Stepmom Side Chats

In this episode, Alyssa and Becca sit down to unpack what this holiday really feels like as stepmoms, especially when you’re doing all the “mom things” but don’t always get the recognition that comes with it.
They reflect on where they started, navigating Mother’s Day as childless stepmoms, and how their experiences have evolved over time. From awkward first holidays to now balancing life as both stepmoms and biological moms, Alyssa and Becca share the honest, unfiltered reality of what this day brings up.
They get into the tough questions, what hurts more, no acknowledgment or forced acknowledgment? What role should partners actually play? And how do kids experience this day when they’re caught between two homes?
Along the way, Alyssa and Becca talk about expectations, resentment, growth, and why creating your own version of Mother’s Day might be the key to getting through it.
If you’ve ever felt invisible, conflicted, or unsure where you fit on Mother’s Day, this conversation will make you feel seen.

✨ Big Ass Candles | www.bigassluxuries.com and use the code STEPMOM for a discount
✨ Episode sponsor | ⁠www.cozyearth.com⁠ and use code STEPMOM
✨ Pateron private stepmom membership: ⁠⁠https://patreon.com/Stepmomsidechats⁠⁠
✨ Follow us on Instagram for more stepmom content and to stay connected for future episodes ⁠⁠@stepmomsidechats⁠⁠
✨ Leave us a review if this episode resonated with you, this helps us reach more stepmoms.

In this episode of Alyssa & Becca, we sit down with Ashton Whitmoyer-Ober, an Enneagram coach and speaker, to talk about how understanding your Enneagram type can help you navigate stepmom life with more self-awareness, clarity, and compassion.
We get into how different Enneagram types respond to conflict, triggers, boundaries, people-pleasing, resentment, and relationship dynamics, especially inside blended families. We also talk about why stepmom life can feel so emotionally layered, how your core motivations shape the way you react, and what it can look like to better understand both yourself and the people around you.
Whether you are the stepmom who overthinks everything, takes things to heart, avoids conflict, or feels like you always have to prove yourself, this conversation offers insight into why you may respond the way you do and how that awareness can help you move through blended family dynamics with more intention.
We also answer a listener question and share practical takeaways for stepmoms who want to better understand their triggers, communication patterns, and emotional responses.

Connect with Ashton:
Instagram: @enneagramashton Website:https://www.enneagramashton.com/

✨ Big Ass Candles | www.bigassluxuries.com and use the code STEPMOM for a discount
✨ Episode sponsor | www.cozyearth.com and use code STEPMOM
✨ Pateron private stepmom membership: ⁠https://patreon.com/Stepmomsidechats⁠
✨ Follow us on Instagram for more stepmom content and to stay connected for future episodes ⁠@stepmomsidechats⁠
✨ Leave us a review if this episode resonated with you, this helps us reach more stepmoms.

Season 2 is here and we’re starting with a conversation so many stepmoms know by heart. In this first episode, Alyssa & Becca talk about the exact moment they realized stepmom life was not what they thought they signed up for. From overfunctioning, unrealistic expectations, and feeling invisible in your own home, to the emotional labor, criticism, and identity shifts no one prepares you for, we’re getting honest about the parts of stepmom life that hit the hardest.
We’re also sharing what we wish we would’ve known earlier, the boundaries we wish we’d set sooner, and the biggest lessons we’ve learned along the way. If you’ve ever thought, “Wait… this is not what I expected,” this episode is for you.

✨ Big Ass Candles | www.bigassluxuries.com and use the code STEPMOM for a discount
✨ Episode sponsor | ⁠www.cozyearth.com⁠ and use code STEPMOMBOGO
✨ Pateron private stepmom membership: ⁠⁠https://patreon.com/Stepmomsidechats⁠⁠
✨ Follow us on Instagram for more stepmom content and to stay connected for future episodes ⁠⁠@stepmomsidechats⁠⁠
✨ Leave us a review if this episode resonated with you, this helps us reach more stepmoms.

It’s our season finale, and we are showing up caffeinated, chaotic, and completely unfiltered. Alyssa and Becca playing “Would You Rather: Stepmom Edition”, from sports practices vs. parent-teacher conferences to stepping on Legos vs. reading a six-paragraph text from the ex. They also tackle listener-submitted questions about dating a partner with a toddler, long-distance stepkids, and what it’s like when you have less than 50/50 time.
Plus, they are sharing a little life update on transition days, stepmom triggers, and why “let it go” is way easier said than done.
They discuss taking a short break before Season 2, but how they still be hanging out inside the Stepmom Side Chats membership with lives, Q&As, and support you don’t have to explain.

✨ Pateron private stepmom communities: https://patreon.com/Stepmomsidechats
✨ Follow us on Instagram for more stepmom content and to stay connected for future episodes @stepmomsidechats
✨ Big Ass Candles | https://bigassluxuries.com and use the code STEPMOM for a discount
✨ Leave us a review if this episode resonated with you, this helps us reach more stepmoms.

This week on Stepmom Side Chats, we sit down with co-parent coach Jay Skibbens for a conversation that goes deep, like identity-shifting, nervous-system-resetting deep.
Jay shares his powerful personal story of discovering that the children he had been raising weren’t biologically his and how that experience reshaped his understanding of resentment, emotional regulation, and what co-parenting really requires. From carrying years of anger to learning how to “cook his emotions first,” Jay breaks down why so many blended family conflicts aren’t actually about the kids: they’re about unprocessed triggers.
This episode challenges the scripts we’ve all been handed about co-parenting. It’s not about winning. It’s not about controlling the other house. It’s about learning how to stay grounded when the triggers hit, because in blended families, they will.
If you’ve ever felt dysregulated on transition day, resentful about schedules, frustrated with your spouse, or triggered by the other home, this conversation is for you.
You can find Jay on instagram at @jayskibbens or through his membership, The Grounded Coparent University.
The Grounded Coparent University is a private membership teaching regulated co-parenting through structure, tools, and repeatable growth. $49/month. Doors open March 23rd so use this link to get on the waitlist to save your spot: https://jay-skibbens.mykajabi.com/opt-in-9348c019-f9c1-4b91-8ab2-f6ad95ca18ab

✨ Pateron private stepmom communities: https://patreon.com/Stepmomsidechats
✨ Follow us on Instagram for more stepmom content and to stay connected for future episodes @stepmomsidechats
✨ Big Ass Candles | https://bigassluxuries.com and use the code STEPMOM for a discount
✨ Leave us a review if this episode resonated with you, this helps us reach more stepmoms.