Funny AF Woman # 18

Sheila Moeschen

I first noticed Sheila in the comments of

Michael Estrin

’s Substack. Her replies were always funny, sharp and pithy. Then she teamed up with

Beth Lisogorsky

,

Ingrid Haring-Mendes

and

Lior Zaltzman

to review the hilarious TV show, Nobody Wants This. Turns out she knows how to inject charm and wit into a review too.

Sheila recently upcycled her stack and it’s now called Humor Saves! (Wish I thought of that title.) She’s multitalented. I will shut up and let her speak for herself now…

1. What were your life events that lead you to realize, “Hey, I’m pretty funny.”

   Humor in some form was a constant growing up. My dad enjoyed lots of classic comedy–Sid Caesar, Mel Brooks, Danny Kaye. So it was sort of baked into my homelife. I found my way into a bigger comedy world pretty early on. For me it was a short jump from The Muppets and sitcoms to things like Weird Al and The Dr. Demento Radio Show and then SNL and stand-up comics like Paula Poundstone, Steven Wright (I am a Gen X-er, so this was during the stand-up boom of the 80s). Funny was sort of our family language, so I knew I could hold my own with my older brother. I was also that typical kid that used humor as a defense mechanism early on in social settings, but that’s what I knew it was.

   I didn’t think about being “funny on purpose” until I was in high school. I was a sophomore cast in a play opposite a guy who was a senior and who I had a gigantic crush on (of course). I was always so nervous around him that I was pretty unfiltered and goofy. We would spend a lot of our time offstage joshing and riffing. One day I said something that cracked him up and he stopped and goes: “You know, most girls think they’re funny, but you…you’re REALLY funny.” It was better than a promposal. As dopey as it sounds, it felt like being anointed. It left a mark–clearly.

2. If you’re in a partnership, is he or she funny? Was/Is humor a requirement?

   I am married, and I always describe my partner as being a great “straight man” for my daily comedy shenanigans. He can definitely hold his own–he is smart and funny and, most importantly for me, he plays along. Sometimes I’ll start in with some kind of obvious nonsense and he’ll just keep feeding me material to see how long I’ll keep it up. He knows he’ll lose. I did improv for a while; I’m happy to die on the hill of the outrageous claim or premise. We make each other laugh, which I really think is the key to a lot in a long term relationship of any kind. Humor was always a requirement in any kind of romantic relationship for me. You have to be able to laugh at yourself most of all. And, to me, survival is wrapped up in your capacity to find the levity in the absurdity, mess, pain, and wonder that life wads up and chucks at you.

   

3. Was anyone ever threatened by your humor?

   I learned years later that my humor intimidated certain guys who might have wanted to ask me out, but didn’t. I also found out when I went through a stretch of being single before I met my, now, partner, that guys often said they wanted a woman with a great sense of humor, but what they really meant was they wanted someone to laugh at their jokes, not be funnier than them. I always that that was hilarious in itself–like how insecure can you be? You’re already a single, straight, white male–privilege jackpot! You require all the laughs, too? I don’t think so. Move along, pal.

4. Can you tell me about a time when you turned something painful into something humorous?

   Too many times to count, honestly. Here’s one: In July of 2001 I flew to New Orleans to see a guy I was in one of those on again/off again relationships with. I had a hunch that this was going to be it for the relationship, but was giving it one last chance. It predictably went terrible; we had a huge fight the night before I left. The next day my flight didn’t leave until something like 4 in the afternoon. I had showered and dressed and went into the living room and he goes “Ready?” And I just said “Yep.” I sort of expected one of us to blink in some respect. Nope. We drove in silence to the airport; he pulled up to the curb, took my bag out of the trunk and plopped it on the sidewalk, got back in the car and drove off. This was back when they had computer kiosks in the airport where you could get like 30 minutes of free Internet at a stretch, not that there was much ‘net to surf anyway. I found one of those and then I spent the day emailing different friends in 30 minute intervals about what had just happened. Each time it became more exaggerated and cartoonish in the telling until I essentially described him doing some kind of Andre The Giant move HURLING my tiny suitcase out of the car as he drove away, tires SQUEALING in the steamy New Orleans heat. Who says revenge is a dish best served cold? I say it’s best served up as an unflattering, hilarious SATIRE!

5. Can you describe the type of humor you possess? Clever Wit, quick-with-a-joke, physical, goofball, aggressive, self-enhancing, self-deprecating, dark, observational, or one I didn’t think of?

   I’d put myself in the clever wit, quick-with-a-joke/come back/funny rejoinder; also observational and silly. I love things that are a little absurd. I do have a hard time turning off my humor to be honest, so it’s always in play no matter my interactions. I can read a room or a dynamic and dial it way back, but it’s always just below the surface. This is a typical instance: The last time my husband and I had one of those pro-forma meetings with our financial planner person they were going over one of the spreadsheets and it included a line item for something referred to as CASHSWEEP. I sort of blurted: “Cashsweep? That sounds like some kind of game show! Hey everyone, who’s ready to play CASH! SWEEP!” I did it with a game show announcer voice and pumped up hand gestures and the whole nine yards and yadda yadda yadda now we have a new financial planner person.

6. Was your humor ever mean? What happened? Any regrets?

   Yes and yes. In high school. There is an episode of 30 Rock where Liz goes back to her high school reunion. In her recollection she was the girl everyone ridiculed. But it turned out that she was this sarcastic-funny-mean girl and everyone was afraid of her. I don’t think people were afraid of me, but I was that sarcastic-mean-funny girl. It was just a lot of pain I was suppressing. I was a colossal funny-mean-girl jerk to one girl in particular who would fight back with classic, old school insults. About five or six years ago she popped up on Facebook in another person’s comments. I just knew it was right to reach out to her. I messaged her and apologized for my behavior; not my best or even genuine self, just a sad-mad-teenage girl in pain she didn’t know how to deal with. The response was really lovely–gracious and forgiving and we’ve stayed in contact. This is why I only use my humor super power for good…..unless that comic retribution is EARNED.

7. What would be the title of your life right now?

   Keep Laughing and Carry On

Sheila is a humorist, author, photographer, lifelong New Englandaaahhh. She writes regularly on Substack with her publication, Humor Saves! (formerly Stay Curious). She is also the author of Boston and Beyond: Discovering Cities, Harbors, and Country Charms (Globe Pequot); The League of Extraordinarily Funny Women: 50 Trailblazers of Comedy (Running Press), and the forthcoming Book Lover’s New England: A Guide to Literary Landmarks (out in 2026, Globe Pequot). You can find her photography on Instagram (@wordnershe). You can find Sheila somewhere with a smirk on her face and something silly on her mind.

Now for comments, questions, or just love on Sheila. I’ll start.

1. Sheila is the first to confess that her humor was once mean. Love your honesty. I can remember offending a couple of girls in High School too. Apologies.

2. Any comedy books on the horizon?

3. What made you want to write tourism books?