Pretty Wrong

Andrea Levoff
  • 5.0 (7)
  • COMEDY INTERVIEWS

A podcast where two friends settle your drama, one petty case at a time. 

  1. 21H AGO

    Shark Week

    In this episode of Pretty Wrong, Demi and Andrea catch up after the holidays and jump right into a couple of relationship moments that sparked bigger conversations. Demi shares a vacation fight that started when her boyfriend insisted on swimming far out into the ocean despite warnings — and how what felt adventurous to him triggered real anxiety for her. We talk about nervous systems, feeling emotionally considered, and how couples handle fear differently. We also break down a listener question about traveling with another couple when one partner is over the friendship and the other feels obligated to keep it going. Boundaries, loyalty, and knowing when it’s okay to opt out all come up. A relaxed, honest episode about communication, anxiety, and navigating relationship gray areas — where no one is fully right or fully wrong.

    31 min

  2. JAN 2

    Letting Go, Holding On, and Doing the Work — ft. Jacq Gould

    This week on Pretty Wrong, we’re joined by our friend Jacq Gould — founder of “Your Inner Babe” — for a real conversation about the relationships that quietly change as we grow. We talk about the friendships that fade without a big blowup, the weird grief of outgrowing people you still love, and how hard it can be to move forward without making anyone the villain. We also get honest about marriage — the work, the repair, the seasons where connection takes effort. Jacq brings her perspective from helping women reconnect with themselves, but this episode isn’t about self-help — it’s about the messy, human side of loving people over time. We get into: • friendship “expiration dates” • when to fight for a relationship vs. when to let it go • why change feels like loss (even when it’s right) • what people mean when they say “marriage is work” • choosing growth without guilt If you’ve ever wondered whether you’ve outgrown someone — this one’s for you.

    40 min

  3. 12/26/2025

    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 plant instead. If you’ve ever felt like you were dating someone who secretly wants to be the princess, this one will hit.

    39 min

  4. 12/19/2025

    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 culture, intuition, and growth, this conversation offers a grounded, honest take on mental health without the buzzwords. If you’ve ever wondered whether you’re doing healing “right,” felt stuck comparing your life to others online, or questioned what desire is really trying to tell you, this episode is for you

    40 min

  5. 12/12/2025

    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.

    36 min

  6. 12/05/2025

    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.

    34 min

  7. 11/28/2025

    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.

    42 min

  8. 11/21/2025

    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

    37 min
See All (17)

5
out of 5
7 Ratings

About

A podcast where two friends settle your drama, one petty case at a time. 

Information

  • Creator
    Andrea Levoff
  • Years Active
    2025 - 2026
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © 2026 Pretty Wrong
  • Show Website
    Pretty Wrong

You Might Also Like