Deliberately Distressed Damsel

That Alice! She seems Too Dumb to Live. She picks up the Distress Ball and, like a true Damsel Scrappy, scores on her own team with it. And worse, she Looks Like She Is Enjoying It...

Well, in this case, she actually is.

While this character may look like a Damsel Scrappy at first glance, she's actually Obfuscating Stupidity. Whether she's pulling a Wounded Gazelle Gambit, playing Gambit Roulette, or just into this sort of thing, she doesn't get captured because she's weak, she gets captured because she wants to. She may even have the skills to get out of the scrape she's in herself if she wanted to. If this is the case, expect her to say Let's Get Dangerous at some point.

If she's getting captured because she's into it, she may be a case of Best Her to Bed Her. Expect her not to have much regard for Safe Sane and Consensual.

Compare I Surrender Suckers, and Aren't You Going to Ravish Me. Compare and contrast Decoy Damsel, which is a villainous variation on this trope.

Anime & Manga

 * Happened in Mobile Fighter G Gundam, with Tomboy Princess Maria Louise of France playing this role. It backfires SPECTACULARLY.
 * Rukia Kuchiki in the Soul Society arc in Bleach.
 * Orihime later tries to pull this in the Hueco Mundo arc, trying to act like she has joined the Arrancar to get an opportunity to reject the Hogyoku with her powers.
 * In the first episode of Busou Renkin, Tokiko leaves herself wide open, leading Kazuki to think she is just an Innocent Bystander. Nope. sh'e an Alchemist Warrior, and she was leading the Monster of the Week into a trap.
 * Surprisingly,  from Black Butler.
 * OTOH, it could also be a deconstruction. Unlike most girls that fit this trope,
 * Eiko from Hajimete no Aku tries this trope out to gain fame and fortune. She just ends up scaring off the people who put her in distress on accident.

Comic Books

 * Common Alternate Character Interpretation for Wonder Woman's appearing Bound and Gagged so often.

Literature

 * In Murder on the Leviathan, Renata Kleber gets into trouble on purpose in hopes of starting a Rescue Romance with the handsome protagonist, who seems to uphold chivalric values.
 * In Twilight, Bella thinks that she can psychically connect with her ex-boyfriend Edward if she gets an adrenaline rush, and purposefully puts herself in near-death situations to bring them on.
 * One of the parodies of it, New Moan, has Heffa (the parody of Bella) hoping Teddy (Edward) and Joe (Jacob) will fight over her, and tries to edge them into doing so.
 * In The Light Fantastic, Cohen the Barbarian, Rincewind, and Twoflower interrupt a druidic sacrifice, in the process rescuing the maiden who was about to be sacrificed. Said maiden is extremely indignant about the rescue, protesting that if it weren't for them rescuing her she would be "having tea with the Moon Goddess by now" and that they'd just caused "eight years of staying in on Sunday nights" to go "down the drain".

Video Games

 * A common interpretation for Princess Peach.
 * pulls this one off in Solatorobo. Unfortunately for her, Red gets there before her intended man and Hilarity Ensues.
 * Played with in The Legend of Zelda: Skyward Sword.

Visual Novels

 * in Umineko no Naku Koro Ni.

Web Comics
"Grace:"[discussing why a video game princess keeps getting kidnapped] Oh, it's like foreplay to her. She's kind of evil that way.""
 * in Girl Genius have a mix of high-end Obfuscating Stupidity and being just one little step behind the developing situation -- she may be ahead of most others, but never quite reaches the top perch.
 * Mentioned in El Goonish Shive to parody the Damsel in Distress:
 * Mentioned in El Goonish Shive to parody the Damsel in Distress:

Western Animation

 * Gender Inverted in the ThunderCats (2011) episode "The Duelist and the Drifter" Adventure Towns resident and habitual Distressed Dude the Drifter gets snagged on high fences three times, each time enlisting protagonist Lion-O's help to get down. This would be innocuous but for the fact that the Drifter possesses Not Quite Flight, and readily exploits these encounters to offer Adventure Rebuffs and unsolicited, passive-aggressive advice on Lion-O's own increasing problems while elaborately feigning disinterest.

Other

 * A very mild version of this is when a woman will drop her handkerchief in hopes that the man in question will pick it up and return it to her, which I've Seen A Million Times.
 * Played with in Monkey Business, where a woman drops a handkerchief in front of Zeppo, who pockets it and then drops one for her to pick up.