Going into business with your best friend sounds like a dream—but how do you protect the friendship when work, stress, and different expectations get involved?

This week on The Art of Classiness, Robin and Deborah are celebrating 100 episodes—and the fact that they are still friends. They share what building a podcast together has taught them about boundaries, honest communication, creative disagreements, and putting friendship first.

In this special anniversary episode, they go back to the beginning: what they thought they were creating, what they completely underestimated, and the “classiest blunders” they can finally laugh about now. They also unpack the friendship-first principles that have helped them keep going: dream big, protect mental health, stop keeping score, say the hard thing while it is still small, and assume good intent.

It’s an honest, funny look at building something with a friend—and making sure the friendship has room to grow alongside it.

Here’s to 100 episodes. Here’s to still being friends. And here’s to 100 more.

Connect with us on Instagram and TikTok: @artofclassiness
Share your favorite AOC moment—or what you want from the next 100 episodes: artofclassiness@gmail.com

Quick disclaimer, friends—we are not business coaches, therapists, or relationship professionals. We are two friends sharing what has worked for us while building something together. This episode is for fun and informational purposes only. Take care of yourselves, communicate clearly, and use what feels right for you.

Menopause is about so much more than hot flashes, and “that is just aging” is not an acceptable answer. In another This Episode Will Piss You Off, Robin and Deborah talk about the things women are too often expected to endure quietly.

Deborah unpacks menopause and the fact that declining estrogen can affect far more than hot flashes. We talk about why women are not given better information about their bodies, why female sexual health remains under-discussed, and why “that is just aging” is not an acceptable answer.

Robin explores abortion bans and pregnancy emergencies through the stories of women with wanted pregnancies who needed urgent medical care when things went wrong.

This episode includes discussion of menopause, painful sex, pregnancy loss, sepsis, abortion restrictions, and maternal death. Please take care of yourself while listening.

Sources:
Effects of pelvic floor muscle training on sexual function of postmenopausal women

ACOG

Menopause Society

Women’s Health Initiative (WHI)

FDA Approves Labeling Changes to Menopausal Hormone Therapy Products

DISPARITIES IN FUNDING BETWEEN MALE AND FEMALE SEXUAL FUNCTION-RELATED DISORDERS

National Network of Abortion Funds

KFF Abortion in the U.S.

Reproductive Freedom for All

Say Their Names: The Women Who Died After Being Denied Emergency Abortion Care

A Pregnant Teenager Died After Trying to Get Care in Three Visits to Texas Emergency Rooms

Woman said she went into sepsis before she could get lifesaving abortion care in Texas

Life of the Mother: How Abortion Bans Lead to Preventable Deaths

Texas Medical Board Sanctions Three Doctors for Delayed Care That Led to the Deaths of Two Pregnant Women

Class Act of the Week: Jay Filmore: Pink Pill RX

Quick disclaimer, friends—we are not doctors, lawyers, or mental-health professionals, just two people who love to share ideas and experiences. This podcast is for fun and informational purposes only. It's not meant to replace professional medical advice, diagnosis, or treatment. If you have questions about your health, definitely reach out to your doctor or a qualified health professional. Take care of yourselves and use what feels right for you.

Not every mental health day looks the same. Sometimes you need to sleep, sometimes you need to get out of your own head, and sometimes you need to be around someone who makes you feel like yourself again.

In this episode, we’re breaking down five different kinds of mental health days: I’m Drained, I’m Overwhelmed, I’m Hurting, I Need Connection, and I’m at a Crossroads. We talk about recognizing what you actually need, giving yourself permission to step back, and knowing the difference between rest, distraction, connection, and avoidance.

Plus, we tackle a Class or Crass scenario about whether it’s fair to feel resentful when someone else takes a mental health day while you’re drowning in your own responsibilities.

So take what you need from this episode. Rest, connection, perspective, or permission to do a little less for a day.

Connect with us on Instagram and TikTok: @artofclassiness
Send us your own “too old to pretend” list: artofclassiness@gmail.com

Quick disclaimer, friends—we are not doctors, therapists, or professional event planners. We are two women with opinions, a deep respect for seating, and a healthy skepticism of any event requiring a group Venmo. This episode is for fun and informational purposes only. Take care of yourselves and use what feels right for you.

Brunch lines, baby showers, music festivals, and any event requiring a group Venmo: Robin and Deborah are getting honest about the things they are officially too old to pretend they enjoy.

Not because they are against fun. Not because they want to stay home forever. And definitely not because anyone needs permission to enjoy brunch, a baby shower, a music festival, or a chaotic group chat. But at a certain point, adulthood teaches you that being “easygoing” does not have to mean ignoring your own preferences, spending money you do not want to spend, standing in lines you do not want to stand in, or forcing yourself through social rituals that leave you more depleted than connected.

Along the way, we ask: Is saying no to an invitation selfish—or is it respecting your own time? When does an “experience” become a logistical nightmare? What is still worth a little inconvenience? And which millennial staples are we keeping, retiring, or defending forever?

