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1,855 Funny Votes
390 Die Votes
50,036 Views
Published March 21, 2011

Screen shot 2011-03-21 at 2.02.10 PM.pngNeed dating advice from Jimmy? Send your letter to:

Girl Talk with Jimmy
P.S. 251
Ms. Kellemen's 3rd Grade class
NY, NY




Dear Jimmy,
There's a girl in my office that I've fallen for. She works in HR, which makes things that much more awkward. If I make things uncomfortable for her, I could easily get fired. But I like her so much. How do I subtly make it known I have feelings for her?
-Crushin' in my Cubicle


Dear Crushin,
This is a tough one since Valentine's Day has already passed and you can no longer tell 30 people at once that you love them. Have you tried punching her in front of all your friends?
Smell ya,
Jimmy

****

Dear Jimmy,
My girlfriend is pressuring me to get married. But mentally I'm not ready. It has nothing to do with her, honestly. But I don't want her to feel let down with each passing day. Any suggestions?
-Cold Feet in California


Dear Cold,
You should do that. My parents are married and are very happy. My Mom often screams "THANKS FOR NOTHING" to my dad. She's so happy and my dad didn't have to do anything. Marriage sounds great.
Happy!
Jimmy

****

Dear Jimmy,
I've been with my girlfriend for over a year and I've yet to bring her to orgasm. Any tips?
-Impotent in Iowa


Dear Important,
Bears maybe? That's probably the best orgasm there is. You should bring her that.
Bears rule!
Jimmy

****

Dear Jimmy,
I wrote to you a few weeks ago about pleasuring my girlfriend. You wrote something about bears. My guess is that it's because you're a child and didn't know the difference between an orgasm and an organism. No big deal. I knew what I was getting into when I sought your advice. But seriously, I'd love any tips you could give me on making my girlfriend feel good in bed.
-Still Impotent in Iowa


Dear Still Impotent,
As a licensed sex therapist, I think I know the difference between orgasm and organism. Like I said, bears.
-Jimmy

****

Dear Jimmy,
Impotent again. I'm very sorry I questioned you. But when I introduced bears into the bedroom, my girlfriend scoffed. Then she was eaten by the bears. What now?
-On the Run and Impotent in Iowa


Dear On the Run,
Hahaha. Yeah, bears sure are funny. One time at the zoo, I saw a bear. It was the best day of my life.
Bears still rule!
Jimmy

****

Dear Jimmy,
My deceased girlfriend's parents has had me arrested for the murder of their daughter. Do you know any good lawyers?
-Incarcerated in Iowa


Dear Incarcerated,
Sorry it took me so long to respond. I've been at swim class.
-Jimmy

****

Dear Jimmy,
You've been in swim class for the last 7 months??? I'm rotting in here, you little shit.
-Seething in Cell Block 9


Dear Seething,
I'm done with 3rd grade so this project is over. Thanks for being my pen pal!
Love,
Jimmy
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