Affectionate Pickpocket

Some pickpockets execute their craft by avoiding all detection, and making sure their victims never register the fact that contact was made. Others prefer just the opposite. Affectionate Pickpocket is when a character tries to disguise picking someone's as an affectionate hug. Or even a Kiss of Distraction.

For instance, Alice spontaneously gives Bob a great big hug. "Did I ever tell you what a great friend you are?"

Oh, how sweet, thinks Bob. ...wait. Where's my wallet gone?

May lead to Give Me Back My Wallet or Hey, That's Mine!. Compare Five-Finger Discount and Percussive Pickpocket.

Examples of Affectionate Pickpocket include:

Anime & Manga

Nami from One Piece. Even as her goodbye from her home island has her taking everyone of her villager's wallets in a mad dash for the ship as a way of saying goodbye to them.

Fanfiction

Living with Danger: while she is staying at the Weasley's house after the Pack's adults have been arrested, Meghan hugs Mrs Weasley, telling her she is a great mum, and takes the chance to swipe her wand. She needs it to activate the Marauders' Map and find Hagrid.
Be the Sea Dweller Lowblood has two people do this with sloppy makeouts, in similar circumstances.

Film

The guy in Casablanca who puts his arms around visitors and warns them about thieves while robbing them.
Paco in Herbie Goes Bananas.
In The Meeting Place Cannot Be Changed we're told that Ruchechnik started his career in this manner - "mistaking" strangers for dear friends and filching their as he enthusiastically greeted them.
Maverick. Annabelle Bransford does this to Maverick twice in the same scene. The first time he notices and makes her give his wallet back, the second time he's so overwhelmed he doesn't notice and has to track her down later.

Literature

Fisk pulls this off enough times in the Knight and Rogue Series (in just the first book) that Michael gives up and simply makes holding on to the money Fisk's job.
In The Golden Nineties by Lisa Mason, one of the main characters meets a woman on the ferry into San Francisco, who claims to be seasick and asks if she can lean on him. After the boat docks, she disappears along with his wallet, and when he describes her to some locals, they identify her.
There's a story in Henry Peacham's The Art of Living in London (1642) about a tradesman whose wife's purse is stolen at the theatre, after she put it in her petticoats for safety. He asked why she didn't feel a hand, and she replied "I felt ones hand there; but I did not thinke hee had come for that."

Live-Action TV

Doctor Who, "Victory of the Daleks": Winston Churchill hugs the Doctor, and lifts the TARDIS key.
The Pretender, "Crazy": Jarod, doing time as an inmate in a mental asylum, hugs the orderly and thanks him for caring. The orderly immediately makes him give back his keyring. (After he leaves, we learn that the keyring was just a decoy theft, and Jarod also lifted something else.)
Leverage: Parker's mentor Archie asks her for his wallet back after they share an embrace. Given that he's the one who taught her to be a master thief, he'd probably be disappointed if she didn't steal it.
Alexis to her father on Castle as he was Bound and Gagged to a chair. She says he wouldn't respect her otherwise.
- On a later chapter, Beckett steals Castle's phone without him noticing. Being as he is, Castle can't help but ask her to do it again.
In a The Benny Hill Show sketch three men break out of prison; they reunite and give each other hugs, each of them robbing the others.
- In another Benny Hill sketch Robin Hood (Hill) has become the new Sheriff of Nottingham - Friar Tuck and Will Scarlet come to congratulate him and he lifts their money pouches as he hugs them, then sics the guards on them.
At the end of a Christmas Episode of Psych, a little girl/con artist thanks Shawn for helping her dad, and hugs him... and Shawn immediately asks for his wallet back.
Ames from Human Target.
Babylon 5, "Legacies": Ivanova has a heartwarming conversation with a Street Urchin that ends with the two of them clasping hands in a gesture of mutual sympathy... and the street urchin takes the opportunity to steal the commlink off Ivanova's hand, just to keep in practice.
Married With Children: Peggy has done this to Al, leaving him with "empty pants".
One episode of Arrested Development has Michael and Gob have a heart-to-heart talk which ends with a handshake and Gob saying "Thank you for your time." Later, Michael discovers that Gob stole his watch when they shook hands.
One episode of Nash Bridges ended with the title character sending away a young hoodlum. They hug just before the kid is to get on his plane. After that, the kid reveals that he stole Nash's wallet. After the kid returns it, Nash reveals he also stole the kid's wallet.
In Burn Notice, Samantha, Michael's ex-fiancée and thief will often pickpocket Michael as a way of flirting with him. He always asks for it back immediately after.
Subverted in JAG, an old friend of Harm's who works as a security consultant gives him a friendly handshake and slaps his back in a bar. Later, when Harm goes to reach for his wallet the friend pulls it out of his pocket and says that he could now get on any military base using Harm's stolen ID. Harm says he knew he'd been picked and opens the flap for his ID, which has a piece of paper saying "ARREST THIS MAN" instead of his credentials.

