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     Mary Jensen/Matthews 
Played by: Cameron Diaz
  • Beware the Nice Ones: Mary is rather upset and gives Ted a well deserved The Reason You Suck speech when she finds out he's been stalking her for so long.
  • Dude Magnet: The entire plot of the film is based on the title character being one of these, although unfortunately only a particular type of men seemed to be attracted to her.
  • Girly Girl with a Tomboy Streak: Mary's into a variety of sports and enjoys beer and red meat.
  • Hair of Gold, Heart of Gold: Mary has blond hair and is quite a nice person.
  • Lust Object: All of Mary's suitors only show interest in her for superficial reasons. Healy spied on her getting changed and Norm was turned on by the sight of her in a nightgown. Woogie likewise went after her years later because he wasn't satisfied with his wife. Ted on the other hand actually showed interest in Mary as a person.
  • Nice Girl: She is a very kind-hearted person in general, including helping disabled kids as a living and letting her neighbor Magda live with her after her (Magda's) husband died, so she wont have to be alone.
  • The Prankster: Downplayed, but she tells Ted a few (made up)stories, knowing he's Super Gullible, only to say "I'm fucking with you, Ted" including saying she's really bisexual (although this may have been a test to see if he's homophobic, rather than just a prank.)
  • Single Woman Seeks Good Man: The reason Mary decides to be with Ted in the end — although she had seen some of his niceness on a date beforehand, it's not until he makes clear that he's fed up with being yet another stalker that she decides to be with him.
  • So Beautiful, It's a Curse: She has to deal with no less than five stalkers, suggesting something about her brings about this kind of reaction in people.
  • Static Character: Everything that Ted liked about Mary was maintained 13 years later. Just when it seemed like Mary would pick Brett over Ted, she reminded him of that time in high school when she mentioned being a Niners fan.
  • Unwanted Harem: Mary spends the bulk of the movie being chased by guys who spy on and manipulate her. Mary herself mentions Woogie being the worst of them, who began stalking her when she was still a teenager.

     Ted Stroehmann 
Played by: Ben Stiller
  • Almost Kiss: Ted's first kiss with Mary is postponed when Warren accidentally snags his lip on a fishhook.
  • Braces of Orthodontic Overkill: There's no parts that stick out of 1985 Ted's mouth or around his head, but it's still a pretty sizable set even for the 1980s.
  • The Chew Toy: Poor Ted gets mauled by a dog, nearly murdered by a hitchhiker, bludgeoned by a Rabid Cop, snagged on the lip by a fishhook, and beaten up by Warren. Oh, and then there's the whole zipper incident...
  • Dogged Nice Guy: One of the running gags of the film is everybody else using Ted as the butt of their jokes (up to the point that when Mary finally confesses she loves him Ted's immediate response is asking dejectedly if she's making fun of him) and out of all the stalkers he's the Only Sane Man.
  • Earn Your Happy Ending: After undergoing massive amounts of humiliation and pain, Ted gets to be with Mary after all.
  • Failed a Spot Check: It's revealed at the end that Ted's been failing this for quite a while, when the identity of "Woogie" is revealed: "Dom Wooganowski." [Does 'duh' gesture]
  • Groin Attack: Does this to himself by mistake when he accidentally gets his dick stuck in his zipper.
  • Heroes' Frontier Step: Ted standing up for Warren when some guy is about to beat him up is the first indicator that he's a good guy.
  • I Want My Beloved to Be Happy: Ted eventually realizes he doesn't have much moral superiorty over the other stalkers and ses Mary up with Brett again as he was the only one who treated her right. Mary ultimatelty chooses Ted based on this gesture (that and she's always been a Niners fan).
  • Mistaken for Masturbating: When Ted takes a leak while staring at a pair of doves out the window with a blissful look on his face, only to discover all too late that the house wraps around the backyard in such a way that he can see into Mary's room while she's undressed. What happens next ensures he won't be playing with himself for a while.
  • Nice Guy: Other than has inappropriate behavior towards Mary, he's a pretty decent guy.
  • Poor Man's Porn: On the advice of Dom, Ted masturbates before his big date with Mary, using some lingerie ads from a black-and-white newspaper.
  • Sexual Karma: Ted decides to quit being obsessed with Mary. Mary decides he's the one for her as a result. The movie ends with them finally having their first kiss.
  • Stalking is Love: Deconstructed. Ted is fully aware that his obsession with Mary is creepy and unhealthy, but she made such an impression on him that he just can't move on from her. Getting Healy to track her down failed as Healy was a scumbag who lied so he could have Mary to himself. As it turns out, all he had to do was bring her up while chatting with one of his friends, who told him everything he needed to know to find Mary in a more natural manner.
  • Super Gullible: Ted has a habit of believing anything people tell him. Everyone who knows him knows this, so they are always "fucking with him". Some of the deceptions are good-natured (like Mary saying she's bisexual), others downright mean (such as Dom telling him he has some disease and is dying.)
  • Unexplained Recovery: Ted gets two fish hook barbs through his cheek in a graphic scene but is none the worse for wear the next time he shows up.
  • Unwitting Instigator of Doom: Although it was mostly the result of Woogie's manipulations, Ted deciding to find Mary is what causes all of her past and present stalkers to come knocking at her door and for a brand-new one to be created.

