Lifestyle, Relationships Cailyn and Gillian Lifestyle, Relationships Cailyn and Gillian

Episode 99: Asking for a friend: how do I date my damn self?

It’s officially the month of love (and the unofficial Miley-buy-yourself-flowers month!), so we’re kicking it off with an episode dedicated to the real love of our life – ourselves! It’s easy to get so focused on dating and romance, that we forget about the importance of self-love, and we’re ready to change that.

Whether you’re feeling lonely or single, or craving some you-time in your relationship, learning to date yourself is a practice that can literally change your life. Because the way you treat yourself will impact the love you attract and the future fulfillment you feel. 



It’s officially the month of love (and the unofficial Miley-buy-yourself-flowers month!), so we’re kicking it off with an episode dedicated to the real love of our life – ourselves! It’s easy to get so focused on dating and romance, that we forget about the importance of self-love, and we’re ready to change that.

Whether you’re feeling lonely or single, or craving some you-time in your relationship, learning to date yourself is a practice that can literally change your life. Because the way you treat yourself will impact the love you attract and the future fulfillment you feel. 

And this isn’t just for the singles! Learning to fulfill your own needs, take yourself out, and romanticize your day-to-day will positively affect all your relationships, and it starts with showing up for your damn self. Luckily, Gill has been on a self-love journey through singledom and solo living, and she’s here to spill the tea on everything she’s learned along the way. 

So if you’re ready to enter your Miley era, join us as we chat about:

  • What dating yourself *actually* means

  • Why it’s time to stop putting your life on hold

  • Reclaiming your alone time and reframing loneliness

  • How to take yourself on a solo date 

  • Ways to romance yourself in the day-to-day

  • Why you should be giving yourself your love language 

  • The deep inner work that will increase self-compassion and self-love 

We hope this episode inspires you to hold your own damn hand and start prioritizing YOU! If you have any burning questions for us and you want to get us in the hotseat, DM or email us your Qs at contact@teachmehowtoadult.ca and we’ll dive into them in an upcoming Asking For A Friend. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More
Wellness Cailyn and Gillian Wellness Cailyn and Gillian

Episode 80: How To Find Yourself After A Big Life Change

It’s true what they say: Change is the only constant. From parenthood to career pivots, big moves to breakups, big changes are unavoidable, but they can leave us feeling lost and totally destabilized.

So in this week’s quickie we’re diving into life’s big transitions, and how to find ourselves (maybe even a more evolved version of ourselves) on the other side. Every change is a chance to recalibrate, so let’s get comfortable with being uncomfortable, and figure out how to come back to yourself when you’re finally through the turbulence.



It’s true what they say: Change is the only constant. From parenthood to career pivots, big moves to breakups, big changes are unavoidable, but they can leave us feeling lost and totally destabilized.

So in this week’s quickie we’re diving into life’s big transitions, and how to find ourselves (maybe even a more evolved version of ourselves) on the other side. Every change is a chance to recalibrate, so let’s get comfortable with being uncomfortable, and figure out how to come back to yourself when you’re finally through the turbulence. 

Tune in as we chat about:

  • Leveraging change into growth opportunities

  • Cailyn’s big transition into motherhood

  • Taking time to grieve your old life

  • How to visualize a new chapter

  • Creating an action plan to help you get back to yourself

  • Finding joy and romanticizing your life

  • The importance of hobbies and passions

  • Easy ways to shake up your life when you’re stuck

We hope this episode helps you on your journey to finding yourself again. You’ve got this. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More
Wellness, Relationships Cailyn and Gillian Wellness, Relationships Cailyn and Gillian

Episode 79: How To be More Honest

The one where Cailyn and Gill get realll honest about honesty… and it’s a juicy, therapeutic and vulnerable ride. Because let’s be honest: It isn’t always easy to tell the truth — to ourselves or to others.

Whether you’re struggling to have honest conversations, to admit the truth (to yourself or others), or you tend to hide things that are uncomfortable, it’s true what they say: The truth will set you free, and allow you to live your life unapologetically.



The one where Cailyn and Gill get realll honest about honesty… and it’s a juicy, therapeutic and vulnerable ride. Because let’s be honest: It isn’t always easy to tell the truth — to ourselves or to others. 

Whether you’re struggling to have honest conversations, to admit the truth (to yourself or others), or you tend to hide things that are uncomfortable, it’s true what they say: The truth will set you free, and allow you to live your life unapologetically.

This week we’re diving into our own journeys with honesty, how fear and shame can hold us back, how figuring out who you really are will help you live more honestly, and when it might be okay to tell a little fib. Buckle up, because we’re going deep.

