This Is What Happens When You Break a Songwriter’s Heart | HH #14 | Lily Brooks O'Briant

Being nice won’t save you—it’ll bore her to death. On this week’s Heartbreak Hotel, professional texting Coach Grand Cam shares why playing it safe never works, what “respectfully unhinged” looks like, and how to turn off the polite version of you that’s getting ghosted on the regular.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Coach Grand Cam: https://bit.ly/42qGweqShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

Can a breakup text turn into a viral hit? It did for Lily Brooks O’Briant. She joins Caitlin at Heartbreak Hotel to talk songwriting, dating red flags, and why sometimes you just have to name names.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Lily: https://bit.ly/3YmSKCjShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

Men in their 30s are still posting thirst traps, frat boys have the emotional depth of a puddle, and someone just offered Sami Brielle money to tickle her feet. The internet is a lawless place, and we’re here to investigate. Join us as we roast bad dating habits, questionable relationship red flags, and the absolute worst DM Sami has ever received. Plus: The art of fake confidence, surviving high school bullies, and why no one needs to last an hour in bed. Seriously.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Sami: https://bit.ly/4bEKjYrShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

One minute you’re dating, the next they’re a full-blown influencer. How did we get here, and is it too late to delete their career?Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Tim: https://bit.ly/3Db4XCQShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

Nothing says “I’m over it” like spending an entire savings account on a girl just to be told the Lord prefers her single. Join us for tequila shots, trauma bonding, and the exact guide to restaurants that guarantee ghosting.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Dylan: https://bit.ly/3D4RjkuShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

"Russian dance moves = instant rizz?" Dillon thinks so. Also, should you ever check your partner’s phone? Probably not, but let’s argue about it anyway.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Dillon: https://bit.ly/40ZkM7wShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

Check into Heartbreak Hotel with Andrés Zannelli & Caitlin Erin O'Neill for a New Year's Eve filled with shots, stories, and bank heists. Follow Andrés on Insta @andreszannelli

Actress Mercedes Blanche joins Caitlin Erin O'Neill on Heartbreak Hotel to drop some insane stories about past relationships, and everything she's learned from those experiences. Mercedes' Instagram: https://www.instagram.com/mercedes.blanche/ Caitlin's Instagram: https://www.instagram.com/caitlinerinoneill Shot and Edited by Pixl Sauce https://www.pixlsauce.com

Joining Caitlin Erin O'Neill this week for a very special episode of Heartbreak Hotel: meet our producer, Mitchell Kennard Francis and his fiancée, actress Taylor Winks.

19 year old Actress, Model, and Streamer Makenzie Raine checks into Heartbreak Hotel with Caitlin Erin O'Neill for Episode 6 to share her experiences with these LA men, and give advice to Heartbreak Hotel viewers with questions about their dating lives.