“Ask a Man,” a monthly feature in which a MAN (gasp!) joins us in the stalls so we can ask him a bunch of crazy questions.

Ask a Man: Humorist and Beard Mentor Jeff Terry

EDITORS’ NOTE: We’re In the Powder Room today with “Ask a Man,” our new monthly feature in which a MAN (gasp!) joins us in the stalls so we can ask him a bunch of crazy questions!

This month’s “Ask a Man” guest is writer, humorist, and marketing diva Jeff Terry. Jeff favors Pumpkin Spice Lattes and has a sleeveless sugar skull shirt that makes him look like a douche. He blogs at Jeff & Jill Went Up the Hill.

"Ask a Man" featuring Jeff Terry In the Powder Room

Linda Roy (Linda Roy Writes)Which three comedians—dead or alive—would you knock back some tasty craft brews with? What would you most like to discuss with them, and which brew do you think each would order?

Jeff: Steven Wright. He’d drink something calming—like a heavy stout or something. I’d talk to him about what it’s like to have fans, to have people want to drink with you, and to have people actually laugh at the things you say.

Molly Shannon. She’d order an IPA with blood orange garnish—she’d call it “The Superstar”—and she wouldn’t drink it, she’d just toss it in my face. And I would still not be worthy. I’d to talk to her about mentoring my daughter, because the world needs more Molly Shannons.

Will Ferrell. He’d drink Old Milwaukee—but I wouldn’t. I’d ask him what it was like to work with Molly Shannon. I’d also ask if he has Zach Galifianakis’ phone number.

Sarah del Rio (est. 1975)My cat is licking her foot right now. What do *you* do in your spare time?

Jeff: My spare time involves very little cat-licking after graduating from the treatment facility. Now in my spare time, I collect spare tires. I have one going around my waist right now that screams “Badyear.”


Ali Solomon (Wiggle Room)Who would play you in the TV movie based on your life? What would that movie be titled? And would there be any work as an extra for a 30-something mom looking to get her SAG card?

Jeff: Tom Sizemore would play me, because he is just that desperate. The movie would be titled Fish Sticks and Dick Pics, to “generate buzz.” And yeah, there’s work for a 30-something mom with an appetite for fish sticks. Just sign the waiver.


Jocelyn Jane Cox (The Home Tome)What is the best advice you can give to people aspiring to be Jeff Terry?

Jeff: My advice would be to push past all the doubt, fear, anxiety, loneliness, despair, degradation, and self-loathing until you arrive at numb confusion. Numb confusion is the best you can hope for. Good luck.


Stephanie Marsh (We Don’t Chew Glass)Why do you live in a place where there are people?

Jeff: Because people are crawling all over this cosmic speck. And I would die if I had to do things like build a fire or go outside. But I’ve compensated for my need to live near people by wrapping myself in a cocoon of discomfort and awkwardness that repels almost everybody.


Jeff Terry models "that purple blazer from Marshall's"Tara Wood (Love Morning Wood): What is your biggest regret and/or proudest moment in your life? (I’m guessing both answers have something to do with that purple blazer from Marshall’s.)

Jeff: My proudest moment is right now. No one’s ever asked for my thoughts before. *wipes away big manly tear*

My biggest regret is not buying the purple corduroy pants that went with the blazer. *wipes away little manly tear*


Aussa Lorens (Hacker. Ninja. Hooker. Spy)What’s the weirdest thing you’ve ever put in your mouth?

Jeff: Bird poop. To be clear, I didn’t put the bird poop in my mouth. An angry momma bird did that. She pooped right in there.

Rodney Lacroix (Rodney Lacroix, Writer)I’ve been thinking about growing a sweet, sweet beard like yours. Unfortunately, when my facial hair grows in, it comes out in giant patches so most people just assume I have facial mange. I guess my question is: can I have your beard?

Jeff: Yes. For three easy payments of only $89.97, I’ll send you my secret Bro Gro Formula® and twelve instructional cassettes. And since Bro Gro respects customer privacy, we’ll appear on your credit card statement as PORN AND NEEDLES so no one will know that you are trying to grow a beard.


Don Re (Don of All Trades)Have you ever successfully found a clitoris? If yes, did you know what to do with it? Unrelated, how good are you at drawing maps and writing instructions?

RELATED: “Ask a Man: Policeman, Father, Humorist Don Re”

Jeff: Once, armed with a machete and a Maglite, I went in search of one. I lost five brave men on that expedition. And I’m still not sure I found it. There was something. But . . . it was so dark. And I was rushed! The screams, though. I still hear them! I can still hear them, man!

This original piece was written exclusively for In the Powder Rooma division of Hold My Purse Productions, LLC. Featured image © RetroClipArt via depositphotos.com.

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Jeff tries to hide from his problems by focusing intently on them at Jeffandjillwentupthehill.com. He lives close enough to Chicago to claim that he lives in Chicago with his wife Jill and their three kids. He writes to make himself laugh. His goal is to provide the finest nothing on the Internet. He hopes you visit and enjoy a braincation. Whatever that is. Connect with him on Twitter @jeffingoff and on Facebook.

Keep the conversation going...



  1. says

    You had me at sleeveless sugar skull shirt that makes him look like a douche….LOL!

    I want to have a man crush on Jeff Terry, but he has a beard and I find people who purposely have beards to be churlish, very douchey, pedantic and off putting. I hate them, as much as I would a person who would use the word pedantic or churlish in a sentence.

    Shave your beard, Jeff Terry, so that I may come visit you in Chicago and spend quality time doing stuff.