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May 15

In another exciting episode of ASK EBENGREGORY, Jeremy from South Beach, Miami wants to know if it’s cool to date his best friends mother.

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11 Responses to “ASK EBENGREGORY: Dating My Homeboy’s Mother”

  1. Sasucule Says:

    That’s one way to lose a homeboy. Ooooooh Nooooo!!

  2. Pot3000 Says:

    Man dude need to fuck the dog shit outta that rich bitch

  3. GirlWonder Says:

    THANK YOU SASUCULE!!!
    And if u gotta ask, then hell naw…

    …n***as….

  4. Herstory True Says:

    She wants to be his suga mama… I say go for it, but keep it a secret …. homeboy gonna kick his azz

  5. Sasucule Says:

    Yeah Herstory True your right. If she’s rich divorced and looks like Halley Barry then forget the Homeboy. Fuck that bitch. Don’t even keep it a secret. Unless your scared of the nigga. Sorry GirlWonder I had to keep it real.

  6. AIR MAX Says:

    I wouldn’t put that shit on blast… but I’d bang the shit our of her… till the wall of her vagina caved in. I’m keeping it real.

    Sh… if you got to ask then it would be wise to keep it to yourself.

  7. Swagger2000 Says:

    Yeah all ya’ll think that shit is cool… Your best friend is gonna be fucking ya’lls daughter’s hell maybe even your son’s in the future. Karma is a mofo and if you would even thinking about smashing your Friend’s” mom then you a foul nigga anyway in my opinion.

    You lost points with that Eben. That is disrespect on all levels with your friend’s mom. But to each his own

  8. KAEDEE08 Says:

    I wouldn’t ,i wouldn’t even f**k his girl BUT I would f**k my girl’s mom .lol It just seem right to me …did it a few times . srry :(

  9. freeza924 Says:

    if dude slimy enough to plot on moms than he never was a friend

  10. brightseatbully Says:

    ^^^^ that’s as real as it gets.

  11. Sasucule Says:

    Yeah I was just joking, this isn’t cool at all. You wouldn’t want that to happen to your Momma. Some scum bag of a homie using her for sex.



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