    "Woogie" Spoilers Ahead 
Played by: Chris Elliott
  • Abhorrent Admirer: By the time he shows up in the present, he's lost whatever appeal he had in his youth, being a manipulative creep with a disturbing skin condition.
  • Amoral Attorney: Implied. His law firm was shown divulging the ramifications of a bus crash with numerous fatalities, with the main concern being how much this would cost their client.
  • Archenemy: Woogie is especially fixated on getting rid of Ted. Justified, as Healy's ruse wasn't going to hold up forever and Norm was operating under the radar.
  • Attempted Rape: Subverted at the end of the film. It sounds like Woogie is trying to rape Mary, but he's only trying to steal her shoes.
  • Big Bad: He was Mary's first boyfriend and he set Ted up with Healy so they could track down Mary after she tried to escape him.
  • The Chessmaster: Woogie advises Ted to hire Pat Healy to find Mary, advises Ted to contact her, drives Ted to Miami and then sends an anonymous letter to get both Ted and Pat out of the way, leaving him free to swoop in and steal her shoes all without Ted suspecting anything. Even his friendship with Ted appears to be an early move in his game.
  • Domestic Abuse: Turns out that Woogie got married, had two kids and his wife has no problem gratifying him sexually on a constant basis. He doesn't gives a shit about any of them, still being obsessed with Mary after so many years.
  • Evil Has a Bad Sense of Humor: Dom screws around with Ted by telling the latter that he's dying.
  • Evil Makes You Ugly: By the time Dom is revealed to be Woogie, his face has erupted in hives so bad they look more like lesions. While he never appears in the prologue, it's stated that Woogie was a star athlete with rumors circulating that he was going to model in Europe after high school, so even if he wasn't handsome he likely had a more impressive build than Chris Elliot circa 1999.
  • Eye Scream: "You ever had a whitehead on your eyeball, Mary? Hmm?"
  • Foreshadowing:
    • As Dom walks out of Ted's hotel room, he notices Mary walking into the lobby and ducks out of sight. Why would he do this unless they had some history together?
    • Dom knows about the zipper incident, even though Ted never told him. Dom plays it off as having heard the story secondhand in a Suspiciously Specific Denial ("I was only four towns over").
  • In-Series Nickname: "Woogie" derives from his surname Woganowski.
  • Retired Monster: Implied. After Mary got a restraining order and moved away, Woogie settled down with another woman and started a family. When Ted brought her up, Woogie rolled his eyes at the thought that his romantic rival was still obsessed. Then when Ted finds out Mary's still sexy and single, Woogie decides to seize the opportunity and plays Ted so he can get back to mary once more.

The (Unwanted) Suitors

    Pat Healy 
Played by: Matt Dillon
  • Bad Liar: Norm figured Healy out within seconds of meeting him.
  • Bad People Abuse Animals: He drugged Puffy the dog and killed an insect while bragging about the high he gets from helping God's creatures.
  • Bluff the Eavesdropper: Pat realizes that Mary's neighbor is intercepting his cell phone calls, so he fakes a conversation with a friend about his work with impoverished African children and just generally making him look like the greatest guy on Earth.
  • Bunny-Ears Lawyer: For all his many faults Pat is a hell of a bloodhound. As well as something of a Manipulative Bastard.
  • Gasshole: Mary points out that Healy farts in front of her.
  • The Heavy: He's the most prominent of the antagonists and his stalking is shown in full detail while the other guys function offscreen.
  • Kick the Dog: When Healy hangs out with the disabled guys that Mary volunteers for, she witnesses his nasty competitive side while playing football. He also lets one guy almost injure himself just so he could distract Warren long enough to cheat at a game of Checkers. It makes it easier for Mary to not only blow him off for Ted, but Tucker's "intel" on Healy ensures that she'd never speak to him again.
  • Pragmatic Villainy: Healy might drug Puffy, but he'd draw the line at killing him if only because it would create more problems than it would solve.
  • Sir Swears-a-Lot: Pat Healy is the biggest potty-mouth of the cast. He fires a barrage of f-bombs, cluster and precise, throughout the whole film.
    "We had an agreement. You wouldn't fuck me and I wouldn't fuck you until we got this fuck out of the fucking picture!"
  • Slimeball: By far the least benign of Mary's stalkers. He spies on her in broad daylight, casually uses the word "retard" despite knowing Mary has a mentally impaired brother and his lies about being an architect don't seem to hold up under even the mildest of scrutiny. How he managed to charm her is anyone's guess.
  • Tombstone Teeth: Healy got his teeth capped to pander to Mary's tooth fetish. They're very conspicuous and give him a slight lisp.
  • Vitriolic Best Buds: He forms this relationship with Norm.

