Yawn and Reach

The old yawning trick. Watch his arm.

—Hellboy

This is when a guy puts his arm around a woman's shoulders while pretending to yawn, in an attempt to look smooth and nonchalant. This trope only applies when this is a romantic gesture, rather than a comforting thing. If they're boyfriend and girlfriend, this is widespread—in TV and in Real Life. If not, hilarity is likely to ensue.

Examples of Yawn and Reach include:

Comic Books

In the Immortal Iron Fist comic book, the Boisterous Bruiser character Fat Cobra attempts to do this to the martial artist Tiger's Beautiful Daughter as they're sitting next to each other at dinner. For his troubles, she stabs him in the hand with one of her hairpins.
Pulled off successfully in American Born Chinese. Hilarity still ensues, though, as the boy realizes that by draping his arm over his love interest, he had rubbed some of the (very visible) soap bubbles on his hand onto her shoulder, and spends a good deal of time agonizing over whether she noticed or not.
Mac Gargan/Venom tries to pull this on Daken in Dark Avengers, but chickens out at the absolute last second. Daken responds by reaching between Mac's legs... and taking a handful of popcorn from the bag Mac is holding in his lap.

Film

Lampshaded in the Hellboy movie.

(as they watch Hellboy's crush, Liz, and John sitting on a bench)
Kid On Rooftop: Look at him! He's yawning! He's bored!
Hellboy: Yeah, yeah, the ol' "stretch-and-yawn" trick. Watch and learn, kid.

Grease, in the drive-thru scene (it fails).
King Kong Lives... done by Kong to Lady Kong. This somehow manages not to be the dumbest moment in the movie.
Doug from A Night at the Roxbury does this. The girl moves his hand from her shoulder, to her breast.

Literature

Lois McMaster Bujold calls it the "I'm-just-resting-my-arm-on-the-back-of-this-chair technique". It's her young-lothario character, Ivan, that does it, in Cetaganda.
In The Hob's Bargain by Patricia Briggs, Caefawn the hob sits next to Aren and rests his tail on her other side. She moves it, only for him to slowly work it over back to her other side again.
Subverted in Kushiel's Legacy. Phedre reaches for a knife on a nightstand, to assassinate Waldemar Selig. Her movement wakes him, and so she plays it off as this trope, instead.

Live-Action TV

The Ur Example of this was Marcia's boyfriend doing this to her on The Brady Bunch.
In the Ugly Betty episode "Something Wicked This Way Comes", Gio has to pretend to be Betty's boyfriend. When he puts his arm around her, his acting becomes a little too convincing for Henry.
iCarly: Freddie uses one of these to try and bust a move on Carly in iDon't Want to Fight. Freddie fails, not just because he's Just Friends, but because he's interrupted by a toilet flushing (Spencer saying goodbye to a goldfish he killed). He also arguably started off too far away for a really effective move.
Richie attempted this on Happy Days, but he needed to use a certain arm, and so he actually asked the girl to switch places before attempting it.
Also happened to George from Seinfeld. It failed
Howard Moon does this in The Mighty Boosh to Precious Lilywhite, who is a woman made out of a coconut and some sticks. Yes, really, and it's quite charming, too.
- "He's a good influence on me, actually."
Seinfeld had a variation that served the same basic purpose: stopping-short. While a man's driving a car with a woman in the passenger seat, he brakes suddenly and puts his arm out in front of her, supposedly to make sure she doesn't slam into the dashboard, but actually so her breasts will slam into his arm instead.
From That '70s Show, Donna does it to Eric.
Used and lampshaded in Herman's Head when Herman is dating a TV star who had the trope used on her character.

Newspaper Comics

A very early Doonesbury has Michael pulling this on JJ, successfully. He also tries to put his hand on her leg but manages to get a handful of ice from her soda instead.
Garfield with Jon it fails.
Knute teaches Gunther about the proper Yawn And Reach technique in a Luann arc.

Video Games

In the first Sims game, when you sit on the couch with someone and select...I think it was "cuddle", this is what happens.
- This returned as a new interaction called "make move" in The Sims 3 Late Night expansion.

Web Comics

Rule number Two in The Wotch. Used more successfully later.
[1]
Used in Misfile here.

Web Original

The infamous "yawn technique" from Lonelygirl15, as memorably demonstrated by Bree in "My First Kiss". Also seen in "Rockin' the Boat" (probably as a Continuity Nod or in-joke)
Crossing over with Captive Date, The Nostalgia Chick tries to do this with Todd in the Shadows when she has him tied up at her house.

Western Animation

Used in The Simpsons where Homer tries to teach Grampa this technique, complete with an explanatory song.
- Also used with Principal Skinner and Patty, though she catches on and tells him off when he does it.
- And in the episode where Homer and Marge tell the story of how they met as children, except it's deconstructed as it causes Marge to worry that she's boring Homer.
- Also in the Treehouse of Horror episode "Starship Poopers" with Kang attempting to crossbreed with Marge.

Kodos: Initiate fertilization procedure.
Kang: (Yawn and reach)

Used by Fry toward Leela in Futurama with zero success.

Leela: Take it off or I'll break it off.

- Kif does this to Amy with success.
Dale Gribble tells his son Joseph to do this on a girl he likes (Connie) when she is tutoring him in King of the Hill. "Don't forget to yawn-and-stretch!"
Used in Happy Tree Friends when Nutty imagines dating a gumball machine and does this when he is in movies with the said gumball machine.
In a Family Guy episode, when Peter wants to be a redneck, he does this... with Meg.
Teenage Mutant Ninja Turtles (2003) has a boyfriend/girlfriend example in the episode "The People's Choice", where Casey does it to April while hanging out at his grandmother's farm.
In The Spectacular Spider-Man's first season finale, Flash Thompson attempts this on Mary Jane Watson, with predictable results.
Jonesy on 6teen explains this to Wyatt when giving him his dating training.
- Darth Mall also attempted this on Nikki, only to fail spectacularly.
Parodied in Kaeloo, when Mr. Cat pulls this manuever on Quack-Quack on a couch in order to punch him in the face.
In Mickey Donald Goofy : The Three Musketeers, Mickey pulls this move on Minnie during their Falling In Love Montage, although we don't actually see/hear him yawn.

Real Life

This happens more than it ought to in Real Life, usually in what in fiction would be close to a Lampshade Hanging between friends- accompanied by an overacted 'yaaaaaaaawn...'
Dave Barry once described doing this on a date as a youth. The joke comes as he says that his arm went numb because he had to keep it a molecule away from her actual body.