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Top 10 Unorthodox Date Scenes

by Eric Melin on September 8, 2009

in Top 10s

Today’s Top 10 comes from Cameron Hawk, who previously submitted the excellent list Top 10 Uses of Pop Songs in Movies. If you have a list you’d like to contribute, email me at Here’s Cameron:

Dating—what a weird, mammalian concept. A lot of movies deal with the peaks and pitfalls of the practice because it is something everyone can instantly relate with. Usually, the high and low points are so  heartwarming or so awkward that they stay with us our whole lives. This list compiles what I believe to be scenes that present the dating ritual unapologetically, in all its naturally imperfect glory.

40-year-old virgin carell keener10. The 40-Year-Old Virgin (2005)

Steve Carell’s portrayal of the unexplainably celibate Andy is still my favorite performance of his. Andy’s personality is layered, complex, and at times strange, but never is it not apparent to us that he is a good soul. It might be harder for other characters to see, as they don’t have the direct access to his head that we do. This is what makes the film such a great study in humanity, and why people do the things they do or act the way they act. So obviously, in a film like this, the date scenes are going to be stellar. There are several memorable ones. However, the scene in which Andy finds out the hard way that he has never learned how to put on a condom has got to be the best of the bunch. After an amazing date with Trish (Catherine Keener), the two are feeling very comfortable with each other, and eventually the moment arrives. Right away, we can see in Andy’s eyes that this is the closest he has ever been to “the real thing”. He wants it to happen—it’s the right person, the right time, and she has plenty of protection. Unfortunately, Andy’s inability to properly apply a rubber soon leads to a large pile of unusable ones by the door, which are mistaken for already-used ones by Trish’s daughter Marla (Kat Dennings) when she and her boyfriend burst into the room. Right away, Marla assumes Andy is a sex fiend and that they have been having sex repeatedly throughout the evening. She couldn’t be more wrong, and these innocent misunderstandings make up the heart of the film, if not the heart of humanity itself.

Marla’s Boyfriend: Dude—teach me.

dunst elizabethtown phone9. Elizabethtown (2005)

The many outspoken detractors of “Elizabethtown” will first wonder why this movie is getting any kind of recognition on any kind of list anywhere—you all can just sit off to the side for now, or maybe head over to the TV room and pop in “Elizabethtown” again. When you watch it this time, try not to expect another “Almost Famous.” For that matter, try not to expect anything. For those of you who liked the film, or at least those of you who can muster a conversation about it without bursting out into random fits of cursing and self-mutilation, I am here to argue something—the scene with Kirsten Dunst and Orlando Bloom on the phone is one of the best first date scenes in film. Woah, back up—first date? How was that a first date, one may ask? They just talk on the phone for a long time, after all. Right? WRONG! These are the phone calls during which you really get to know a person. The fact that you are not there with them and cannot physically see them causes your other senses (and your imagination) to stand at attention. How does their voice sound? What does it sound like they are doing? It ends up being a window into these little details that we would normally take for granted. Drew (Bloom) and Claire (Dunst) talk for hours, and hours, with no signs of stopping, or wanting to stop. They even fall asleep while on the phone with each other. They are talking to each other the entire time they are driving to meet up, and even up until they are two feet apart. Now come on—we’ve all had phone calls like this. OK, so we don’t all drive and meet up with each other and get to see a southern sunrise, but remember, these are movies we are talking about here. Even still, after all the great conversation and the beautiful surroundings, Drew and Claire just part ways. When would have been the better time to seal the deal, if you don’t mind me asking?

Claire: Do you ever just think I’m fooling everybody?
Drew: You have no idea.

adams haley little children8. Little Children (2006)

This one is pretty disturbing, but I can’t go without mentioning it. Jackie Earle Haley plays Ronnie McGorvey, a convicted child molester who has recently been released from prison. Living with his mother, he is encouraged by her to meet people and go on dates. Instead, he spends most of his time scaring people out of the public pool, slithering around underwater with his goggles/snorkel combo. But Mon’s persuasions increase, and eventually Ronnie ends up going on a date with Sheila (Jane Adams). As the two begin to talk over dinner, some common ground is reached, and Sheila seems to think he is “nicer” than most of the guys she dates. Ronnie, too, seems to lighten up a little, even attempting to inject some humor into the conversation. Things continue to seem smoother and smoother on the drive home, and when Ronnie asks Sheila to pull the car over, one almost wants to entertain a notion that he is going to grab and kiss her, and the two will live happily ever after. But, Ronnie’s motives are more complicated than that—let’s just say he is less excited about her than he is about the kid’s playground off to his left. Man, there’s an awkward drive home.

