rushmore"

    One sure fire way to ruin a dinner: undermine a doctor and confess to your teacher that you're in love with her.

  • "Annie Hall"

    While we may not all share his macabre point of view, Woody nails the first date jitters in 'Annie Hall."

FOLLOW MOVIEFONE

'FONE FINDS
This Friday is the 35th anniversary of "Annie Hall." The Woody Allen favorite, which won Best Picture in 1977 -- beating out "Star Wars" -- made "The Sorrow and The Pity," spider killing and neurotic ...
This Friday is the 35th anniversary of "Annie Hall." The Woody Allen favorite, which won Best Picture in 1977 -- beating out "Star Wars" -- made "The Sorrow and The Pity," spider killing and neurotic ...
Filed by Jessie Heyman  | 
 
 
  • Comments
  • 45
  • Pending Comments
  • 0
  • View FAQ
Post Comment Preview Comment
To reply to a Comment: Click "Reply" at the bottom of the comment; after being approved your comment will appear directly underneath the comment you replied to.
View All
Favorites
Recency  | 
Popularity
Page: 1 2  Next ›  Last »  (2 total)
10:10 AM on 04/24/2012
my buddy's mother-in-law brought home $17438 last week. she been working on the laptop and moved in a $418100 house. All she did was get lucky and put into use the directions uncovered on this website NuttyRich.com
04:55 AM on 04/23/2012
I have not seen any of these movies.....probably a good thing too!
02:06 AM on 04/23/2012
The scene form "The Graduate" is terrific, but it hardly qualifies as a "date", good OR bad.
11:57 PM on 04/22/2012
Annis AHall beating out Star Wars, Was a joke, and shows the people who vote on the academy know nothing about movies, It is voting for someone who can help You, or a friend
10:52 PM on 04/22/2012
Annie Hall winning an Academy Award was one of the biggest tragedys in movie lore. What a boring drawn out movie. My wife and I both wanted to leave 1/2 hour into it. And to think it beat out Star Wars for best movie. That shows the hollywood agenda mentality. They were in love with Woody Allen.
10:42 PM on 04/22/2012
Yeah, I have to agree that spider / Buick line has always been one of my favorites, too. Makes me laugh just thinking about it (and I've even used it myself more than once!). Talk about awkward, does anyone remember Candace Bergen busting out in song in front of Burt Reynolds in Starting Over?? Flippin' HILARIOUS!!!! Funniest ... and most AWKWARD thing ... I've EVER seen!!!
HUFFPOST SUPER USER
SuperDaveOsborn
09:46 PM on 04/22/2012
Guys just don't get it - and perhaps why even handsome men settle for the Broom Hildas of the world, and be it a script in a movie or the real thing, as long as men continue to have no deep inner game and project that wussy quality that girls want to vomit over, the death march to unhappiness, (for both genders) continues.

Women KNOW what men want from them & when it comes to approaching women, as long as every guy does exactly what other every guy does, it's a wonder that people ever hook up !

So listen up guys: " WOMEN ARE THE MOST INSECURE CREATURES ON THE FACE OF THE PLANET, and the prettier they are that much more so ! And "instinctively" they want an Alpha Male, so a projection of confidence, arrogance and cocky funny humor is the way to go, and this because "Opposites Attract" - and so if she's insecure, will she be ATTRACTED to someone who is also ?

In the beginning, NEVER offer to buy a woman dinner, nor rush out for flowers; but rather make her want to spend time with you, by being mysterious & funny and watch what happens .......
10:55 PM on 04/22/2012
Well said, that way that good looking woman will fall in love with a funny, mysterious LOSER! which most of them do, and usually he has either NO job or a crap job. But this is what they want, instead of that intelligent looking, possibly "geeky" guy who is sincere and will treat her with dignity and has a REAL job. Go figure.
photo
Savine
The course of true love never did run smooth. WS.
11:11 PM on 04/22/2012
You are both right in a way. Women do like funny, smart guys with riveting personalities. They also like guys who treat her with dignity and have goals in life.

It's a balance. What they don't like are guys that are bitter and hate women. =)
photo
HUFFPOST SUPER USER
elysianfields08
09:30 PM on 04/22/2012
This was a good movie for a while . Of course like everything in USA they beat it to death . Onr of few films I never want to see again . It was fun . Its now dumb
09:06 PM on 04/22/2012
That was the late great Bruno Kirby in the scene with Meg Ryan. My brother used to play baseball with him in NYC and thought of him as a great guy. RIP Bruno
08:35 PM on 04/22/2012
Meg Ryan's career ended when she went & cheated on her husband (Dennis Qualude), had to have that torrid affair with Russell Crowe, who promptly summarily dismissed her marriage-seekin' buttocks, yeah right, comin off Gladiator & he's gonna marry her, not gonna do it wouldn't be prudent...& her crown as America's princess was handed over to Sandra Bullock!
I do believe Meg Ryan is with John Cougar Mellenhead these days? maybe?

& as for Woody Allen!, WOW!, never thought he'd make it thru HIS grisly scandal, affair & marriage to his own adopted daughter, Soon Yi, but ya just gotta love Woody Allen, my personal fave is absolutely Sweet & Low Down!, hats off to Sean freakin Penn for that piece of work ;)
10:05 PM on 04/22/2012
So Woody Allen's affair with his adopted daughter was forgivable, but Meg Ryan's affair with a consenting adult (after a troubled marriage to a man with mental illness and drug issues) is the worst thing ever. Interesting.
12:15 AM on 04/23/2012
Absolutely not what I said at all, neither was a good thing for them(or anyone) to do and the price they will pay (or paid) is according to God, not for me or anyone to judge :) I am just sitting on the sidelines commentating like a common sweet potater should, making tasty remarks about these so-called "stars"... Russell Crowe suffered as well, he committed adultery with that married woman! Dennis Quaid is mentally ill?, seriously? I loved him in Dreamscape :) No cheaters will be tolerated, I believe Woody Allen was very despicable for engaging in his actions, however, he did marry the young lady and they are still together to this day, could that be why the public was more forgiving? We don't know, we just sit on the sidelines & watch & comment on blogs like this, for recreation :)
08:21 PM on 04/22/2012
I've never liked Meg Ryan
photo
HUFFPOST SUPER USER
Steve Sedlis
BM117 04-15-13 Boston Strong!
02:01 AM on 04/23/2012
She of the beehive hairdo and recurring role as the same person in different movies. But we also have the male version of the same look = Owen Wilson.
08:34 PM on 04/23/2012
well, I like Owen a lot better than Meg (you think it's because I'm a girl) lol, lol, seriously, don't ask me why, I have never liked the way she acts or her personality, she also made a movie with Tom Hanks, Tom, I like, he has not won a couple of academy awards for nothing; unlike her, he is a great actor.
photo
OC Surfer
A second is 30 nanoyears.
07:02 AM on 04/19/2012
THE most awkward movie about a date has got to be the Tom Noonan/Karen Sillas "What Happened Was..." from 1994. The whole movie is just their date, in her apartment in Manhattan.
12:00 AM on 04/19/2012
New Awkward Movie Dates: Worst Romantic Moments from The Five Year Engagement 2012 film hot scene video Here

http://x.co/jTrL
07:49 PM on 04/18/2012
Ah, Annie Hall. I just re-watched that the other day.

I needed the eggs.