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  • 88 49
    Submitted by GetOffMyLawn on Aug 26, 12 at 6:01pm

    I don't understand why this is awkward but then again I have a vanishingly small sense of shame.

  • 83 66
    Submitted by cfreymarc on Aug 26, 12 at 3:15pm

    Better she knew your mom.

  • 66 46
    Submitted by _assh00le_ on Aug 26, 12 at 10:44pm

    Oh god your heart drops lol

  • 67 53
    Submitted by pnr on Aug 26, 12 at 2:44pm

    Wait wouldn't she be a MIF(ed) and not a milf

    • 60 65
      Submitted by wubbazugg on Aug 26, 12 at 3:12pm

      Hooking up with a MILF does not change MILF status.\nAnd, you never know how old they are in a reference like this. She could be as old as his sister.

      • 44 60
        Submitted by budman999 on Aug 26, 12 at 9:42pm

        Think you completely missed pnr's joke here

      • 49 45
        Submitted by ieatfood717 on Aug 27, 12 at 4:29pm

        For the record: she's 40, I'm 24.

  • 55 46
    Submitted by ieatfood717 on Aug 27, 12 at 4:28pm

    Haaaaaahahahaha. Oh my goodness. This is my text, my friend submitted it. I feel so legitimized.

  • 56 58
    Submitted by bigjwin on Aug 26, 12 at 2:54pm

    That's called having balls!