Why does humor matter in parenting?
Well, because.
Okay, perhaps a question like that deserves some more attention.
writes on Substack. I routinely find myself laughing in the darkness of my kitchen (#LITDOMK, let’s make it a thing). Shelly captures the ridiculous of motherhood, aging, friendship and more with both raw humor and a kind understanding that life stuff can be hard. Shelly “is the award-winning author who writes about the humorous side of parenthood and middle-aged and sometimes Dungeons & Dragons. She's complicated, okay?” And it is a great joy to bring this interview here on A Wonderful Mess.When Shelly sent me her answers, she noted the length and said we could work on making it shorter. I chose to keep the length because as I read I smiled, laughed and was inspired to organize a moms’ Dungeons and Dragons group. But most of all I felt connected and hopeful—and I believe that is the power of humor. You need people around you on this wild adventure of parenthood who make you laugh…and have the good snacks. So get a good snack and get ready a wonderful interview.
Note: The interview occurred through email and has been lightly edited.
Tell us a little bit about you and your family.
Shelly: My husband Bart and I met at work and were best friends for 5 years before we started dating. We liked each other so much (platonically!) we tried fixing each other with our friends. Thankfully none of those connections went past the first date because our wedding would have been super awkward. We’ve been married now for 13 years and have an 11-year-old son who is pretty much the greatest human ever to grace the planet (according to 3 out of 4 grandparents.) We also have a beautiful dog named Penny who has garnered more Substack love than I have. Right before her adoption was finalized I posted her photo and a note saying how excited we were to welcome her home and it got over a thousand likes. Everyone thinks cats rule the internet, but Penny begs to differ!
You write the hilarious Middle-Aged Lady Mom Substack, what brought you to write your newsletter? What have been your favorite things to write about?
Shelly: I’ve had a website for years that I barely updated and never figured out how to use any of those site traffic widgets so basically, I was just writing into the void. Was anyone out there? Who knew? I did get a ton of comments from “web designers” who “stumbled onto my site”and wanted to “help me reach my goals” and helpful strangers looking to deliver porn right to my inbox, so I didn’t have to “search for the good stuff all over the internet” which, you know, was very kind, but probably not my target audience.
I don’t remember how I discovered Substack or realized it was a platform I could be on, but I do remember telling a friend one day, “I’m joining Substack and starting a newsletter!” and speaking it made it so.
My entry into motherhood wasn’t smooth. Those early months were dark and depressing (kind of like “searching the internet for the good porn”) and I felt woefully unprepared despite all the classes I took and blogs I read. Worse, I felt alone. Like I couldn’t tell anyone how much I was struggling because everyone kept saying how magical motherhood was supposed to be and how happy and excited I surely was. Guess what? They LIED! It was hard for them too, but they either blocked it out or shut up because they didn’t want to scare me.
Apparently, I do want to scare new parents, but only so they don’t feel like lonely, little failures. Misery loves company, right? Those dark, scary feelings are pretty common, especially for new moms so I also want to make them laugh. The more we talk about the challenges, the more we can normalize them and the more “normal” it becomes, the less afraid someone might be to ask for help.
While I love slandering the reputation of newborns, lately I’ve been dabbling more into middle-aged lady humor because WOW—our bodies are just an endless font of chuckles, and I find that laughing really helps alleviate this constant gas and bloating.
When and how did Dungeons and Dragons (D&D) come into your life? And can you give a brief lay of the land for someone who has never experienced D&D before?
Shelly: Yes! D&D is a collaborative storytelling game. One player takes on the role of Dungeon Master (or DM) who is essentially the narrator of the story. The rest of the players create heroes who explore fantasy worlds together, embark on epic quests, fight monsters, level up, reap great rewards, and possibly save the world. The story is up to the players and DMs so you never know what direction it will take and that’s where the real magic happens. It’s social, creative, imaginative, and has the power to form lifelong friends beyond what happens around the table. Imagine it’s like your weekly book club or poker night only with swords, fireballs, and possibly a dragon.
One might say D&D came into my life because my boss forced me to play it! I’ve worked for the game’s publisher for over 20 years now and many of those years were working on the Dungeons & Dragons brand. My boss rightfully figured I should probably learn how to play the game I was being paid to promote. I resisted because even though I was surrounded by people who designed, played, and loved this game who seemed perfectly “normal” (honestly, a little disappointing really. I expected more accents and long, gray beards), I harbored some dated, old stereotypes. No way would someone like me (girly-girl, bad at math, not a fantasy fan, scared of improv) play a game like D&D! About six minutes into my first game, I realized how wrong I had been. It’s been love ever since!
D&D is just hanging out with people you enjoy, pretending to be a way cooler version of yourself, making up stories, and creating memories. Pretty much what my friends and I did every weekend! There is something to love about this game no matter who you are, what you’re into, or how bad at math you think you are. (HINT: There’s a ton of digital dice rollers that add everything up for you.)
