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Bad Date Scenes

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Valentine’s Day is drawing near, and that means an awful lot of people are feeling the pressure to put together a magical, romantic date night that will fan the flames of love. Or at least get them to second base. But not to worry. No matter what happens, it’s not likely to be anywhere near as painful as these classic movie scenes of dates gone awry.



Woody Allen and Dianne Wiest have a hilarious train wreck of a first date in “Hannah and Her Sisters,” one of Allen’s best films. She’s interested in punk rock and drugs, while he’s all about jazz piano and The Great American Songbook. He ends the date by telling her: “I had a great evening. It was like the Nuremberg trials.”



This one is a tragically bad date – because Dustin Hoffman is intentionally trying to show Katharine Ross a horrible time, at the request of her mother. He ignores her, belittles her and finally takes her to a strip club, forcing her to sit near the stage. The thing is, he really likes her, and that fact makes her slow transition from excitement to humiliation all the more heartbreaking.



You’d think a blind date with Kim Basinger would be a good thing, right? Well, not when you have an ex-boyfriend stalking you and you discover your demure date becomes a wild woman after a few drinks. Poor Bruce Willis.

BABY MAMA (2008)


The great Tina Fey nails it in her bad date scene in “Baby Mama.” Here she is at a nice restaurant with a guy, and rather than ease her way into getting to know him better, she jumps right to the heart of the matter. Marriage may or may not happen some day, she says, but “I’m 37. I want a baby NOW.” The guy’s reaction – excusing himself so he can hail a cab – is perfect.



Before Harry and Sally (Billy Crystal and Meg Ryan) get together, they try to set each other up with their best friends (Bruno Kirby and Carrie Fisher). Naturally, it doesn’t go as planned. My favorite part is when the only conversation Crystal and Fisher can muster has to do with the fact they both grew up in New Jersey.



Although Jack Nicholson and Helen Hunt are an incredibly unlikely couple in this film, their attempt at a traditional date is highly entertaining. Despite all odds (and a clothing emergency), things are going pretty well until Jack reveals something that he should have kept to himself. Check, please!



Similarly, the first date between Jane Adams and Jackie Earle Haley is doomed in the drama “Little Children.” This one is not for the squeamish. Haley’s character is recently out of prison for exposing himself to a minor, and Adams is a lonely woman looking for a shred of kindness and companionship. It doesn’t go well.



This one is my favorite. It’s by far the best thing in a truly mediocre movie about divorce and parenting, starring Paul Reiser. About midway through the movie, single dad Randy Quaid finds himself on a date from hell with Janeane Garofalo, who has some … issues. The two are great together, especially Garofalo, as they launch barbs at each other at an Italian restaurant. I’d almost forgotten how good Quaid was before he went nutjob.

But here I am again, monopolizing the conversation. What are YOUR favorite bad date scenes?

Great Breakup Scenes

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Breaking up is never hard to do in Hollywood. Movies and TV shows are full of characters going through breakups of all sorts. Here are some examples we here at The Jimbo List find particularly memorable.

LOUIE (2012)

Full disclosure: this scene from Louis C.K.’s brilliant TV show is the inspiration for today’s List. Like everything else in the series, it’s original and realistically off-kilter. Louie and his not-really-a-girlfriend April break up almost by osmosis. She has to do all the talking, putting into words all the complicated feelings Louie has but can’t say. This guy is a genius.


Let’s proceed to another New York City genius, Woody Allen. His films are brimming with breakups, plus a line about them that will live on forever in film history. In “Annie Hall,” he says that a relationship is like a shark. It has to keep moving forward in order to survive. “I think what we got on our hands is a dead shark,” he tells Diane Keaton.


I’m not certain about this, but I’m guessing Jason Segel is the first guy to do a movie breakup scene with full-frontal male nudity. Daring, but also smart. His character, who is getting dumped by Kristen Bell, is naked in every way.


Angela Bassett shows us the only thing you can do in a movie when your husband leaves you for another woman: you blow up his car. That way, there’s no ambiguity about the breakup.


This Oscar winner for Best Picture is a perfect example of the kind of stoic, do-what-you-have-to-do spirit that was such a part of American life – even in breakups. Dana Andrews is a returning World War II veteran with a menial job and a cheating wife. Then he meets Teresa Wright, the daughter of another veteran. They fall in love, but the father tells Andrews to do the right thing and leave his daughter alone. And that’s what he does, in a terse, no-whining breakup scene.


“Seinfeld” featured many great breakups during its run, but my fave is when Gwen dumps poor George with the line, “It’s not you, it’s me.” This infuriates George, not because he got dumped, but because he insists he “invented” the it’s-not-you-it’s-me strategy.


Not many people have seen “The Foot Fist Way.” It’s a weird, weird film, but features a fearless performance by the hilarious Danny McBride. He’s a martial arts instructor with a whole mess of problems. In one scene, his unfaithful wife asks him to take her back. He responds by urinating on his wedding ring.


Is it any surprise that Dustin Hoffman and Meryl Streep have one of the most painful, incredible breakup scenes of all time? Every one of their scenes together in “Kramer vs. Kramer” is amazing. Here, Streep’s nerves, determination and fear are all right on the surface, as are Hoffman’s initial arrogance, denial and frustration.


