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Pretty Wrong
Andrea Levoff
15 episodes
3 days ago
This week on Pretty Wrong, we’re breaking down the “princess man” — the guy who wants the attention, effort, praise, and emotional support, while somehow still giving the bare minimum. We talk about how dating apps and self-care culture helped create him, the difference between genuine needs and entitlement, what healthy reciprocity actually looks like, and why so many women end up over-functioning without realizing it. We even explore whether Andrea should start dating at a manufacturing pla...
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Comedy Interviews
Comedy
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This week on Pretty Wrong, we’re breaking down the “princess man” — the guy who wants the attention, effort, praise, and emotional support, while somehow still giving the bare minimum. We talk about how dating apps and self-care culture helped create him, the difference between genuine needs and entitlement, what healthy reciprocity actually looks like, and why so many women end up over-functioning without realizing it. We even explore whether Andrea should start dating at a manufacturing pla...
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Comedy Interviews
Comedy
Episodes (15/15)
Pretty Wrong
The Rise of The Princess Man
This week on Pretty Wrong, we’re breaking down the “princess man” — the guy who wants the attention, effort, praise, and emotional support, while somehow still giving the bare minimum. We talk about how dating apps and self-care culture helped create him, the difference between genuine needs and entitlement, what healthy reciprocity actually looks like, and why so many women end up over-functioning without realizing it. We even explore whether Andrea should start dating at a manufacturing pla...
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3 days ago
39 minutes

Pretty Wrong
The Internet is Not Your Therapist
In this episode of Pretty Wrong, we dive into therapy, comparison, and the quiet ways social media shapes how we see ourselves. We talk about why comparison feels especially intense during the holidays, how boundaries actually work in real life, and why comparing your inner world to someone else’s highlight reel is never accurate. We explore how desire isn’t proof of lack, but information. A signal from your future self about what’s possible. From parenting and boundaries with kids to healing...
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1 week ago
39 minutes

Pretty Wrong
The Betrayal Tour
After uncovering some truly chaotic double-dating behavior, the girls map out the only logical response: Betrayal Tour. Demi and Andrea break down: - Why grand gestures aren’t apologies - The “Giant B*tch” dating philosophy - First-date anxiety hacks - Tattoo red flags & more Buckle up because this week's episode might just change your dating life.
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2 weeks ago
35 minutes

Pretty Wrong
Surprises, Shenanigans, and a Dog Named Honey
A few weeks back, Demi was in full-blown "Girlfriend Purgatory", and this week? A surprise ring-shopping trip flipped the script. The girls unpack the emotional whiplash of going from “Are we doing this?” to “Oh wow… we’re doing this.” Also in this episode, Andrea and Demi discuss fake authenticity to holiday gift-giving panic.
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3 weeks ago
33 minutes

Pretty Wrong
Look Good, Feel Good, Have Fun
Lauren Elizabeth is here and it is pure chaos in the best way. We talk about her upcoming wedding, why she considered letting ChatGPT help write her vows, and whether blocking someone is a reasonable coping mechanism or a red flag wrapped in self-care. Plus: motherhood, expectations, and the art of being a little unhinged but still lovable. If you want honesty + comedy + a touch of delusion, this one is for you.
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1 month ago
42 minutes

Pretty Wrong
Girlfriend Purgatory
This week, Andrea and Demi spiral (productively) through their manic era — kicking off with the start of Andrea’s Betrayal Tour. We get into why post-Halloween contact removal is a spiritual experience, debate whether you should ever share your trainer with your partner, and weigh in on a listener who throws away dishes when her spouse won’t wash them. It’s the perfect blend of unhinged honesty, relational chaos, and Pretty Wrong wisdom — welcome back to the group chat
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1 month ago
36 minutes

Pretty Wrong
“Real Connection > Swiping: Why The Feels Works
Allie Hoffman from The Feels joins us to break down why dating apps didn’t just change how we meet — they changed how we behave. No more friend intros. No more accountability. No more “be decent because we run in the same circles.” Now it’s swiping, ghosting, vanishing, repeat. We get into: • Why nobody knows how to approach someone in real life anymore • How apps rewired our sense of connection • What we actually crave (spoiler: it’s not more options) • And why The Feels is bringing dating b...
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1 month ago
37 minutes