Tune in as we chat about:

  • Different kinds of lies and the toll they take on our health

  • The motivations behind being dishonest

  • How being honest with ourselves is the first step

  • Owning who you are and what you really want

  • How shame and fear influence honesty

  • Accepting that you won’t have the answer to everything

  • The freeing benefits of radical honesty

  • When it’s appropriate to tell a white lie

We hope this episode helps you get real with yourself, who you are and how you feel, for a freer, more connected life!


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More
Wellness Cailyn and Gillian Wellness Cailyn and Gillian

Episode 72: Teach Me How To Love My Body And Cultivate Confidence, with Roxy Earle | Summer Rewind

For the rest of the summer, we’re doing a Summer Rewind, re-releasing some of our must-listen episodes as we ramp up to the launch of season two. See you in September friends!

Summer can be a very triggering time for a lot of people when it comes to body image and insecurities. We polled you guys on Instagram about how you’re feeling in terms of confidence and self-acceptance, and we learned that we’re definitely not alone in this feeling. 76% of you said that summer triggers your insecurities, while 77% of you are feeling anxious about re-emerging from lockdowns with all the physical and mental changes we’ve undergone. 91% of you said that you struggle with negative self-talk, and we feel you...we can all be our own worst critics and bullies.



For the rest of the summer, we’re doing a Summer Rewind, re-releasing some of our must-listen episodes as we ramp up to the launch of season two. See you in September friends!

Summer can be a very triggering time for a lot of people when it comes to body image and insecurities. We polled you guys on Instagram about how you’re feeling in terms of confidence and self-acceptance, and we learned that we’re definitely not alone in this feeling. 76% of you said that summer triggers your insecurities, while 77% of you are feeling anxious about re-emerging from lockdowns with all the physical and mental changes we’ve undergone. 91% of you said that you struggle with negative self-talk, and we feel you...we can all be our own worst critics and bullies.

That’s why we called in body positivity activist and the Queen of confidence, Roxy Earle. We’re on a mission to help everyone (including ourselves) positively develop the single most important relationship we’ll ever have — our relationship with ourselves. And that requires unconditional self-love, compassion, gratitude and some helpful tools to get us out of negative spirals when we’re struggling with our self-esteem or body image.

Roxy is a former marketing professional turned model, entrepreneur, body positivity activist and a star on Real Housewives of Toronto. She started the #MySizeRox movement, which advocates that confidence comes in all shapes and sizes. She’s worked with brands like Knix, H&M, Le Chateau and Joe Fresh to bring more inclusive sizing and styles to their stores, and is launching the Ana App, which is a tool to increase positivity & confidence while also optimizing your health.

Join us as we chat about:

  • Gill’s mindset shift for dealing with negative spirals, finding pride and respect in herself, and abandoning clothing sizes

  • Cailyn’s newfound outlook on self-love & body image as a soon-to-be mom

  • The moment that inspired Roxy to start the #MySizeRoxs movement

  • How confidence became her secret sauce and how to cultivate it (hint: it’s not genetic, it’s accountability!)

  • Roxy’s tips for practicing positive self-talk and self-love daily

  • Why Roxy is advocating for inclusivity and representation in the fashion industry

  • How a gratitude practice can help you combat insecurities and change your life

  • Why filters and body contouring apps are unattainable, exhausting and quite honestly...boring!

  • The mindset shift to have a healthier relationship with your body

  • The importance of practicing and modelling self-love as a parent

  • The #1 tip for looking and feeling your best in photos

    We hope this episode inspires you to wear the damn shorts this summer and to start loving yourself unconditionally. You deserve it. And if you need any support on your self-love journey, we’re here for you.


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More
Relationships Cailyn and Gillian Relationships Cailyn and Gillian

Episode 59: Teach Me How To Level Up My Love Life With The Five Love Languages

Love week is right around the corner so we’re throwing it back to this gem from 2021 where we dive into the five Love Languages, what they mean, and tips for dating each type.

ICYMI, The Five Love Languages was written by marriage counselor, Dr. Gary Chapman, and has sold over twelve million copies worldwide! We’re not kidding when we say it’s been a game changer for people all over the world…it’s literally been on the New York Times best-sellers list since 2007!

Dr. Chapman noticed that couples often came to him with the same concern: “I feel like my partner doesn’t love me.” Starting to recognize a pattern, he discovered that there were five categories on how people could give their partner the love they need: Words of Affirmation, Quality Time, Receiving Gifts, Acts of Service and Physical Touch.



Love week is right around the corner so we’re throwing it back to this gem from 2021 where we dive into the five Love Languages, what they mean, and tips for dating each type.

ICYMI, The Five Love Languages was written by marriage counsellor, Dr. Gary Chapman, and has sold over twelve million copies worldwide! We’re not kidding when we say it’s been a game changer for people all over the world…it’s literally been on the New York Times best-sellers list since 2007! 