Aptly, this movie’s take on the oddly anti-social underpinnings of Facebook begins with an Aaron Sorkin verbal assault of a breakup. Rooney Mara and Jesse Eisenberg are terrific handling Sorkin’s intricate dialogue. It’s like watching a prizefight.

NETWORK (1976)

Let’s not forget the other “Network,” while we’re at it. William Holden is a network news exec who leaves his wife for Faye Dunaway, a ruthless network programming exec. When he gets fed up with Dunaway, he tells her she’s “television incarnate, indifferent to suffering, insensitive to joy.” That sort of line was devastating in the ’70s.

500 DAYS OF SUMMER (2009)

It was fun while it lasted, but eventually Zooey Deschanel has to lower the boom on Joseph Gordon-Levitt. She does it by invoking doomed punk rock couple Sid and Nancy. Gordon-Levitt is stunned to learn that he’s Nancy. Yikes.


Meg Ryan was the queen of the amicable movie breakup, wasn’t she? Here, and in “You’ve Got Mail,” she calmly, earnestly sits the guy down and explains that the organization has decided to make a change. Bill Pullman is the target in “Sleepless,” and he reacts with a sad dignity. But hey – she’s got to get to the Empire State Building, pronto.

CLOSER (2004)

“Closer” is like a sampler of breakup scenes. The whole cast – Natalie Portman, Jude Law, Julia Roberts and Clive Owen – gets at least one good breakup to chew on during the proceedings. Director Mike Nichols has covered some of this bitter relationship territory before, in classics such as “Carnal Knowledge” and “Who’s Afraid of Virginia Woolf?” This one isn’t quite in the same league with those.


To me, the scene where Woody Allen ends his relationship with young Mariel Hemingway is utterly heartbreaking. It’s a decidedly creepy relationship to begin with, of course. But Hemingway’s tears, and her quiet pain, are deeply moving.


Best breakup scene. Best breakup line. It comes at the end of a long, eventful story, but it’s worth the wait. People have been quoting it, and Clark Gable’s delivery of it, for more than 70 years.

I know there are plenty of other good examples out there. Which ones are your favorites?

5 New/Old Movie Double Features

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Sometimes when you watch a movie, you get a sudden, happy flashback to another film you enjoyed years ago. It might have a similar theme, locale or situation – but it makes you want to see that old film again for comparison’s sake. Here are five such double features that have come to mind recently.




They’re both smart, they’re both funny and they’re both romantic comedies about best friends who become more intimate. I greatly enjoyed Jennifer Westfeldt’s “Friends With Kids,” which features a winning cast that includes Adam Scott and Maya Rudolph. My one problem was its unbelievably clunky ending. It seemed to grasp at elements from several earlier films – including “When Harry Met Sally.” That’s a movie I liked a lot, as well. Its ending was schmaltzy, but it worked. And it had classic performances by Billy Crystal and Meg Ryan. But something it didn’t do was bring children or grandparents into the mix; Harry and Sally existed in this sort of unrealistic bubble.




Here are two quirky, wonderful films. “Salmon Fishing” is about a crazy plan to bring salmon fishing to a desert; “Local Hero” is about an oil company attempting to purchase a town in Scotland for a refinery. Different as those stories are, they share a common sensibility. They feature isolated main characters (Ewan McGregor and Peter Riegert) who find something magical and invigorating during a business trip to another country. They also encounter charismatic authority figures (Amr Waked and the great Burt Lancaster) and a host of oddball supporting characters.




Times and technology may change, but young married couples will always need to negotiate their personal version of the American dream. Albert Brooks explored this theme with hilarious results in “Lost in America,” one of the funniest films ever made. He turns the words “nest egg” into something sublime and his scenes as a school crossing guard are brilliant. “Wanderlust” offers smart performances by Paul Rudd and Jennifer Aniston in their own journey of discovery, via a hippy-dippy commune. It’s not on a level with “Lost in America,” but it has very witty moments and a solid supporting cast.




Bear with me on this one. You’ve got two branches of the action movie genre here, but they both feature one guy tasked with bringing another guy to justice. That other guy, meanwhile, is trying to get into the hero’s head and find a way to escape. A road trip and lots of bonding ensues. In “Safe House,” Denzel Washington is a tough, rogue spy being escorted to authorities by young spy Ryan Reynolds. Washington is rakishly sly and intimidating, and the film boasts all the quick-cut, hand-to-hand combat scenes that today’s audiences crave. Yet its greatest strength is the easy chemistry between Washington and Reynolds. The same is true for action-comedy-buddy movie “Midnight Run.” Robert DeNiro is a bounty hunter taking embezzler Charles Grodin to Los Angeles. Grodin masterfully nags, jokes and irritates tough guy DeNiro into submission. Again, chemistry is the key.




Full disclosure: This one is based on sage observations by friends of The Jimbo List. “The Hunger Games” and “Battle Royale” are both about dystopian futures in which teens are forced into deadly battle with each other by authoritarian governments. The difference is cultural. “The Hunger Games” takes place in a version of North America, while “Battle Royale” is set in Japan.

So that’s five. Now let’s hear your suggestions for new/old double features!