Mom: There are four columns of lonely women in here, and only one of lonely men. The odds are on our side. Now why wouldn’t any of these women want to meet a nice person like you?
Ronnie McGorvey: I’m not a nice person.

carrey broderick medieval times cable guy7. The Cable Guy (1996)

For a movie that represents the early film careers of the likes of Ben Stiller, Jack Black, Owen Wilson, David Cross, Bob Odenkirk, and a score of others, “The Cable Guy” is pretty underappreciated. It may be kind of an obvious satire, but it still works—Chip (Jim Carrey), raised in front of the television, has spent his life assuming several different identities and posing as a Cable Guy, offering free cable to win friends. When he meets Steven (Matthew Broderick), something snaps, and Chip is convinced the two should be buddies. This leads to one of the great date scenes in the movie, which is actually a man-date—when Chip takes Steven to Medieval Times. Topped off with early bit parts from Janeane Garofalo as a “serving wench” (“There was no silverware in Medieval Times, hence there is no silverware at Medieval Times; would you like a refill on that Pepsi?”) and Andy Dick as the head knight (“Dude, get on the friggin’ horse!”), the scene builds to a hilarious duel between the two characters, in which Steven unwittingly pulls most of his energies from his frustrations with Chip. It’s a great performance from Broderick, who is running in fear of his life one moment, and attacking Chip with brute force in the next. Of course, the two end up kind of bonding, even though Chip still makes Steven uncomfortable. Chip’s attempts to win Steven’s trust eventually lead him to a restaurant where Steven’s ex-girlfriend Robin (Leslie Mann) is on a date with a hilariously jock-y Owen Wilson. When Wilson excuses himself to use the bathroom, Chip is waiting for him, disguised as a bathroom attendant. Chip then proceeds to physically assault Wilson in what has to be the most brutally funny bathroom beating ever. I still laugh hysterically every time Chip forces Wilson’s mouth around the hand dryer spout and says “You know, you really remind me of Dizzy Gillespie!”

Robin’s Date (Owen Wilson): [signaling the waiter] Excuse me, excuse me, pardon me, pardon me, pardon me, hey what’s the story with our chicken, man? Have the eggs had a chance to hatch yet? Maybe you can go check on it for me, my friend, if it’s not too much trouble for you. [the waiter walks away] Okay, I’m sorry to put you out. [Turns to Robin] See the attitude?

freddy got fingered green coughlan6. Freddy Got Fingered (2001)

Whether or not you like Tom Green or are moved by his humor, there’s a good chance you know about bits like “The Backwards Man” and “Daddy Would You Like Some Sausage?” But there is so much more to “Freddy Got Fingered.” Perhaps one of the most squeamish scenes in history, this date scene from Tom Green’s faux-art film is all at once brutal, hilarious, and completely original. As one of the two scenes that inspired this list, it really pushes the limits of not only where a movie can go, but where a date can go. Self-appointed loser Gordy (Green), in a previous scene, is found trying on one of his dad’s suits by his father, Jim (a hilarious Rip Torn). Gordy tells Jim he has received “a job at a computer company”, and that he also needs to borrow $50 so he can buy the necessary supplies—like, you know, “some pens, and that little thing that helps you draw a perfect circle.” Ecstatic, Jim tells Gordy to “take $100”, and later on takes his wife Julie (Julie Hagerty) out for dinner to celebrate. It isn’t long before Jim notices Gordy and his wheelchair-bound girlfriend Betty (the beautiful Marisa Coughlan) sitting at a nearby table, while Gordy is making a ruckus on a cordless phone he took from his father’s kitchen (“You’re fucking fired, Bob!”). The hilarity that ensues is beyond explanation, the kind that only Green could create for us. Later on, he canes her legs at her request. Green uses his movie to laugh at his audience (which explains why people hated it so much), and that’s pretty funny in itself. In the end, you’ll either love it to death, or want to kill yourself for watching it.