Newspaper Comics

Garfield has done this to steal food from people's pockets on at least two occasions.

Video Games

Played with in Baldur's Gate II: Imoen suddenly starts acting all love-struck and swooning around Keldorn, much to his horror (since he is Lawful Good, married, and old enough to be her father). After making him squirm for a bit, Imoen chuckles and gives him his ring back.
In Tales of the Abyss, Luke gets his wallet stolen when he first meets a "very friendly" Noir. Luckily Tear noticed before she left.
In Assassin's Creed II, Ezio learns early on how to pick pocket for extra cash, however this method becomes relatively useless as you progress in the game. Rose when you first met her, tries to pickpocket you.
Annah of Planescape: Torment tries this on your Player Character - typical of her overall Tsundere manner.

Web Comics

Sam Starfall from Freefall has been known to attempt this—but then, he's probably tried every thieving-technique in the book, and invented a few himself. (Of course, since everybody knows that he's a notorious thief and pickpocket, this particular technique doesn't work well for him.)
Something*Positive featured this exchange:

Jason: My wallet's on the dresser. There should be enough money in it to cover the bill and tip.
Aubrey: Don't worry about it, baby. I've got it covered. I palmed your credit card weeks ago.
Jason: Ah, yes. I do believe that was the sexiest pick-pocketing I ever fell victim to.

Strays: Going off to her room sort of affectionate.

Web Original

In Respect a Woman, Hunter uses a tender embrace as an opportunity to mess with Smoker:

Hunter: I'm stealing your wallet~
Smoker: That'll be a neat trick after I snap your neck.

Western Animation

The Simpsons, "Curse of the Flying Hellfish": Mr. Burns forces Grandpa to give up his key to the Hellfish fortune. Bart throws himself at Burns and wraps his arms around him, saying "Can I go with you to get the treasure? I won't eat much and I don't know the difference between right and wrong." This seems like a very in-character thing for Bart to do; but when Burns leaves (without Bart) Bart shows to Grandpa that he picked Burns's pocket, so now he has both keys needed.
Futurama:
- In the pilot episode, Fry and Leela put their hands together and Bender puts his hand in as well.

Fry: What's the matter with you?
Bender: I just wanted to be part of the moment.
Leela: Hey, he stole my ring!

- Bender gets sick; it turns out he stole Amy's watch and it's jammed in his gears. He pulls it out, returns it, and hugs her in apology. As he hugs her, he swipes her earrings.
Foster's Home for Imaginary Friends, "Foster's Goes to Europe": Right before finally getting to leave for Europe, Mac receives a hug from Madame Foster... only to discover by the time he and his friends are at the airport that his tickets are missing! The result: everyone is disappointed in a confused Mac (even poor Wilt!). Frankie comes in to see Madame, only to find her missing. Cut to Madame, with her friends in tow, not to mention Eurotrish, in the plane en route to Europe, chuckling over "getting what she needed from that hug". Certainly one of the most infuriating endings for what happened to Mac.