Pretty and Painful

Bailey Lewis

5.0 (2)
SOCIETY & CULTURE
UPDATED WEEKLY

Pretty and Painful is a podcast about grief, grace, and showing up anyway. Hosted by B, this is a space for honest conversations about loss, healing, and finding beauty in the middle of the hard things — with heart, humor, and a little sass. Real life, real feelings, and the reminder that healing doesn’t have to be quiet or perfect.

1D AGO

Episode 27: I Saw you today

Episode 27 — “i saw you today” Sometimes grief doesn’t crash through the front door. Sometimes it pulls up beside you at a gas pump under a red sunset sky and steals the air right out of your lungs. Today I saw a stranger… but for a second, my heart swore it was you. This episode is about the weirdness of grief — the double takes, the familiar faces, the moments that feel like warm hugs and heartbreak all at once. The kind of grief that sneaks up on you when you thought you were finally okay. We’re talking about longing, memories, signs, God’s timing, and learning how to carry love for people who are no longer standing beside us physically… but somehow still show up everywhere. Because sometimes healing looks like laughing one day… and crying at strangers the next. Pretty & Painful Podcast — where grief and joy still sit at the same table. 🩷

13 min
2D AGO

Episode 26: Why are they so nice?

I found myself asking a question lately that honestly felt a little embarrassing to say out loud: “Why are they so nice to me?” Not fake nice. Not performative nice. Not nice with hidden intentions attached to it. I mean genuine kindness. Patience. Gentleness. The kind of love that doesn’t keep score. And maybe that question says more about what I’ve survived than anything else. In Episode 26 of Pretty & Painful, we’re talking about what happens when you’ve spent so long living around criticism, tension, conditional love, and survival mode… that healthy love almost feels uncomfortable. Because when you’re used to walking on eggshells, kindness can feel confusing. This episode is about healing through people who love differently. People who choose softness. People who reflect God without needing a stage to do it. Maybe real faith looks less like perfection and more like how we treat hurting people. And maybe for the first time in a long time… I’m learning that love was never supposed to hurt this much to be real. Episode 26 — Why Are They So Nice? 💗

17 min
6D AGO

Episode 25 : Grace for the girl i used to be

Episode 25 of Pretty & Painful is for the girl who still cringes at old Facebook memories, old choices, old relationships, old coping mechanisms… and forgets she was surviving the best way she knew how. This episode is about grace. Not just the kind God gives us — but the kind we struggle to give ourselves. Bailey opens up about grieving old versions of herself, carrying shame for seasons she barely survived, battling grief, depression, pain, and feeling far from God… while learning that healing doesn’t mean pretending the past never happened. It means realizing the girl you used to be still deserves compassion too. Because maybe she wasn’t weak. Maybe she was exhausted. Maybe she was drowning. Maybe she was doing everything she could just to stay alive. This episode is raw, reflective, faith-filled, and honest — for anyone trying to stop hating who they had to become in order to survive. “God makes all things new… and that includes me.” Pretty & Painful Podcast Where grief and joy sit at the same table.

17 min
MAY 13

Episode 24: Blurred Vision, Clear Grace

Hindsight is 20/20… but sometimes our vision isn’t. In Episode 24 of Pretty & Painful, Bailey dives into blurry seasons — the moments we ignored red flags, drifted from ourselves, questioned God’s timing, or got so lost in survival mode that we stopped seeing clearly. This episode is about slow blooming, spiritual burnout, hindsight, grace, and learning that healing doesn’t always happen all at once. Sometimes God meets us quietly… in the stillness, in the flowers blooming slowly, and in the moments we finally stop running long enough to listen. If you’ve ever felt spiritually squinty, emotionally exhausted, or stuck between grief and growth — pull up a chair. Because even with blurry vision… grace still sees us clearly. 🌸 Faith. Healing. Hindsight. Grace

22 min
MAY 12

Episode 23: Borrowing Happiness

Borrowing joy until you can hold your own again. Maybe grief made your hands too heavy to carry happiness for a while. Maybe watching everyone else heal, grow, fall in love, laugh, and live felt easier than figuring out how to do it yourself. But somewhere along the way… their joy reminded me mine still existed too. And babes? I spent so long wondering if I even deserved a seat at the table… until I realized: I am the table. ✨ 🎙️ Pretty & Painful Podcast Where grief and joy sit at the same table.

11 min
MAY 9

Episode 22 : Hauled not Healed

Some fires don’t happen all at once. Sometimes they spark slowly. A bad season. A hard goodbye. A little grief. A little healing. A little chaos wrapped up in confidence and sarcasm. In this episode of Pretty & Painful, we’re talking about dumpster fire moments, emotional cleanup jobs, the people God sends into your life at the right time, and learning that being “hauled, not healed” doesn’t mean you’re broken beyond repair. Because maybe healing isn’t always soft. Maybe sometimes it looks like sparks flying, smoke everywhere, and still finding a way to laugh through it. ✨ Hauled, Not Healed: Sparks & Sass 🎙 Pretty & Painful Podcast “Where grief and joy sit at the same table.”

14 min
MAY 6

Episode 21: The one someone buys

Episode 21 — the one someone buys I thought he was going to give me specs & storage… but turns out it was never really about the iPad. This episode is about what happens when you realize being “chosen” and being truly valued are two very different things. The gifts, the gestures, the convenience of having someone around — and the quiet ache of wondering if they actually see you underneath it all. We’re talking relationships, emotional availability, soft life illusions, and the difference between being loved loudly… and being loved well. Because babes, it’s more than an iPad. It’s about feeling worthy without having to earn it. ✨ Pretty & Painful — where grief, growth & gloss sit at the same table.

12 min
MAY 5

Episode 20: I'm a-lot & i'm not sorry

“Too much… or just finally honest?” This episode is for the ones who have been called too much. Too loud. Too emotional. Too honest. In this raw, unfiltered episode of Pretty & Painful, Bailey opens up about grief, healing out loud, and the reality of being misunderstood in a world that prefers things quiet and palatable. From accusations of “doing it for attention” to choosing what parts of her story stay private, this is a conversation about identity, growth, and refusing to shrink for anyone. Because not all healing is quiet. And not everyone is meant to understand you. ✨ If you came here for quiet… you picked the wrong table.

14 min

5

out of 5

2 Ratings

Pretty and Painful is a podcast about grief, grace, and showing up anyway. Hosted by B, this is a space for honest conversations about loss, healing, and finding beauty in the middle of the hard things — with heart, humor, and a little sass. Real life, real feelings, and the reminder that healing doesn’t have to be quiet or perfect.

Creator

Bailey Lewis
Years Active

2K
Episodes

31
Rating

Clean
Copyright

© Bailey Lewis
Show Website

Pretty and Painful