Jim: Wait a minute… You’re crippled.
Gord: Dad…
Betty: What?
Gord: Dad…
Betty: You got a problem with my legs?
Jim: No, you got a problem with your legs. It’s either that, or you’re just lazy.

spoonhauer.jpg5. Clerks (1994)

I had to cheat with this one a little bit, because the date itself never actually happens. But, I believe enough of it happened to put it on this list. Convenience store clerk Dante (Brian O’Halloran) finally meets up with ex-girlfriend Caitlin (Lisa Spoonhauer) after whining about her all day long, and she’s actually excited to see him. They talk about old times, and half-jokingly, Dante asks her out on one of his “famous dinner-and-a-movie dates”. Caitlin says yes, and the two get excited, like they seem to be getting those new-relationship-jitters for each other all over again. They agree to go home, get dolled up, and meet back at the convenience store. Caitlin returns before Dante, and decides to use the Quick Stop’s bathroom while she waits … seriously, has anyone not seen “Clerks”? SPOILER ALERT: She ends up screwing a dead guy that had died while masturbating in the bathroom earlier in the day (Dante gave him the porno mag!). By the time Dante returns, it’s too late—Caitlin is so traumatized she can’t even speak. But, wouldn’t it be more traumatizing to be cock-blocked by a dead guy? Poor Dante—he never did catch a break.

Dante: Call the police!
Caitlin: No, don’t!
Randal: Why?
Dante: Because there’s a stranger in our bathroom and he just raped Caitlin!
Randal: She said she did all the work.

punch-drunk love date watson sandler4. Punch-Drunk Love (2002)

The other film that that inspired this list, “Punch-Drunk Love” is the under-appreciated gem of the PTA catalog. Not like he is cast against type here, but Adam Sandler’s performance presents a remarkable restraint that shows us he can actually act. This makes his character, the extremely passive-aggressive (and that’s putting it lightly) Barry Egan, completely unlike his various other one-note comedy vehicles, which no doubt confused the large portion of the film’s audience who were expecting to see gay and fart jokes. Paul Thomas Anderson wrote the part especially for Sandler, and at no moment is it easier to see why than the infamous bathroom scene. Struggling to become his own man in the presence of his nine overbearing (and that’s putting it lightly) older sisters, Barry spends most of his time running his business of bathroom appliances and uncovering errors in sweepstakes programs for potential financial gain. Years of being mercilessly berated by his sisters has led to much repressed anger, causing him to feel the need to lie about everything. One of his sisters fixes him up with Lena (Emily Watson), who is super cute, and Barry takes her to a nice restaurant one evening. For awhile, things go splendidly—there is eye contact, and Barry actually makes a joke! But the inevitable mention of Barry’s erratic behavior (in this case involving the throwing of a hammer through a boat) and his sisters’ childhood exploits of him prove too much for him to take, and he excuses himself to the bathroom. Upon entering, he proceeds to beat the living piss out of it—the trash can, both stall doors, and the soap dispenser (oddly, the object he has the most trouble destroying) all get taken down. It’s the oddest, funniest moment in a wonderful little movie full of odd and funny moments, but it only gets better once the Restaurant Manager realizes it is Barry who has smashed up the bathroom:

Restaurant Manager: Sir, the bathroom was just torn apart.
Barry Egan: Um, yeah.
Restaurant Manager: Did you do it?
Barry Egan: No.
Restaurant Manager: You didn’t just smash up the bathroom?
Barry Egan: No.
Restaurant Manager: Well, who did?
Barry Egan: I dunno.
Restaurant Manager: Sir, your hand is bleeding.
Barry Egan: I cut myself.
Restaurant Manager: How?
Barry Egan: On my knife. (Silence.) What?
Restaurant Manager: Sir, your hand is bleeding.
Barry Egan: I know.
Restaurant Manager: I’m going to have to ask you to leave.
Barry Egan: Yeah, but I didn’t do anything.
Restaurant Manager: Sir, I’ve got no way to prove that you smashed up the bathroom—
Barry Egan: I didn’t do that. I didn’t.
Restaurant Manager: Look, I’m gonna have to ask you to go.
Barry Egan: OK. I didn’t—
Restaurant Manager: I’m gonna have to ask you to leave.
Barry Egan: Alright, please don’t do this to me.
Restaurant Manager: Sir, I’m gonna call the police.
Barry Egan: Alright. Can I just stay?
Restaurant Manager: Sir, I’m gonna crack your fuckin’ head open. Get outta here.

say anything 1989 cusack skye3. Say Anything (1989)