Beyond your newsletter (and the many other things you do), you are a published author and podcaster, now releasing your fourth book, can you share a little bit about your books?
Shelly: Are you ready for some really long subtitles? Because I’m about to deliver. I’ve written four books about Dungeons & Dragons and no one is more surprised by that than me. I’m endlessly fascinated by how this 50-year-old game has remained so relevant and influential in gaming and pop culture and is still going strong! Each of my books has attempted to figure out that special sauce and why fans of D&D never stop being fans.
My first book Confessions of a Part-Time Sorceress: A Girl’s Guide to the Dungeons & Dragons Roleplaying Game was part how-to play and part personal essays about my discovery of D&D. Then came Everything I Need to Know I Learned from Dungeons & Dragons: One Woman's Quest to Trade Self-Help for Elf-Help, I attempt to live like my D&D character in my quest to have a more fulfilling life and become a better human. The third, Welcome to Dragon Talk: Inspiring Conversations About Dungeons & Dragons and the People Who Love to Play It, co-authored by my friend, Greg Tito, recounted some of our most inspiring interviews from Dragon Talk, the official D&D podcast. And finally, the fourth book comes out this November and is the epitome of my worlds colliding. HOW TO DUNGEON MASTER PARENTING: A GUIDEBOOK FOR GAMIFYING THE CHILD-REARING QUEST, LEVELING UP YOUR SKILLS, AND RAISING FUTURE ADVENTURERS* uses the tenets of D&D’s most beloved players to teach parents and parents-to-be how to (Dungeon) master parenting. I love this book. Am I allowed to say that? Because I really do. The writing process was very much like reliving the stages of parenthood from catering to a newborn (The long nights! Where do I even start? This will never end!) to a toddler, (Hey, this thing has a mind of its own, but maybe I’m starting to get the hang of it?) to a tween (It has a personality! And I kind of like it!). If you are looking for atypical parenting “advice” with a dose of humor written by someone who has set the parenting bar so low a baby could climb over it, this is your book! No prior knowledge of D&D needed!
Did actor Joe Manganiello blurb your third book? (this seems like good bar trivia about Shelly)
Shelly: Not only did he blurb my third book, but he referred to Greg and I as the “Regis and Kathie Lee of Dungeons & Dragons!” Is there a greater compliment? I don’t think so. Joe has been a guest on Dragon Talk and is a HUGE D&D fan. He used to visit our office often and would geek out like the rest of us. Just a totally normal day around the office!
Why does humor matter in parenthood and how do you think it can support parents (or human beings in general)?
Shelly: Humor is VERY important in all of my relationships! My favorite people are funny people. What a gift it is to make someone laugh! So really, my favorite people are people who think I’m funny.
As mentioned, my husband, Bart, has a great sense of humor and thank goodness for that because I often write about him. I also credit his humor with how we’ve managed to stay married. I’m not always easy to live with. As a middle-aged lady my moods can be a bit…swingy. There have been several times when he could have absolutely and justifiably lost his patience or engaged in a spat, but instead he’ll say something funny, catching me off guard and I realize how ridiculous I’m being. Things would be much different in this house if he didn’t have the ability to laugh in or at the face of danger! (It’s me, I’m the face of DANGER!)
There are plenty of serious, stressful, anxiety-inducing moments in parenting so a sense of humor is a must. Laughing relieves stress, alleviates awkward situations, can lighten uncomfortable social interactions, and create bonds. You don’t have to be funny ha ha to add humor to your parenting. You can do funny things—spontaneously jump into a pile of leaves, make up voices for the stuffed animals, create a super elaborate, secret family handshake. (I can personally attest to all of these things being great mood enhancers, especially when the neighbors are watching.)
When my son was little and learning to regulate his emotions, I told him I could pull bad moods out of his ears. Whenever he was on the verge of a meltdown I would look in his ear and say, “I see it! Do you want me to get it out?” And we’d create this huge spectacle removing that bad mood like a magician pulling a string of scarves out of their sleeve. It usually snapped him out of it. Thankfully the child loves a good bit as much as I do.
There were so many times as parents where my husband and I were about to lose it, or scream into a pillow for a few hours, or take a long walk and come back in two years, and thankfully found the humor instead. One time, our then toddler was sick and we were all sleep-deprived so in our desperation we let him have a middle-of-the night bath with dad. (I even let him use my fancy lavender infused body wash hoping it would make him sleepy!) When my husband was getting out of the tub I made some comment about his butt (because I am a middle-aged woman going on 7-years-old) and our son said he also wanted to see “Daddy’s butt.” Like, refused to get out of the tub until he saw Daddy’s butt. I can still hear his little voice crying, “I can’t see it! I can’t see, Daddy’s butt! Let me see it!” I mean, what are we supposed to do at that moment except laugh? We just wanted him to calm down, feel better, and go to sleep. Should Bart have shown him his butt? Was that appropriate under the circumstances? Will he just go to sleep if daddy moons him??? (There’s definitely a Goodnight Moon joke in here somewhere.) I’m telling you, that story comes up at least once a week. It’s one of our favorites. If someone utters the words, “I can’t…” everyone else will shout, “SEE DADDY’S BUTT!”
