Innuendo Backfire

We were going to call this one "Solicitation Mistaken For Help", but this is snappier.

Basically, when a given character needs help (a place to stay, whatever), is approached by a prostitute who speaks with perhaps too much metaphor, and thinks her solicitation is an offer for assistance.

See also Platonic Prostitution and Accidental Innuendo.

Films -- Live-Action
"Simone: You looking for a good time?
 * In I Am Sam, Sam, a mentally handicapped single father, mistakes a streetwalker's mockery for a promise to help him raise his daughter. He is then arrested for soliciting her services.
 * Reversed in the movie The House Bunny. The policeman asks the Bunny to "blow" and... well... she doesn't quite understand that he's trying to check her alcohol content.
 * Crocodile Dundee does this. Then he knocks out the pimp when he insults the lady's honor.

Mick: Always looking for a good time! Name's Mick Dundee."

Jokes

 * There's old joke where a clergyman encounters a prostitute, she says "I'll do anything you can describe in 3 words for $50". He thinks about it for a while, and then says "Paint my house."
 * In one of his books, critic Joe Queenan's response to a (hypothetical) request of this nature was "do my taxes."
 * An engineering student approaches his friends at lunch one day riding up on a beautiful new bicycle. "Wow," says one of his friends, "where'd you get that bike?" The engineering student says, "Strangest thing. On my way back from class this morning, a gorgeous woman rode up on a bike, got off it, took off all her clothes and threw them on the ground, and told me, 'Take whatever you want!'" His friend nods sagely. "Good choice. Her clothes probably wouldn't have fit."

Literature

 * Discworld: Happens to men who approach the Guild of Seamstresses to have their socks darned.
 * In Guards Guards, a naive Carrot ends up living in a house of "seamstresses" due to this sort of misunderstanding. He mentions that his first night there one of the girls asked if he wanted anything, but they had no apples, so he said no.
 * Variant: In Feet of Clay, one character mentions that she was good at sewing, so she tried to join the Guild of Seamstresses.
 * Similarly, in Night Watch, there is an actual seamstress who is often confused for the other type.
 * In Reaper Man, Windle Poons, a newly resurrected zombie, is asked by a "seamstress" if he's looking for a good time. He's somewhat addled by the fact that he can see and hear clearly for the first time in decades, and accepts her offer without thinking about it. She runs away when she gets a good look at him, though.
 * In Interesting Times, Rincewind is approached by several beautiful, scantily-clad women who explicitly say that all of their men have died out and they need his help repopulating their island. However, due to years of living alone on a desert island, Rincewind's mind has deteriorated somewhat and he thinks they're offering to make him some mashed potatoes.
 * This happens in Don Quixote.

Live-Action TV
"Maggie: I'm not a hooker, you jerk. I'm your landlord."
 * Regenesis: Bob Melnikov, while in New York, goes in a back street to rehearse a speech he's about to give. A prostitute approaches him, and he doesn't understand for what reason. Fortunately for him, she's a Hooker With a Heart of Gold, and she does help him.
 * My Name Is Earl in the antique silverware episode. Randy was told to wait around the station and ask people if they had "the package"; a gay guy misinterprets this.
 * The inverse happens on CSI, when during her evaluation Catherine complains to Grissom that because of her hours, she hasn't had sex in at least half a year. "How can I help?" Gil asks, and has to clarify that he doesn't mean THAT kind of help when Catherine raises her eyebrow at him.
 * A possible slight variation -- in New Tricks, a prostitute approaches Brian and asks him if "you've got the time," in a fashion that leaves little doubt as to what she really means. Brian, however, assumes she's literally asking what the time is, and proceeds to tell her, resulting in a frustrating back and forth for the both of them until he storms off in exasperation and she gripes to one of her friends, "Why can't they just say if they're gay?!"
 * My Wife and Kids had a variation when the family goes to Las Vegas. Junior calls an escort service because he thought that it was a babysitter.
 * Frasier stops to give a woman standing in the rain a ride home, and he doesn't realise she's a hooker until just before he's stopped by the cops.
 * In another episode, two characters talk abour hiring a babysitter. One urges the other to carefully read the ads, because an ad's stating "has toys and willing to spank" doesn't means it's for a babysitter.
 * Inverted in the first episode of Northern Exposure, where Joel mistakenly believes Maggie to be a prostitute based on her offers of help. She does not react well to this, of course.


 * A hilarious subversion of this happens to Mateo in Benidorm. Mateo has to dress up in drag for a double date, and has to wait outside a bar for a few minuites. An undercover cop shows up, asking if s/he has a place to go. A lot of non-entendres later ("I have to get out of these pants" (They were itchy)), and he is promptly arrested.

Video Games

 * In Fallout 3, one of the joinable NPCs is Clover, an insane killer prostitute that you can own as a slave. When you strike up a conversation, she asks if she "can do anything for... or to... you." Sadly your responses are entirely on the lines of tactics and gear management.

Web Comics

 * Get Medieval: Asher, lost in medieval Avignon, has a girl come to him and offer him "a warm bed to spend the night in". Being a clueless nerd, he considers it an invitation to sleep at her place. The trope is subverted at a later stage, as when they meet again in different circumstances, she does offer her help.
 * In RPG World, this is how Diane ends up joining the party.
 * This page of Rob and Elliot is a magnificent aversion.

Web Original
"Kevin: "You...uh, looking for a jump?"
 * Played with in Episode 3 of Manwhores when a woman pulls up to Kevin, newly starting out his career:

Woman: "Depends on what kind you mean."

Kevin: "The, uh, sexual kind of course--unless, uh your car's actually broken. My car's right over there"

Woman: "What I need, I can't get from jumper cables."

Kevin: "Well I happen to not have any."

Woman: "Get in.""

Western Animation

 * The Simpsons: Subverted in the episode "The Cartridge Family". When Marge takes Bart, Lisa and Maggie to a motel because Homer is acting Trigger Happy, Bart is asked by a prostitute "are you looking for a good time?" He is (as always), but not in the manner she means, and Marge pulls him away before any Hilarity can Ensue.
 * The pilot episode of The Venture Brothers has a prostitute asking Hank and Dean if they're looking for some action. Being rather sheltered boy adventurers, they reply that they're always looking for action! And adventure!