Cameron Crowe again! I’m telling you, the man knows relationships. I don’t just mean romantic ones, either; in fact, he is one of the best writers out there when it comes to pinpointing those subtle differences between friends, family, and lovers. Of course, we all know “Say Anything” is romantically oriented, but family relationships are a huge part of the film as well. Case in point—the scene where Lloyd (John Cusack) visits the home of his interest Diane (Ionne Skye) and her father James (John Mahoney) to have dinner with them and some of James’ friends and business associates. Some would argue that this is not technically a date, but I beg to differ—meeting parents is a huge part of the courting process, not to mention the fact that trying to impress them can be almost or just as complicated as trying to impress a love interest. It doesn’t seem to be a matter for Lloyd in this scene, however. He obviously wants the approval of Diane’s father, but his seemingly misplaced confidence becomes something more of an awkward assuredness as he begins to describe what he would like to do with his life. The answer he gives has become the quintessential response of all the other Lloyd Doblers and Ben Braddocks in the world, all those college grads out there who are constantly bombarded with this question. At some point in the scene, it becomes clear to us that Lloyd believes no one will ever be able to love Diane as much as he. Even with all the blank and disappointed stares coming from James and his guests, it comes across beautifully.

Lloyd Dobler: I don’t want to sell anything, buy anything, or process anything as a career. I don’t want to sell anything bought or processed, or buy anything sold or processed, or process anything sold, bought, or processed, or repair anything sold, bought, or processed. You know, as a career, I don’t want to do that.

sideways giamatti church madsen oh2. Sideways (2004)

Miles (an amazing Paul Giamatti) lives in the past, and his friend Jack (a likewise Thomas Haden Church) is constantly trying to yank him out of it, which is one of the many motives behind this little double-date scene in Alexander Payne’s classic. The memorable moments are almost too many to count—even the very first conversation outside the restaurant is priceless. What we get from there are peaks and valleys that go ever higher and ever deeper. Things seem to be going good for the two couples at first—Jack tries noticeably harder than Miles to keep the women engaged, but the fervent smiling and eye contact from beautiful Maya (Virginia Madsen) is not lost on Miles. Soon, however, Miles’ drunkenness gets the better of him, which leads him like a marionette to a pay phone in the back, and to one of the most painfully awkward drunk-dials in film. Seriously, any moment where you are blasted and calling your ex-wife is not a good one, and it makes Miles seem like even more of a hopeless case. But it also makes us feel for him, and in the end, his actions are those that require some balls. The date doesn’t end there, but it pretty much does for Miles—which is sad, because we know he wants to hit that.

Jack: Do not drink too much. Do you hear me? I don’t want you passing out or going to the dark side. No going to the dark side!
Miles: Okay!

Jack: If they want to drink Merlot, we’re drinking Merlot.
Miles: No, if anyone orders Merlot, I’m leaving. I am NOT drinking any fucking Merlot!

fast times ridgemont high backer date1. Fast Times at Ridgemont High (1982)

Does it really surprise you that Cameron Crowe has three entries on this list? (Crowe wrote the screenplay, but Amy Heckerling directed.) “Fast Times” is basically a montage of classic date scenes and teen fantasies (I know Phoebe Cates is coming to mind for some of you, as she damn well should.). There is one date scene that stands out, however, and rings hilariously true in its innocent awkwardness. In the scene previous to the first date between nerdy Mark Ratner (Brian Backer) and hottie Stacy Hamilton (Jennifer Jason Leigh), Ratner’s buddy Mike Damone (Robert Romanus) gives him a few pointers. “When it comes down to makin’ out,” Damone says, “put on side one of Led Zeppelin IV.” The next thing we hear, as Ratner drives with Stacy in the passenger seat, is the intro to “Kashmir”. Not only does Rat put it on at the wrong time—he puts on the wrong album entirely! These details and many more help this spot-on examination of awkward first dates, wonderfully realized by Cameron Crowe in his first screenplay. Halfway through dinner, Rat notices he has forgotten his wallet and has no way to pay for the meal. He decides to call on his buddy Damone to bring it to the restaurant, which Damone is wary of doing at first. (Though Damone’s reluctance to help Rat in his time of need should be considered foreshadowing, Ratner should not have called him in the first place, as it turns out to be nothing more than an invitation to cock-block.) Of course, while Rat is waiting for his wallet, he has to stall the date a bit, which he does simply by ordering more food and drinks. Soon, the couple’s table is full of restaurant debris, and Stacy looks shocked when Rat orders two more Cokes—right as Damone shows up to save the day! After narrowly escaping that predicament, Rat gets a piece of good news—Stacy’s parents happen to be out of town (her parents never seem to be home, in fact). She invites Rat to come inside, but he is too nervous to fire her up. He makes some excuse and says he has to go, leaving Stacy looking confused and unfulfilled. Through Rat, Cameron Crowe has given us something very valuable—an amazingly accurate blueprint of what NOT to do on a first date.