    Tucker/Norm Phipps 
Played by: Lee Evans
  • Affably Evil: He might be a liar and a stalker, but for the most part Norm doesn't seem particularly hostile. He forms a friendship with Helay after getting outed and offers Ted a drink when the latter tries beating Healy up. When Mary is pressured into picking one of her stalkers, Norm admits that he lied about Healy being worse than he really was as a sign of forfeit.
  • Big Bad Wannabe: While he's not officially the Big Bad, Norm still manipulated events around Mary for his own gain, only for his plans to fall apart as soon as Woogie resurfaces.
  • Bluff the Impostor: Pat, impersonating an architect, meets Mary's friend Tucker, also an architect, who immediately starts grilling him about his work. Eventually it's revealed that Tucker is also an impostor, and that he had pegged Pat as another fake and was trying to catch him in a lie.
  • Fake Brit: In-universe. He's really an American who adopts a posh British accent.
  • Foreshadowing: Tucker repeatedly "jokes" about sleeping with Mary. It's later revealed that he's a fraud and a stalker too, and pretty boorish as well.
  • Inelegant Blubbering: Healey reduces Norm to this with a punch and a headlock.
  • Mock Millionaire: He pretends to be a wealthy, cultured intellectual when he's really just a pizza delivery guy.
  • Obfuscating Disability: He pretends to have a condition which requires crutches but can walk just fine. He actually did genuinely need crutches when he first met Mary but kept them long after.
  • Vitriolic Best Buds: He forms this relationship with Healy.

    Brett Favre 
Played by: Himself
  • Good Counterpart: To Woogie. Both are athletes who dated Mary in the past. Woogie even takes a liking to Brett even if it means Brett gets to be with Mary in the end.
  • The Reveal: Up until his actual appearance, everyone just calls him Brett like he's not a major sports celebrity.
  • Token Good Teammate: While the stalkers aren't a 'team', Brett is the only one who never resorted to deceit or treachery while trying to woo Mary.

Mary's Family

    Warren 
  • Berserk Button: Touching his ears, though Mary points out that he'll make an exception for people he trusts. In the end when Ted removes one of his headphones to say goodbye, Warren cheerfully says good bye right back.
  • Big Fun: He's high-energy, generally gets on well with Mary's dates and just so happens to be overweight. It causes Ted some grief when he wants a piggyback.
  • Companion Cube: He loves his baseball, if he could only find it.
  • Hidden Depths: Despite his mental handicap, Warren can solve a Rubik's cube.

    Charlie 
Played by: Keith David
  • Funny Afro: He sported one when he married Sheila and it reappears during the Dance Party Ending.
  • Horrible Judge of Character: He favors Woogie over Ted. Somewhat justified as Ted triggering Warren by accident didn't create the best of impressions.
  • Papa Wolf: Charlie's very protective of Warren, which is impressive considering he's only Warren's stepfather. For added laughs, he shows concern for Warren after witnessing him kick Ted's ass.
  • Scary Black Man: Subverted with Mary's stepfather. He invokes this for his own amusement just to fuck with Ted, but he's actually quite friendly when he drops the act.
  • Share the Male Pain: When Ted snags his manhood on his fly, Charlie reflexively covers his own groin. Then when he sees the injury up close, he clenches himself like he's hugging a distressed loved one.

    Sheila 
  • Precision F-Strike: She's very polite considering the amount of cringe comedy that went on in her single appearance, but the sight of Ted's snagged snag made her shout "HOLY SHIT!".
  • Strong Family Resemblance: Sheila looks just like a middle-aged version of Mary.

Other Characters

    Magda 
  • Cool Old Lady: In spite of her age, Magda gets on well with women decades younger than herself, keeps tabs on any shady characters in the area to protect Mary and has an active sex life.
  • Fan Disservice: Old age and perpetual tanning have taken their toll on her breasts.

    Puffy 
  • Because You Were Nice to Me: Puffy allowed Healy to swaddle him without complaint after the latter saved him from being set on fire. Clearly Puffy didn't know that Healy drugged him into a coma and tried to revive him with live wires.
  • Canine Companion: Magda's border terrier.
  • Evil-Detecting Dog: Magda says that Puffy only barks at bad guys, though Mary suspects he doesn't like men in general.
  • Pint-Sized Powerhouse: Ingesting speed gave Puffy enough strength to dominate Ted.

    The Hitchhiker 
  • Ax-Crazy: He carries a camperbag containing a hacked up body and was visibly losing his marbles when Ted criticised his businessplan.
  • Motor Mouth: He doesn't shut up about his pitch to sell fitness videos, which segues into some nonsensical ramblings that don't stop even when Ted exits the car.
  • Red Herring: He's about the same age as Ted and Mary and shows signs of being unstable, with Dom stating that he was planning to cut Ted's throat. He also disappears halfway through the movie. With information like that, it seemed like he was going to be revealed at the film's climax as Woogie, but Woogie turns out to be someone else.

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