Q & A with Jessi Cruickshank

Renowned for her humour, quick wit, and authenticity, Jessi Cruickshank has been called “the internet’s funniest mom” (Today’s Parent) and “Canada’s most followed television personality on social media” (Toronto Life). She is the creator of New Mom, Who Dis? the #1 digital series in the country on Facebook Watch and has hosted some of television’s most popular programs, including The Hills After Show, CBC’s The Goods, and Canada’s Smartest Person.

Jessi launched New Mom, Who Dis? in 2018 and it has since grown into a global online community and brand. It is a go-to destination for candid, honest, and always funny takes on motherhood. In 2022, Jessi hit the road with her first live, cross-Canada Stand Up Comedy tour, “Up Close and Too Personal”, which sold out across the country twice. Most recently, she launched her own weekly podcast series, Phone a Friend which debuted as the #1 comedy show across all podcasts.

Jessi is a mother to twin boys, Rio and Dray, and young daughter, Romi. She was born in Calgary, raised in Vancouver and now lives with her family in Los Angeles.

We’re so excited to bring you our Q & A with Jessi Cruickshank!

What does comfort mean to you?

Feeling totally relaxed and at ease physically and mentally and also having NO TOP BUTTON DONE UP…just letting the belly that birthed three children HANG OUT.

Are you team PJ set or team Nightie? And what's your pajama style of choice?

Always PJ set- I feel strongly about this. I don’t love a nightie creeping up into my bits at night. I love pants and a long-sleeved set in winter and a Tank or Tee with shorts in the summer.

What's the first thing you do when you walk through your door at the end of the day?

TAKE MY DAMN JEANS OFF. I am literally undoing the top button AS I WALK INTO THE HOUSE. The PJ bottoms or sweats go on immediately… then I kiss my kids. PRIORITIES.

What's the most important thing you look for in sleepwear?

I have a segment on my podcast called ‘What’s Giving Me Night Sweats’ because I actually DO sweat profusely at night thinking about all the things that give me anxiety. It’s not sexy but it’s true! So I need light weight, breathable sleepwear now more than ever.

Do you have a bedtime routine? If so, what do you do to prep for sleep?

LOL. For my kids? Absolutely - my toddler gets a warm bath, books, songs… my twins get a nice shower, they put on soft PJs, lotion story time… I have NO BEDTIME ROUTINE FOR MYSELF. Unless falling asleep while working in bed with my laptop open, counts?

We are big fans of your podcast, Phone a Friend. Who has been one of your favourite guests so far and what made that particular conversation so memorable or enjoyable for you?

I’m SO GLAD! The best part of doing this podcast is hearing from the people who listen to it - it feels like we have this secret club together - we have our own inside jokes… its like being on a private group chat with tens of thousands of people every week. I loved having Dan Levy on, obviously - I don’t think either one of us realized how excited people would get to hear us reunite for the first time publicly in over a decade.

I always love a celebrity guest - *NSYNC’s Chris Kirkpatrick was a personal highlight, as were the girls from Selling Sunset - but I also love the guests I have on who are viral sensations. I’ve called The Hot Wiggle, Taylor Swift’s Fake Security Guard and the Only Fans model who took down Piers Morgan on Live Television. I created Phone A Friend so I can phone someone to explain things that are happening in Pop Culture so those calls really are the best.

When was the last time you stayed in jammers all day (AKA the best day ever)?

My family was in Denver during the Christmas holidays and one day it snowed so hard, we cancelled our plans, stayed in jammies, baked gingerbread houses and watched holiday movies all day- it was HEAVEN. I think my kids actually remember that day more than anything else we did during the break!

What is one of the most valuable lessons or insights you've gained from your experience as a mother to your twin boys and young daughter?

I’m still learning!  But I think something I try to remember daily is that you can’t do it all, you can only ever do your best. I am someone who always tries to be the best at my job and be the perfect mom and sometimes I beat myself up when I can’t be all of those things all at once. Having three kids 5 and under has been a real lesson in letting go and accepting help when I need it. (and I ALWAYS NEED IT).

At what time of day do you get your best work done?

When I first get to the office after dropping all three kids off at school - that first hour at my desk is always SO productive. The middle of the day is a mess of zoom calls and shoots and school pick ups… but then I get productive again when all three kids are asleep. I put on my This Is J PJ’s, open my laptop in bed and work until I fall asleep. 

I know, I know I’m supposed to relax, unwind and have ‘me time’ but when you’re a working mom trying to balance a full-tilt career AND be there for your kids, it’s usually not possible. I have to work in the slivers that I have!

What has been the most memorable or rewarding experience from your recent live tour, "Up Close and Too Personal", across Canada?

I think that tour was the pinnacle of my career so far. I have worked so hard to establish myself in the comedy world, and I have truly grown up with the audience who came to see me, so it really felt like 15 years of work culminated with that tour. 

Plus, it happened on the tail end of the pandemic - it was my first time travelling and leaving my house in over 2 years and I didn’t realize how badly I needed to laugh and connect with like-minded people. I think my audience felt the same way - it was the best night out everyone had in YEARS. Literally! 

Can you tell us about any exciting projects or upcoming endeavours you're currently working on in your career?

My podcast, Phone A Friend, has really blown up in a way I NEVER EXPECTED IT TO and I have been loving the thrill and challenge of figuring out this new medium. I am going to the Just For Laughs Festival this summer to do an episode LIVE which I am terrified/excited about. I also just launched a collaboration with Os and Oakes - a small Canadian clothing company I love and it has been thrilling to see those pieces sell out. Plus! I have promised I’ll go on tour again… nothing announced yet but follow me @jessicruickshank for announcements!

Are you a go out and dance on tables or stay in and stay cozy type of person?

LOLOLOL. I used to be a dance on tables kind of gal.. now I am definitely a stay cozy type of person

We love that you've been a fan of our Bamboo Jammers since 2018. How many pairs of This Is J PJs do you own? What style is your favourite?

YES! At this point I probably have 10 pairs of This Is J PJs, I know, I have a problem. And the crazy thing is I literally still wear my 6 year old This Is J jammies nightly - the quality is so good, they don’t wear out! I actually passed on two pairs of my twins’ This Is J sleepers to my baby daughter 5 years later and they still look brand new on her!

I have tons of the Henley Harem sets (which have been great for breastfeeding) I also love the Tank sets for summer (/night sweats!) and I do have a matching robe or two!

If you could go back and give your 18-year-old self one piece of advice, what would it be?

I’d probably tell myself “PSST… you’re never gonna be that cool, hot blonde girl on Much Music so stop trying. Just be you and trust that it will be enough.” Because, hey… it kind of was!

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