Ask The Dipshit

Jonathan Ass
2 min readMay 18, 2019

Part 1 of an ongoing series wherein our beloved readers ask a man known only as “The Dipshit” for life advice

funny picture I found. Unrelated to the advice found below

Dear Dipshit,

I’m going on my fifth date this weekend with this great girl named Andrea. She’s smart, she’s funny, she’s absolutely beautiful, and most surprisingly of all, she seems like she’s genuinely interested in me. She is an avid reader, she volunteers at a soup kitchen every Sunday, and our dogs even get along! It was snowing when I dropped her off after our fourth date, and we shared a passionate kiss before she went into her apartment. Being around her just feels comfortable. I really, really like her. I know it’s early, and I’ve been burned before, but I think she might be the one. However, there’s one small problem.

When I was 19, my dick and balls were separated from my body in an accident while I was working in a factory. I don’t want to go into too much detail, but there’s nothing down there anymore that has any sexual use whatsoever. I guess my question is, how long should I wait in our relationship before revealing my dick and balls were blown off in a horrific smelting accident? When should I tell the potential love of my life that there’s an amalgam of mangled flesh where my genitalia should be? Your counsel is much appreciated!

Sincerely,

Dickless in Denver

Dear Dickless in Denver,

Oh man that sucks. Thank God that never happened to me. Jesus christ, what a little freak you must be, just walking around all smooth down there like some kind of alien. My first piece of advice to you would be to kill yourself. How could anyone ever love you?

However, if you are too much of a coward for suicide, you could just be honest with her. No need to rush anything. The time will come when she wants to escalate the physical relationship and you’re just going to have to sit her down and say to her, “Rachel, listen. I care about you deeply but there’s something I need to tell you about before this relationship progresses any further. This is really hard for me and I’m ashamed and embarrassed but I care about you too much to not tell you the truth. Due to an unfortunate accident when I was younger, I’m a dickless little freak. A carnival loiterer level-weirdo. I can never love and no one can ever love me. (Barking like a dog). Get away from me! Can’t you see we don’t want you here anymore?” If she doesn’t run screaming out of the Sbarro’s, know that you’ve found the one, and you can get married immediately. You’re welcome.

Thanks for writing.

Sincerely yours,

The Dipshit

--

--