Pretty Wrong
Looking “Chopped” being held by the masculine container, and the last minute friend.
In this episode, we talk about those photos — the ones where you look back and think, “Wait… why do I look chopped?” and how much of our identity gets tangled up in being seen. We get into the difference between doing vs receiving — masculine energy that takes action versus feminine energy that allows, rests, and opens. And how sometimes the deepest growth is learning to be loved without performing for it. And of course, we celebrate one of life’s greatest gifts:a friend who lets you cancel p...
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1 month ago
35 minutes

Pretty Wrong
Dress for the Life You Want (and the Queen You Already Are)
This week, Andrea and Demi sit down with stylist and self-love advocate Tali, who believes that every woman is a queen — and that how we dress can reflect (and reshape) how we see ourselves. They talk about: 👑 Dressing for the life you want, not the one you’re stuck in 💫 The connection between confidence and clothing 👜 Why your bag might just be your crown ❤️ How fashion helped Tali through some of the hardest seasons of her life It’s an episode about self-worth, reinvention, and the quiet po...
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1 month ago
40 minutes

Pretty Wrong
The Modern Woman’s Starter Pack
This week, Andrea and Demi unpack the unofficial starter pack of the modern woman — from crying on social media with your tripod out, to the cult of group fitness classes, to one listener’s marriage mystery: why does she leave water bottles everywhere? It’s a mix of chaos, culture, and comedy as we break down what it means to be “that girl” in 2025 — emotionally unhinged, spiritually self-aware, and probably late to Pilates.
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2 months ago
35 minutes

Pretty Wrong
Fired, but make it Transformational
This week, Demi opens up about getting fired — and why it might’ve been the best thing that ever happened to her. We talk about parenting meltdowns, unexpected blessings, and yes… the time she peed her pants at a Hanson concert.
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2 months ago
41 minutes

Pretty Wrong
Weight Loss Myths That Won't Die ( and What Actually Works)
Everyone’s got a theory about weight loss — eat less, move more, skip breakfast, do fasted cardio, cut carbs, the list goes on. In this episode, Andrea sits down with her trainer Joel, who’s here to break down the science behind what actually works (and what’s total BS). From metabolism myths to the truth about GLP 1 — this conversation cuts through the noise with research, humor, and a little tough love. Whether you’re in your fitness girl era or just trying to understand your body better, t...
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2 months ago
55 minutes

Pretty Wrong
Weddings, Friendships & Bachelorettes in Chainmail
In this episode, we dive into the messy, beautiful shifts of female friendship — from losing mom friends as life stages change, to the bittersweet reality of growing apart. We talk about what it’s like to attend a wedding after divorce (spoiler: you see everything differently) and, of course, the unexpected drama of a Medieval Times bachelorette party. It’s about endings, beginnings, and finding your place when the cast of characters around you starts to change.
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2 months ago
45 minutes

Pretty Wrong
No Makeup, New Beginnings & Pretty Wrong’s Origin Story
Welcome to the very first episode of Pretty Wrong! In this debut, Andrea shares the raw and hilarious journey of giving up makeup for over a year — what started as a spiritual experiment quickly turned into a crash course in identity, confidence, and showing up in the world as your unfiltered self. You’ll also hear the birth story of Pretty Wrong — how a DM exchange with Demi (over heartbreak, hair appointments, and way too many voice notes) turned into the podcast we just had to create. From...
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3 months ago
42 minutes

Pretty Wrong
Pretty Wrong Trailer
4 months ago

Pretty Wrong
This week on Pretty Wrong, we’re breaking down the “princess man” — the guy who wants the attention, effort, praise, and emotional support, while somehow still giving the bare minimum. We talk about how dating apps and self-care culture helped create him, the difference between genuine needs and entitlement, what healthy reciprocity actually looks like, and why so many women end up over-functioning without realizing it. We even explore whether Andrea should start dating at a manufacturing pla...