Dr. Chapman noticed that couples often came to him with the same concern: “I feel like my partner doesn’t love me.” Starting to recognize a pattern, he discovered that there were five categories on how people could give their partner the love they need: Words of Affirmation, Quality Time, Receiving Gifts, Acts of Service and Physical Touch.

And these don’t only apply to romantic relationships. You can also practise self-care for yourself using the 5 love languages, and use them to form stronger relationships with your friends, family and coworkers!

Listen to our chat to learn more about:

  • How to practice self-care using the 5 love languages

  • The importance ‘Words of Affirmation’ play in making you feel understood

  • How to spend ‘Quality Time’ together when you see each other 24/7 or are in a LDR 

  • Why ‘Receiving Gifts’ isn’t as superficial as it soundsHow ‘Acts of Service’ can make your partner’s day

  • Why ‘Physical Touch’ is more than just sexy time

  • Two easy ways to find yours and your partner’s love language

  • Cailyn’s top love languages and how learning them made her relationship thrive

  • Gill’s top love languages and how they can change throughout her life


We hope this episode helps you tap into your love language for you and the people you love! 

Mentioned in this episode:


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More
Wellness, Lifestyle Cailyn and Gillian Wellness, Lifestyle Cailyn and Gillian

Episode 40: How To Love Yourself More

If you have an idea that you can’t stop dreaming about, this week’s episode is the inspo you need. We chat with Ashley Freeborn, the founder and CEO of the renowned fashion brand Smash + Tess, about all things brand building, entrepreneurship, using fear to fuel your fire, and tapping your network to help get your idea off the ground.

You’ve probably seen people rocking Ashley’s rompers on instagram, or heard about her epic collabs with Jillian Harris, Sarah Landry of The Birds Papaya and Hilary Duff, just to name a few. Her brand started the #romperrevolution but here’s why we honed in on Smash + Tess for today’s episode: Ashley isn’t a serial entrepreneur or longtime business or fashion mogul, she just had an idea to fill a gap in the market, and made her dream a huge reality. What she created is so much more than a clothing company, it’s a community, a lifestyle and an inclusive brand that empowers women to live their best lives.


This episode is brought to you by Dove


Roxy Earle

Vaxxed girl summer is in full swing, and there’s so much good energy and hope again! But summer can also be a very triggering time for a lot of people when it comes to body image and insecurities. We polled you guys on Instagram about how you’re feeling in terms of confidence and self-acceptance, and we learned that we’re definitely not alone in this feeling. 76% of you said that summer triggers your insecurities, while 77% of you are feeling anxious about re-emerging from lockdowns with all the physical and mental changes we’ve undergone. 91% of you said that you struggle with negative self-talk, and we feel you...we can all be our own worst critics and bullies.

That’s why we called in body positivity activist and the Queen of confidence, Roxy Earle. We’re on a mission to help everyone (including ourselves) positively develop the single most important relationship we’ll ever have — our relationship with ourselves. And that requires unconditional self-love, compassion, gratitude and some helpful tools to get us out of negative spirals when we’re struggling with our self-esteem or body image. 

Roxy is a former marketing professional turned model, entrepreneur, body positivity activist and a star on Real Housewives of Toronto. She started the #MySizeRox movement, which advocates that confidence comes in all shapes and sizes. She’s worked with brands like Knix, H&M, Le Chateau and Joe Fresh to bring more inclusive sizing and styles to their stores, and is launching the Ana App, which is a tool to increase positivity & confidence while also optimizing your health. 

Tune in as we chat about:

  • Gill’s mindset shift for dealing with negative spirals, finding pride and respect in herself, and abandoning clothing sizes

  • Cailyn’s newfound outlook on self-love & body image as a soon-to-be mom

  • The moment that inspired Roxy to start the #MySizeRoxs movement

  • How confidence became her secret sauce and how to cultivate it (hint: it’s not genetic, it’s accountability!)

  • Roxy’s tips for practicing positive self-talk and self-love daily

  • Why Roxy is advocating for inclusivity and representation in the fashion industry

  • How a gratitude practice can help you combat insecurities and change your life

  • Why filters and body contouring apps are unattainable, exhausting and quite honestly...boring!

  • The mindset shift to have a healthier relationship with your body

  • The importance of practicing and modelling self-love as a parent

  • The #1 tip for looking and feeling your best in photos

We hope this episode inspires you to wear the damn shorts this summer and to start loving yourself unconditionally. You deserve it. And if you need any support on your self-love journey, we’re here for you.


Follow Roxy:

@luxuriousroxy

Get the Ana App (coming soon): 

instagram.com/theanaapp/


This episode is brought to you by Dove. Visit teachmehowtoadult.ca/dove for details on how to try a free sample of their Deep Moisture Hand Sanitizer that we can’t stop raving about!


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


Related Episodes:

Read More