“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 Twitter Legend Simon Holland

EDITORS’ NOTE: We’re In the Powder Room today with “Ask a Man,” our 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 humorist, Twitter comedian, and meme-maker extraordinaire Simon Holland! Simon has been featured in MANY tweet roundups, including those put together by The Huffington Post, BuzzFeed, and Scary Mommy. His tweets can also be found in The Big Book of Parenting Tweets and The Bigger Book of Parenting Tweets, both available from Science of Parenthood Press.

Ask a Man In the Powder Room featuring Twitter legend Simon Holland

Jocelyn Pihlaga (O Mighty Crisis): When is the first time you remember being funny?

Simon: When I was a kid, my grandmother would make my cousins and I put on little performances during the holidays. We would have to sing, or do a skit, or recite poetry, or something else that we all hated at the time but is now the source of some amazing memories. When I was maybe nine years old, I was doing a skit with my sister when I saw my aunts and uncles laugh real laughter instead of the fake stuff grownups usually respond with to kids. I remember thinking how fun it was, and maybe I’ve been trying to make people laugh ever since.


Sarah Halsall del Rio (est. 1975)We all know you stood at the crossroads and made a deal with the devil. What were the terms?

Simon: Wouldn’t it be awesome if I could look at you like Clint Eastwood right now and say: “I didn’t make a deal with the devil; the devil made a deal with me.” That would seriously be badass, but also neither true nor accurate.

Sarah: Do you have any Twitter crushes? If so, are you willing to share their identities?

Simon: *holds up a sign that says “TOO MANY TO NAME” while typing “I am not sure what that is and of course not”*

Melanie Loveday Madamba (The Not So Super Mom)You are the funniest dad on Twitter. If someone were to have a pathetically unreciprocated Twitter crush on YOU, what would you wish her to be like? Asking for a friend.

Simon: I am actually the 32nd funniest dad on Twitter, but I’m super flattered to have fooled you for this long. I love people on Twitter who are unique, funny, and a bit self-deprecating. I also feel like anyone misguided enough to have a Twitter crush on me should also be sending me cupcakes with wrappers made out of folded-up twenty dollar bills.

Jocelyn Jane Cox (The Home Tome)What do you generally bring to a potluck?

Simon: If I’m being honest I always volunteer to bring paper plates and plastic cups, but I also make a white chicken chili I’ve named the Ragin’ Caucasian that is en fuego.

Jocelyn: As far as mowing your lawn goes, are you an advocate for horizontal stripes, diagonal stripes, or concentric circles?


Jocelyn: Do you, or have you ever, owned your own bowling shoes?

Simon: I do not, and have not. When I see a guy walk into the bowling alley with his own bowling shoes, I do get a bit jealous, but then I remember it is actually better to walk in with a date instead. That was a sick burn on guys with bowling shoes, but remember this is all in good fun.

Stacey Gill (One Funny Motha)Does your spouse think you’re funny?

Simon: She does, but she keeps me in check quite a bit. Our senses of humor are a bit different, and she helps reel me in when I get too weird.

Ask a Man featuring Simon Holland In the Powder Room

Stacey: Has anything you’ve ever written caused a conflict with your spouse/family?

Simon: Once my mother checked to make sure I was doing ok and not really drinking hard booze in the morning and dealing with a drinking problem because of some tweets I wrote.

Stacey: What were you like in high school? What clique did you fall into?

Simon: I had a really good high school experience which is probably why I am only the 32nd funniest dad on twitter, you have to have some real pain and angst to turn it into true humor. I was athletic and smart enough to be lazy but I really found a home on stage. I actually went to college on a theater scholarship for a year so I guess I turned into a drama nerd but those chorus girls were worth it.

Darcy Perdu (So Then Stories)

When are you self-publishing “The Best of Simon Holland’s Memes, Tweets & Toots” for all to read, laugh, and emulate? I’ll buy the first copy!

Simon: Does this sentence constitute a legally binging contract? Can anyone give me a ruling on that because if yes I am making one book and pricing it very very high.


Lance Burson (My Blog Can Beat Up Your Blog)When you tell your kids what to do, do you preface it with Simon Says and does that work? How about with your wife?

Simon: Bahahahahahahahahahahahaha deep breath hahahahahahahaha. No, that doesn’t work not even once, I hate that stupid game.

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Simon Holland (@simoncholland) is just a guy that likes to write jokes, then put them on the Internet so that they can get stolen. He is also writing this bio in the third person because it sounds more professional than writing it in the first person. If Simon’s life was made into a movie, the actor playing him would probably just be whomever is best at walking around the house turning out lights. Seriously, if his kids knew there was a light in the oven, they would leave that one on too. Simon’s kids will eventually get older and he will have nothing left to be funny about so please, just give him this. He needs it, if even for just a little while.

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