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  • Submitted by ShitThrwnMonky on Jul 8, 10 at 4:24pm

    Ask if she also cleans pipes

  • Submitted by Soviet_Russiaa on Jul 8, 10 at 3:14pm

    Stick it in her

  • Submitted by rider8511 on Jul 8, 10 at 3:39pm

    Make her call you papi while you're at it.

  • 91 59
    Submitted by buzzcutt on Jul 8, 10 at 5:32pm

    awkward is being handed a golden opportunity and being too big of a dipshit to seal the deal...

  • 98 73
    Submitted by fleischer911 on Jul 8, 10 at 5:02pm

    Pump your fist and screw her at the same time. Yea jersey!

  • 88 55
    Submitted by squibkick on Jul 8, 10 at 8:14pm

    Tell her you got her a new broom to use and it's in the pants closet.

  • 91 67
    Submitted by FetusPuncher on Jul 8, 10 at 3:24pm

    Make an amateur porn movie

  • 85 69
    Submitted by tswift4eva on Jul 8, 10 at 7:35pm

    this begs the question: why did you have a hardcore boner in the KITCHEN?

  • 80 75
    Submitted by Anonymous on Jul 8, 10 at 10:15pm

    We need more lemon pledge...

  • 70 61
    Submitted by awesomesaucechk on Jul 8, 10 at 7:43pm

    I wish I was the cleaning lady

  • 73 70
    Submitted by thenewguy10 on Jul 8, 10 at 5:19pm

    I don't know...of she's hot, just go with it man.

  • 64 52
    Submitted by rpw641 on Jul 8, 10 at 5:09pm

    Happened to me before haha

  • 71 68
    Submitted by MP9090 on Jul 8, 10 at 5:24pm

    Other awkward cleaning lady moments: peeing after she cleaned the bathroom.

  • 71 71
    Submitted by SilverKnight on Jul 8, 10 at 3:24pm

    Gauge her interest in it, then strike :)

  • 66 64
    Submitted by niceman on Jul 8, 10 at 6:25pm

    Just fucking fuck her, you moron

  • 60 60
    Submitted by ThatsMyAss on Jul 9, 10 at 7:09am

    Hey emily, some people actually had to work to be rich. Not everyone has it handed to them by a rich family member. And no matter if he is a spoiled rich kid or someone successful because they have a good career, you should get off your high horse and stop looking down on people because deep down you wish you could live like them.

  • 57 56
    Submitted by oregon_donor on Jul 8, 10 at 9:59pm

    couldve been one of those naked cleaning ladies from craigslist

  • 54 53
    Submitted by AwkwardBalloon on Jul 8, 10 at 10:10pm

    awkwatd balloon

  • Submitted by Goh7 on Jul 8, 10 at 7:14pm

    why papi you asshole ?? just because she is a cleaning lady she has to be from latin america?? you racist prick

  • 61 68
    Submitted by austinonymouss on Jul 9, 10 at 2:34am

    Must be the mornin' lol happens all the time

  • 60 69
    Submitted by Spark228 on Jul 9, 10 at 2:33am

    No no, misure superman no es here

  • 66 82
    Submitted by Michguy on Jul 8, 10 at 4:20pm

    Loser for not knowing what to do.

  • 57 65
    Submitted by HR_paperstacks on Jul 8, 10 at 11:30pm

    U have a cleaning lady so that means u got some money, so nothing should be awkward for u

  • 55 68
    Submitted by kmomokbs on Jul 9, 10 at 2:40am

    fuck her brains out cuz your the boss

  • 48 55
    Submitted by snarf on Jul 9, 10 at 3:50pm

    ThatsMyAss, u r a major cocksuck!\nWho cares if some1 is rich u dick!

  • 56 72
    Submitted by chastine on Jul 8, 10 at 5:21pm

    That is so hot I would have fucked her haha

  • 55 73
    Submitted by squibkick on Jul 8, 10 at 8:18pm

    Awkward would be the cleaning lady is really your mother and your giving her the one gun salute because your fantasizing about it.

  • 51 65
    Submitted by Goh7 on Jul 8, 10 at 7:19pm

    f-u rider8511

  • 30 33
    Submitted by ShadowLion on Jun 15, 11 at 10:30am

    Arnold's at it again

  • 44 61
    Submitted by Hobbz on Jul 8, 10 at 11:53pm

    Yea Jersey!!!!!!!!!

  • 63 99
    Submitted by gixxer209 on Jul 8, 10 at 4:34pm

    Ask her to remove the lint from your balls with her tongue

  • 47 69
    Submitted by beautifulfeet on Jul 9, 10 at 12:47am

    That's hott!

  • 57 94
    Submitted by BeautyMonster on Jul 8, 10 at 4:19pm

    Same area code as me. Ah, the joys of Jersey.

  • 47 75
    Submitted by mcq53 on Jul 9, 10 at 5:12pm

    Goh7 why so sensitive? It was a joke grow a pair and laugh bitch

  • 41 64
    Submitted by leadbelly on Jul 8, 10 at 11:57pm

    Old mother Hubberd went to the cupboard,

  • Submitted by emilyjune on Jul 9, 10 at 12:38am

    Who the hell has a cleaning lady? Are you that rich and lazy that you can't clean your own damn house? I frown upon people like you who will never understand what work is..

  • 42 82
    Submitted by oregon_donor on Jul 8, 10 at 5:12pm

    its...an optical illusion...aw who am i kidding