Heartbreak Hotel

Caitlin O'Neill
  • 4.1 (11)
  • RELATIONSHIPS
  • UPDATED WEEKLY

Modern love. Messy stories. Real advice. Check in every Wednesday with Caitlin Erin O’Neill and a new guest. Heartbreak Hotel: Enjoy your stay.

  1. JAN 7

    I Thought America Idol Would End My Career | Sophie Powers

    Sophie Powers checks into Heartbreak Hotel to talk about her American Idol moment, dating apps, masculinity, red flags, and what it really takes to find confidence in the music industry. From testing masculinity on first dates to navigating fame, fashion, and creative identity, Sophie opens up about her career, relationships, and the lessons she’s learned along the way. New episodes of Heartbreak Hotel every week. Enjoy your stayy Listen to Spiderwebs: https://www.youtube.com/watch?v=2DV8vMaS7Wg Follow Sophie: https://www.instagram.com/sophiep0wers/ Follow Caitlin: https://www.instagram.com/caitlinerinoneill/

    34 min

  2. 12/24/2025

    Gentle Parenting Men & Cancelling an LDS Engagement at 21

    What happens when you grow up Mormon… and then become a comedian? In this Heartbreak Hotel episode, Tyler Bender breaks down how her LDS upbringing influenced her relationships, dating choices, and sense of humor - including getting engaged at 21 and calling off the wedding. From gentle parenting boyfriends to navigating modern dating as a funny woman, this episode covers religion, relationships, marriage pressure, and why being “funny” isn’t the same as trying to be funny.

    46 min

  3. 12/17/2025

    How to Cast a Love Spell From a Witch | Mia Magik

    In this episode of Heartbreak Hotel, Cait checks in with author and witch Mia Magik to talk about the most powerful love spell of all: learning how to feel safe within yourself. They unpack dating patterns, inner-child healing, boundaries, masculine and feminine energy, and why the way you talk to yourself shapes the love that you attract. This episode offers grounded, actionable ways to shift your energy, raise your standards, and attract love that actually feels good. Follow Mia: https://www.instagram.com/miamagik/?hl=en Buy Mia's Book: https://miamagik.com/book/ Follow Cait: https://www.instagram.com/caitlinerinoneill/?hl=en

    1h 5m

  4. 11/19/2025

    Eric Wei Interview: Money, Ambition, and Finding Yourself in Your 20s

    Eric Wei joins Cait to unpack how money trauma shapes dating, why ambitious people struggle in relationships, and how to rebuild your identity when you’ve tied it to achievement for too long. This episode covers: • Financial green flags & emotional red flags • Misattribution theory & reframing anxiety as excitement • Scarcity vs. abundance mindset • Healing your relationship with success • How your 20s shape your future confidence One of the most insightful interviews of the season. Follow Eric on Instagram: https://www.instagram.com/erictway Try Karat: https://www.trykarat.com

    1h 23m

  5. 11/12/2025

    Delulu 101 with Ryan Lu

    Can you really manifest your dream partner? Ryan Lu says yes - if you’re delusional enough. This episode explores the magic of manifestation, the dark side of LA, and the emotional cost of chasing your dreams. Check into Heartbreak Hotel this week to hear about love, hustle, heartbreak, and what it means to believe in yourself when no one else does. Ryan's Instagram: https://www.instagram.com/e.mo.tions/ Stream Delulu: https://open.spotify.com/show/5HzcyoaU3FyT4zALc4m1Ob?si=49286322db4d4519 Caitlin's Instagram: https://www.instagram.com/caitlinerinoneill/

    1h 12m

  6. 10/09/2025

    What Psychics, Ghosts, and Dating Apps Have in Common

    The Heartbreak Horror Night Duo reunites for an October special complete with ghost stories, psychic confessions, and dating app red flags. Caitlin Erin O'Neill (me!) and Tim Kennedy talk EMF readers, the haunted doll that made Caitlin scream, and how energy (and bad exes) tend to linger. A little spooky, a little romantic, and very Heartbreak Hotel. Follow Tim : https://www.instagram.com/_timothykennedy/ HBH Shorts: https://www.instagram.com/heartbreakhotelpod

    1h 3m

  7. 10/02/2025

    How To Approach Women Without Being Weird | Heartbreak Hotel

    Welcome back to Heartbreak Hotel, Season 2! Host Caitlin Erin O’Neill (that's me!) welcomes guest Steven Tyler to break down the unwritten rules of dating. This week, we'll cover everything from how to approach women with confidence, to spotting red flags, to the pressures of navigating LA’s unique dating scene. Steven also opens up about heartbreak, moving on after a long-term relationship, and the surprising places he’s found the most beautiful women in the world. As always, thanks for checking in! Steven's Instagram: https://www.instagram.com/thesteventylerr/ Caitlin's Instagram: https://www.instagram.com/caitlinerinoneill/

    1h 3m
  8. How To Get The Girl In One Sentence | Heartbreak Hotel

    09/24/2025

    How To Get The Girl In One Sentence | Heartbreak Hotel

    This week on Heartbreak Hotel, Caitlin Erin O’Neill welcomes guest Steven Tyler to break down the unwritten rules of dating. They cover everything from how to approach women with confidence, to spotting red flags, to the pressures of navigating LA’s influencer-driven dating scene. Steven also opens up about heartbreak, moving on after a long-term relationship, and the surprising places he’s found the most beautiful women in the world.

    1h 3m
See All (35)

Ratings & Reviews

4.1
out of 5
11 Ratings

About

Modern love. Messy stories. Real advice. Check in every Wednesday with Caitlin Erin O’Neill and a new guest. Heartbreak Hotel: Enjoy your stay.

Information

  • Creator
    Caitlin O'Neill
  • Years Active
    2024 - 2026
  • Episodes
    35
  • Rating
    Explicit
  • Copyright
    © Caitlin O'Neill
  • Show Website
    Heartbreak Hotel