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MILF Monday: Maggie Gyllenhaal

 
Where You’ve Seen Her: Maggie Gyllenhaal may not be traditionally hot, but damn if you wouldn’t do dirty things to her in the picture above.  She did a lot of this stuff in Secretary with James Spader, who was her boss in the film.  Oh, the things I would do to have a secretary like that too.
 
MILF Status: Maggie has a daughter named Ramona with actor Peter Skaarsgard.  Now Ramona can tell her teacher about the movie Secretary when she explains what her mom does for a living.
 

         
         
 

34 Responses to "MILF Monday: Maggie Gyllenhaal"

  1. Dwight K. Schrute says:

    Those were CGI, idiot! Maggie is in the same catagory as Sarah Jessica Parker, a fugly bitch with no redemable qualities, stupid!

  2. KingGreat says:

    I have to agree with everyone else. She is far beyond plain, and borders on repulsive. Not for nothing HT, but how did you actually manage to run out of girls on the internet? I’m aware there’s a finite number of women, but let’s not carried away with the MILF spotlight. By the way, DonkeyXote’s comments bore me. How’s about you guys make an entry apologizing for such things as DonkeyXote’s ennui, ugly MILFs, frequently difficult-to-read captcha, and other stupid shit. Thanks.

  3. Breefbisk says:

    I for one agree with you on this pick, HT. Not traditional but somehow extremely sexy.

  4. Fist of Rage says:

    She’s hot if you have an butterface fetish. There’s a lot of smoke and mirrors going on there. MILF should at least be an 8 without makeup. She is a 2 with makeup. She looks like basset hound for cryin out loud.

  5. DonkeyXote says:

    That a light-weight belt on her?

    LeT’s GeT ReAdY To RuUuUuuUUUuuMmmBlE!!!!!!

  6. Mwawhaw says:

    She might be one of the ugliest chicks in Hollywood right now, BUT she makes up for it with good acting AND she’s probably still hotter than most of you guys girlfriends… cause you all got none !!!

    So how ’bout that ?

  7. Stick says:

    Yes, she was awesome in Secretary. It was a great movie. James Spader and her really master the whole subtly thing.

  8. WTF says:

    Not only is she not attractive, she’s a fucking idiot too. She’s as dumb as a bag of hammers.

  9. Hate you! says:

    I love assholes like you who sit at their keyboard and they know what the other posters have or don’t have, asshole, but I repeat myself.

  10. justin bieber says:

    I love MILF Mondays and Maggie Gyllennnnnhaal,
    Your a straight up homo if you think other wise!

  11. Wow you all suck says:

    She is so fine. I think you guys are all cracked.

  12. Giggity says:

    Jake is cuter

  13. Dwight K. Schrute says:

    Congratulations HT, you will now be put on probation, another fugly ass chick that you put on and your man-cards will be voided, idiots!

  14. DonkeyXote's Mom says:

    NO, remember, she got that for being the millionth person to successfully ass-rape you. Now go and finish sucking your grandpa dry you douche!

  15. she is seriously fugly. says:

    i’d rather fuck jake.

  16. MILF says:

    I love MILF Mondays as well! Check out more hot milfs http://www.milfseeker.com

  17. she is super sexy!! says:

    If you ever see the movie strip search you will see that Maggie has the tits of a goddess.

  18. FunkyMunkey says:

    Redeemable qualities? Is she a fucking voucher or something?

  19. Anonymussy says:

    Hey no cuts you asshole, I was in line first to get my rimmed worked! unless you wanna fuck it then I might reconsider my place int he queue.

  20. Baba Flow-hai says:

    This bitch is so fucking ugly. Help.

  21. B.A. Barracus says:

    I agree, one of the best parts of Dark Knight was when Maggie Gyllenhaal got blown up. She sucks.

  22. sheisugly says:

    She is ugly. This was a terrible pick. I’m glad she died in The Dark Knight.

  23. Ben Affleck says:

    She is second only to Shelly DuVall as the ugliest person in hollywood. And yes, I did consider people like Whoopie Goldberg and that old woman in every adam sandler movie.

    BARF!

  24. Gourry says:

    why is her face melting off? she’s gross

  25. Briane Pagel says:

    She was number one on this list:

    http://www.troublewithroy.com/2008/12/semidaily-tboe-list-best-actresses.html

    So I totally agree with the MILF Monday post.

  26. Boknaai says:

    Alektra Blue’s Training Partner , too much to read. A simple “first’ or even “first, you motherfuckers’ is all that is expected of a first responder. Please get with the program and save the lengthy posts for much later down when most people don’t give a toss.

  27. Alektra Blue's Training Partner says:

    Maggie Gyllenhaal may not be traditionally hot…” Ht, you might want to rephrase that to, “Maggie Gyllenhaal is fucking ugly, and is proud to say that the sexual apex of her lifetime was giving an HJ to the assistant drum major of her high school marching band behind the snack bar at a football game.”

  28. Olala says:

    FAIL!!!!!!!!!!! saying first is lame, you get with the program you stupid ass motherfucka!!!!!!!!!!!!!!!!!!!!!!!!

  29. alalO says:

    Isn’t that mothafucka, you stupid bunghole licking fudge packer?

  30. islandmanagers says:

    M.G. is a classic case of “not hot, but TOTALLY sexy”! I’ve been a huge fan her entire career. Before her, the n.h.b.T.s. babes were Janene Garafalo and Julia Louis-Dreyfus. They’ve just GOT IT. Yum, Yum!!

  31. Dante says:

    Yea she’s not that attractive

  32. JAke Gyllenhaal says:

    Wow put a cowboy hat on him and we’ll go for a ride some time..

  33. pratik says:

    Kermit goatse > this.


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