Bad Date Scenes

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?