Our family has collected so many funny stories like “Daddy’s Butt” (which is great news for anyone who reads my newsletter) and each time one of those stories gets told again, I feel our bond growing stronger. Storytelling as a form of human connection is an ancient art. Can’t you just picture cave moms and dads drawing pictures of colicky newborns and being like, “WTH is this thing? And we thought pterodactyls were loud???”
Humor also teaches us to laugh at ourselves and that is an amazing skill. It’s great for building resistance, boosting self-esteem, making the environment less tense, and showing kids that everyone makes mistakes and they’re no big deal. I often tell my son this: If (or really when) you do something mortifying or if you feel like someone else is trying to embarrass you, be the first one to laugh. Even if you don’t think it’s funny. (“Fake it til you make it” is also big around here.) To use a very common reality TV trope, control your narrative. The power is yours now. And people will laugh with you, not at you.
Incidentally D&D is really good at making “failure” fun and giving kids permission to take risks in a safe and supportive environment. They will try amazing, creative, preposterous things even knowing there’s a low success rate, because they realize that “failure” is where some of the best, most memorable, funny stories come from. The same can be said about parenting. Oh, you’ll definitely have moments of failure and you can’t even blame a low dice roll! If you and your partner can laugh your way through a major blowout or projectile vomit or packing your kid up for college, you’re doing something right.
What or who makes you laugh? In your opinion, what makes something really funny?
Shelly: My favorite kind of humor is observational humor. I love finding the funny in mundane things. Curb Your Enthusiasm for obvious reasons remains one of my favorite shows.
I laugh and butts, farts, poop, balls— maybe because I’m around so many 11-year-olds?
Unfortunately, I also laugh at inappropriate moments so I will be in absolute hysterics if someone trips and falls on the sidewalk or steps on a Star Wars action figure while carrying a very full laundry basket. (“IT WAS A JAWA” is also a classic family story.) I’m not great at helping in a crisis, but it is where I'll deliver some of my best material.
Besides my husband, my son is one of the funniest people I know and THANK GOODNESS for that. I don’t know what I would do if I had an unfunny kid. He has natural comedic timing and a sharp wit. He observes and remembers everything so he’s always ready with a call-back and he does amazing impressions. He can imitate both Bart and I with eerie precision which would be super annoying if it weren’t so funny and spot on. He’s also becoming a very good writer so look for his Substack coming in 2032!
Does your family appreciate your humor?
Shelly: They better! I mean, I like to think I’m good for a laugh once in a while.
The other day I was driving my son and his friend to basketball practice and I made a joke. My son, apparently incredulous, said, “Damn, my mom is actually funny.” I think there’s still this perception that women, especially MOMS, can’t be funny. You think the Finder of Lost Things and Maker of Lunches can’t also drop some witty banter on the basketball court? Because I have news for you, kid!
I grew up with funny parents. Our house was full of laughter thus making it the home everyone gravitated to. My parents appreciated each other’s sense of humor and encouraged mine. My mom and dad met in college and she always said she heard my dad before she saw him. Apparently he was very loud and gregarious and always in front of a very receptive audience. She was definitely won over by his sense of humor. My mom was also a great entertainer. She could come up with an entire song (that rhymed even!) on the spot about literally any topic— my stuffed animals, a neighbor, Wheel of Fortune. I think my humor is a blend of each of them. We didn’t discover my brother was funny at all until he was in his 20’s. His nickname used to be Old Stoneface because he didn’t show emotion until he was three-years-old. Turns out, he is funny, just in a much more subtle way.
What are your thoughts about building community through humor?
Shelly: The world is challenging to say the least. Being able to surround yourself with happy, positive, funny people isn’t just good for the soul, it’s mandatory! We all need a good laugh.
The cliche “laughter is the best medicine” is cliche for a reason. Being around funny people can have a profound impact on your mood, mental health, and well-being. Now that my son is in middle school he’s meeting more people and making new friends. When I ask him what draws him to these kids he almost always answers, “They’re funny.” I think it’s very natural to be attracted to a funny person or someone who can lift our spirits with a good story. It also feels pretty good to make someone laugh.
If none of your friends are funny, but you always have someone to hang out with, congratulations— you’re the funny one. Keep up the good work! Your friends, especially the ones who are parents, need you!
Thank you to Shelly for hanging out in the mess and making it a better, funny place to be.
You can find
at . You can purchase her upcoming book here. Go on, do it.
Great interview! I learned so much more about you, Shelly, which was awesome. I didn't think it was possible for me to like you more, but dammit, here we are.
Thanks to you both!
LOVED this interview. It perfectly illustrates why Shelly and I are best friends (who’ve only met twice). ❤️