Women Interested in Unappealing Men

Table Of Contents

Explanation of Conservative Trope

In real life, people are usually not interested in unappealing men or women. But on screen, they will sometimes depict unappealing men having success with women but rarely the other way around. The idea is you are rooting for the male "underdog" to get the woman he likes.

Conservative Trope Examples

  • Bad Santa 2 (2016)
    An attractive staff member at a lavish party walks up to a disheveled Willie (Billy Bob Thornton) in his Santa costume, hands him a glass of whisky they both quickly chug and then takes him to a private room where she pleasured him with her hand.
  • Diane (Christina Hendricks) drives up to Willie (Billy Bob Thornton) and tells him that even though she's married she isn't happy and "sometimes I need to be bad." They then go have sex next to a dumpster in an alley while she repeatedly asks him to say degrading and dehumanizing things to her.
  • We're the Millers (2013) | Attractive Women Interested in "Losers"
    Casey Mathis (Emma Roberts) goes out with a boy who talks using stereotypical dumb young people slang and has a misspelled "No Ragrets" tattoo on his collar bone that when asked says he has no regrets about getting it.
  • The Way Way Back (2013)
    Pam (Toni Collette) is depicted as very dependent on her boyfriend Trent (Steve Carell) who also treats her and her son poorly throughout the entire movie. She also still stays with him despite finding out he cheated on her. Pam's only act to stand up for herself is she moved to sit next to her son rather than Trent in their station wagon in the closing scene.
  • Mary (Sandra Bullock) is obsessed with Steve (Bradley Cooper) even though he dresses in disguise to confuse her, drives away from her and her friends who are stranded on the side of the road after being hit by a tornado, and watches her run straight into a sinkhole without saying a peep.
  • My Best Friends Girl (2008) | Women Attracted to "Bad Boys"
    A woman at the bar initially calls Tank (Dane Cook) "an a*shole," but quickly changes her tune and decides to go home with him after he tells her to "walk away" if she really thinks that he is.
  • Knocked Up (2007)
    Recently promoted reporter Alison Scott (Katherine Heigl) has a drunken one-night stand with slacker loser Ben Stone (Seth Rogan). She gets pregnant and decides to keep the baby.
  • Disturbia (2007)
    Kale (Shia LaBeouf) plays loud music to disrupt the party his neighbor Ashley -- who he's only briefly met -- is having because he likes her and is jealous. She comes over to stop it and confront him. He confesses he’s been watching her and clarifying that he's "only looking at you". She says that’s either the creepiest or sweetest thing she’s ever heard and then they make out in his bed.
    Staff Aside
    I guess it was the sweetest then?
  • Danielle (Jordan Ladd) complains to Raddimus (Luis Guzman) that he treats her "like a piece of meat" and he responds "not just any meat, baby. A prime rib."
  • The Girl Next Door (2004) | Women Attracted to "Bad Boys"
    Kelly (Timothy Olyphant) is a prototypical bad boy talking with three senior high school women 20 years younger than him. They are flattered and flirty with him despite his creepiness trying to recruit them for adult films.
  • Fiona breaks up with her boyfriend Scott "Scotty" Thomas for "bad boy" singer Matt Damon covered with tattoos and piercings. Scott finds out later that night she's been having an affair when Matt Damon kisses Fiona on stage and wishes her a happy *anniversary* before his band performs a song about it at their graduation party called "Scotty Doesn't Know".
    Staff Aside
    This is a great and hilarious cameo by Matt Damon. It's really funny. But what's great fun on screen sometimes has consequences off it -- where some men may think they'll do better with the ladies by acting like a "bad boy."
  • Bad Santa (2003)
    Sue flirts with a dirty, drunk, and exhausted looking Willie (Billy Bob Thornton) still in his Santa costume from behind the bar. He flippantly tells her he's just an "eating, drinking, sh*tting, f*cking Santa Claus" and she inexplicably responds to his rant by saying "prove it." Moments later they are having sex in his car while she moans "f*ck me Santa" over and over.
  • The New Guy (2002) | Women Attracted to "Bad Boys"
    Dizzy is depicted as a nerd who gets bullied in high school until prison inmate Luther consults with him on changing his image. He changes his name to Gil and gets dropped off at a different high school by a prison van, beats up a school bully and acts like a stereotypical over the top bad boy. And it all works and he becomes popular and the girls in school are attracted to him including one in an impressed voice asking, "you were in jail?" and then inviting him to a party.
  • Bridget Joness Diary (2001) | Women Attracted to Men Who Treat Them Badly
    Daniel (Hugh Grant) patronizingly tells Bridget (Renée Zellweger) to "just slow down. It started on Tuesday and now it's Thursday. It's not exactly a long-term relationship, is it?" after she expresses concern about what the rest of the office will think of their relationship.
  • American Pie (1999) | Women Attracted to "Bad Boys"
    Paul Finch (Eddie Kaye Thomas) is portrayed as a nice guy who is respectful and intellectual which is inferred to be why he is single as girls are not interested in him. He pays a student, Jessica, to spread rumors that make him appear to be a "bad boy" such as that he beat up Stifler. And the result is that women express interest and start asking about him believing the fake rumors are true.
  • Harry and Lloyd are depicted as unattractive losers who are extremely dumb (hence the title). Yet when stranded on a desert highway, a Hawaiian Tropic tour bus stops and several women in bikinis open their windows to greet them. A few women come out and say they need "two oil boys who can grease us up before each competition," but because they are so dumb they point them towards town rather than get on board.
    Staff Aside
    This is obviously played for laughs, but in what world would two guys like Harry and Lloyd be asked to be oil boys for a traveling bikini team?!
  • Say Anything (1989)
    Lloyd Dobler is depicted as an underachiever but ends up dating the valedictorian Diane Court despite not having much of anything in common.
  • Ferris Bueller's Day Off (1986) | Women Attracted to "Bad Boys"
    Jeanie Bueller (Jennifer Grey) meets a bad boy loser in trouble for drugs played by Charlie Sheen while waiting in the police station for her mother to show up. At first, she is repulsed by him, but not long after they are making out.
  • Maverick (Tom Cruise) makes a bet with his best friend Goose (Anthony Edwards) about whether he can have "carnal knowledge" of a woman at a bar. He and Goose do their routine and Maverick sings "You've Lost That Love & Feeling" to Charlie (Kelly McGillis) as his fellow pilots join in. She declines his invitation to join him and goes to her date's table instead. Undeterred, Maverick follows her into the women's restroom to try again to get her to go out with him. He "crashes and burns" but eventually his over pursuing works and they start a relationship.
    Staff Aside
    Imagine how many times women had to put up with overly aggressive men who won't take no for an answer after having this iconic scene eventually pay off for Maverick in Top Gun. Or guys making bets about having sex -- oops I mean *carnal knowledge" -- with a woman you meet at a bar. Picture this same scene replacing 'carnal knowledge' with 'sex' and it becomes awkward and weird.