Connect with us on Instagram and TikTok: @artofclassiness

Send us your own “too old to pretend” list: artofclassiness@gmail.com

Quick disclaimer, friends—we are not doctors, lawyers, or mental-health professionals, just two people who love to share ideas and experiences. This podcast is for fun and informational purposes only. It's not meant to replace professional medical advice, diagnosis, or treatment. If you have questions about your health, definitely reach out to your doctor or a qualified health professional. Take care of yourselves and use what feels right for you.

This week on The Art of Classiness, Robin and Deborah are back in the AITA universe to talk grief, family boundaries, entitlement, and the difference between asking for support and expecting access.

A husband wants to leave for a hockey game after his wife’s grandmother dies. A new mom faces family drama over who gets to meet her baby first. A mother-in-law refuses to hire her daughter-in-law at the family business, and a cruise guest wants an amazing deal—without following the rules that come with it.

Connect with us on Instagram and TikTok: @artofclassiness
Share your stories, hot takes, and verdicts: artofclassiness@gmail.com

Quick disclaimer, friends—we are not doctors, lawyers, or mental-health professionals. We are two people who love to share ideas and experiences. This podcast is for fun and informational purposes only and is not a substitute for professional advice. Take care of yourselves and use what feels right for you.

When does family become entitled? When is “being the bigger person” just another way of asking someone to ignore their own needs? And how do you set a boundary without becoming the villain in someone else’s story?

Gossip, hysteria, the color pink, and red lipstick seem totally unrelated—until you trace how each one became tied to women, femininity, and the endless cultural pressure not to be “too much.” Robin and Deborah are going historical.

First, we get into the surprising origins of gossip: a word that once referred to close, trusted companions before it became shorthand for petty, malicious, feminine talk. Then we unpack hysteria, the ancient medical idea that women’s bodies and emotions made them unstable, and why the language of “dramatic,” “hormonal,” and “too sensitive” still hits differently today.

We also look at how pink became a gender rule rather than just a color, why the pink-for-girls/blue-for-boys divide was never as natural or universal as we were taught, and how consumer culture helped turn color into a personality category.
Finally, we trace the long, complicated history of red lipstick—from ancient pigments and moral panic to glamour, suffrage-era visibility, confidence, rebellion, and the modern question of why one color on a woman’s mouth can still make people have opinions.

Join us for a conversation about history, womanhood, cultural rules, and all the weird things society decided women should be judged for.

NPR: ‘Gossip’ had godly origins. Here’s how it gained its sinful reputation

Connect with us on Instagram and TikTok: @artofclassiness

Share your thoughts and stories: artofclassiness@gmail.com

Quick disclaimer, friends—we are not doctors, lawyers, or mental-health professionals, just two people who love to share ideas and experiences. This podcast is for fun and informational purposes only. It's not meant to replace professional medical advice, diagnosis, or treatment. If you have questions about your health, definitely reach out to your doctor or a qualified health professional. Take care of yourselves and use what feels right for you.

Not every friendship needs a dramatic breakup. Sometimes, someone simply needs less access.

This week on The Art of Classiness, Robin and Deborah are talking friendship circles: who gets a front-row seat to your life, who gets the group-chat version of you, and when someone may need to move from your inner circle to the outer one. They unpack the signs that a friendship has become unbalanced, draining, untrustworthy, or held together by one person doing all the work.

They also share practical ways to create distance without becoming cold: changing the frequency, depth, or setting of the relationship; shifting from one-on-one time to group hangs; and protecting your time, energy, and vulnerability without punishing anyone.

Because friendship is not all-or-nothing. You can care about someone and still decide they no longer get the closest version of you.

Class Act of the Week:
Reina Condos

Circle of Friends Worksheet

Connect with us on Instagram and TikTok: @artofclassiness
Share your thoughts, stories, and verdicts: artofclassiness@gmail.com

Quick disclaimer, friends – we're not doctors, just two people who love to share ideas and experiences. This podcast is for fun and informational purposes only. It's not meant to replace professional medical advice, diagnosis, or treatment. If you have questions about your health, definitely reach out to your doctor or a qualified health professional. Take care of yourselves and use what feels right for you.

Confidence is not about being perfect, fearless, or the loudest person in the room. It is about trusting yourself enough to take up space, make decisions, recover from mistakes, and keep going when you feel unsure.

In this Classy Care episode, Robin and Deborah break down five habits that can quietly destroy confidence and self-worth: negative self-talk, poor body language, toxic relationships, people-pleasing, and constantly seeking validation from everyone else.

They also share practical, realistic ways to build confidence back up—from changing the way you speak to yourself and setting cleaner boundaries to taking up your reasonable amount of space and creating your own internal scorecard.

Plus, they discuss the famous “power pose” study, what later research did and did not support, and why standing a little taller may still help you feel more grounded before a hard conversation, meeting, or moment.

Connect with us on Instagram and TikTok: @artofclassiness
Share your thoughts and Classy Care wins: artofclassiness@gmail.com

Quick disclaimer, friends – we're not doctors, just two people who love to share ideas and experiences. This podcast is for fun and informational purposes only. It's not meant to replace professional medical advice, diagnosis, or treatment. If you have questions about your health, definitely reach out to your doctor or a qualified health professional. Take care of yourselves and use what feels right for you.