Mike Damone: I can see it all now, this is gonna be just like last summer. You fell in love with that girl at the Fotomat, you bought forty dollars worth of fuckin’ film, and you never even talked to her. You don’t even own a camera.

Eric is the Editor-in-Chief of and writes for The Pitch. He’s former President of the KCFCC, and drummer for The Dead Girls, Ultimate Fakebook, and Truck Stop Love . He is also Air Guitar World Champion Mean Melin. Eric goes to 11. Follow him at:

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{ 14 comments… read them below or add one }

1 Hai September 8, 2009 at 10:26 am

Good, creative list…. but youre forgetting Taxi Driver. Travis Bickle takes a girl to watch an adult movie on the first date and thinks nothing of it. She of course freaks out. Pretty demented stuff.


2 Eric Melin September 8, 2009 at 10:41 am

Yes! Good call, Hai. It was a very unique time in history. For a moment there in the 70s, porno was “hip.”
This is a great list, though, and I love that “Freddy Got Fingered” at least partially inspired it.


3 Bill Heinen September 8, 2009 at 11:39 am

great list, Hawks, really enjoyed it. I think your first entry got me thinking about Apatow a lot though, cause I kept recalling the classically strange and awkward dates from the great series Freaks and Geeks, and of course that breakfast date in Knocked Up where Katherine Heigl re-explains what she does for a living and Seth Rogen desperately asks for her number, especially that grimaced line, “we had fun…right?”


4 Angie Horner September 8, 2009 at 2:50 pm

Phoebe Cates was definitely in my mind…seriously, who wouldn’t want to make out to Led Zeppelin IV?


5 hellohawk September 8, 2009 at 5:13 pm

Hai–Dude, you are absolutely right! Guess I missed that one… Personally, I don’t get what all her fuss was about…


6 cleavy September 8, 2009 at 6:25 pm

Great list, Cam!


7 sborn September 9, 2009 at 3:09 am

Freddy Got Fingered scene. Classic!

It happens around 37:00


8 Eric Melin September 9, 2009 at 8:37 am

Scott- It’s nice to know that someone else appreciates FFF. Never would have pegged you for a fan. Oh, wait, Kill Creek was responsible for getting me into The Frogs. Makes perfect sense now.


9 ChrisKnudsen September 9, 2009 at 9:25 pm

Man, I love that Freddy Got Fingered scene. I am pretty sure that film will be in my top 10 of the decade along with 4 Months, 3 Weeks, and 2 Days, Yi Yi (did you watch it yet Eric?!? Haha), The Piano Teacher, and The Assassionation of Jesse James by the Coward Robert Ford. Since you are a real critic Eric, I expect you to put Freddy on there too and start the revolution.


10 MJ September 9, 2009 at 10:01 pm

Before Sunset?


11 hellohawk September 11, 2009 at 3:14 pm

sborn–THanks for the link!! Such a good scene.

Chris–That’s bold of you, but I love the fact that you fly the Freddy Banner high!

MJ–Sadly, I have not scene either of those movies…lame, I know. :{


12 Ross McG September 14, 2009 at 4:29 pm

man, I love top ten tuesday, although you lost me at ‘elizabethtown’
great save with Punch Drunk Love though – Lena and Barry are one of the great kooky couples, love it when they talk about how they want to smash each other’s faces in.
Cusack is prime awkward date gold, High Fidelity and Grosse Pointe Blank jump to mind


13 Cazart September 16, 2009 at 4:20 pm

He wasn’t even supposed to be here today!


14 John April 30, 2015 at 10:47 pm

I don’t mean to be rude. But after reading this post, I really wanted to say:


I was trying to look for a scene to inspire me to create a really good date scene for a short film and I am really short on time (well, long enough to reply in anger anyway).

So I spent most of my time watching the movie scenes on your (SHIT*[ Sorry ’bout that]) list. And not only did I not crack a smile, I didn’t even see anything good about their script or lines.

No offense Mr./Ms. Writer, but I’m really pissed off at wasting my time following your *(FUCKING) list.

We probably just have different tastes. Nevertheless, I apologize for this rudeness. I just had to let it out.

*Sorry for the not so nice English.


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