Episode 115: When God Doesn’t Follow Your Timeline
What do you do when God’s timeline looks nothing like the one you planned? We’re talking surrender, waiting seasons, unanswered prayers, and learning to trust God when you can’t see what He’s doing. If you’re struggling to release control and trust the process, this episode is for you.
Episode 114: Dating While Still Healing
Do you have to be fully healed before you start dating again? This week, we’re talking about getting back out there after heartbreak, breaking old dating patterns, holding your standards, navigating new crushes and anxiety, and shifting from wanting to be chosen to deciding who you actually want to choose. Because healing and dating don’t always happen one after the other—sometimes, they happen at the same time.
Episode 113: Life Lately
It’s time for a herspective catch-up! Jillian and Drey are talking life lately—from Greece, books, wedding planning, dating, gym anxiety, and sourdough to the Four Burner Theory and why balancing everything at once feels nearly impossible. Plus, Jillian shares a special tribute to her dad for his 70th birthday.
Episode 112: Say The Thing
Sometimes healing begins by finally naming what happened. In this episode, Jillian and Andrea unpack emotional abuse, betrayal trauma, shame, self-blame, and the difficult truths they had to face in order to move forward. They explore the healing power of therapy, trusted relationships, writing, creativity, and faith—and why “saying the thing” doesn’t always mean telling the world. Sometimes, it simply means finally telling yourself the truth.
Episode 111: How To Be A Friend
What does it actually mean to be a good friend when life gets hard? In Episode 111, Jillian and Andrea talk about the people who showed up during their hardest seasons, why “let me know if you need anything” isn’t always enough, and the small gestures that can make someone feel truly seen. From 2 a.m. phone calls and comeback playlists to calling your friends on their BS, knowing when to listen instead of problem-solve, and learning to be supportable yourself, this episode is a reminder that real friendship isn’t just about saying you’re there—it’s about showing up.
Episode 110: Bad Advice
Some advice sounds good—until you actually think about it.
This week Jillian and Andrea unpack the “bad advice” we hear about breakups, revenge, relationships, following your heart, chasing your dreams, and moving forward. From getting “under someone new” to revenge bodies and cutting off access, they’re asking one important question: whose advice actually deserves a place in your life?
Because advice is just a suggestion. You’re allowed to say, “Thanks, but no thanks.”
Episode 109: How To Know When It’s Time To Go (Part Two)
In Part Two of HTKWITTG, Jillian and Andrea explore how emotional abuse, self-abandonment, and manipulation can make it difficult to recognize when it's time to leave a relationship. Through personal stories and practical reflection, they discuss trusting your intuition, setting healthy boundaries, and finding the courage to choose yourself.
Episode 108: How To Know When It’s Time to Go (Part One)
How do you know when a relationship needs more work—and when it’s time to walk away? Jillian and Andrea unpack the complicated space between staying and leaving, sharing their own experiences with broken boundaries, unhealthy conflict, divorce, communication, and the pressure of letting go of the future you thought you were building. It’s an honest conversation about recognizing patterns, trusting yourself, and knowing when continuing to pour into something may be costing you more than walking away.
Episode 107: Why We Stay Too Long
Why do we stay in relationships, careers, and seasons of life that we know are no longer serving us? Jillian and Andrea explore the hidden beliefs that keep us stuck—from fear and shame to loyalty, identity, and the sunk cost fallacy—and share how choosing peace often begins with letting go.
Episode 106: Our Current Chapter
This week we're sharing our current chapter—dating, careers, healing, friendships, fantasy books, and everything in between. Come hang out with us.
Episode 105: Your Life Just Blew Up, Now What?
What do you do when life changes without your permission? In this heartfelt episode, Andrea and Jillian share personal stories of divorce, betrayal, unexpected illness, and other involuntary transitions while exploring how faith, community, and hope can help you rebuild when everything feels like it's fallen apart.
Episode 104: The Space In Between
You've done the work—now what? Jillian and Andrea unpack the challenges of life's waiting seasons, discussing healing, faith, discernment, and the quiet growth that happens before the next chapter begins.
Episode 103: Loneliness, The Weight of Begin Alone (Part 2)
In part two of their conversation on loneliness, Jillian and Andrea unpack the hidden weight of being alone—exploring grief, toxic cycles, self-discovery, and the courage it takes to heal without rushing the process.
Episode 102: Loneliness, The Weight of Begin Alone (Part 1)
In this honest and vulnerable conversation, Jillian and Andrea share the seasons of life that forced them to confront loneliness head-on.
Episode 101: The 2 AM Friend
In this deeply personal conversation, we're sharing the story behind the podcast, the friendship that started it all, and the difficult seasons that ultimately brought us here.