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.

Olivia Alboher has one rule: don’t date other dancers. But what begins as a boundary turns into a conversation about heartbreak, reputation, and the silent ways we try to keep our lives from colliding. A tender episode about work, love, and the blurry line between them.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Olivia: https://bit.ly/40TlsfiShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSLTIMESTAMPS00:00 – The chaos of the perfect date 00:24 – Meet Olivia Alboher: dancer, model, and Broadway alum 02:45 – Behind the scenes of So You Think You Can Dance 03:50 – Why Olivia won’t date other dancers 05:30 – Crushes, auditions, and the dance world drama 07:00 – Fame, dating apps, and why men won’t text first 09:00 – Patterns in love: no type, just a vibe 11:00 – Humor, charisma, and red flags that matter 14:00 – When people pretend to have it all figured out 16:00 – Ideal dates, invisible ink, and Petco fish rescues 20:55 – East Coast vs. West Coast dating 24:30 – Dating post-breakup and Olivia’s take on Raya 26:00 – Should your partner be a superfan or stay low-key? 27:00 – Red flag / green flag game: DJs, dancers & soft launches 35:50 – Final thoughts & wrap-up

Luvstruck shares how she went from grinding Fortnite 14 hours a day to finding balance, purpose, and a love for the outside world. Caitlin and Luvstruck reflect on growing up online, career burnout, and the difference between gaming with someone—and really connecting.Follow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Luvstruck: https://bit.ly/43IQAAdShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSLTIMESTAMPS00:00 – Intro & Gaming Origins03:00 – From Cheerleading to Fortnite06:00 – Streaming, Burnout & Finding Balance10:00 – Birthday Streams & Online Community13:00 – Roblox, Red Flags & Ideal Partners18:00 – Dating, DMs & Confidence23:00 – Heartbreak Hotline Advice30:00 – Red Flag / Green Flag Game38:00 – Final Thoughts & Where to Find Luvstruck

Frenchi thought she was in love. They lived together, shared a life, and talked about forever—until a single conversation revealed a reality she never saw coming. In this episode, she opens up about finding out the truth while her partner was in a coma, what it means to reclaim your story when the world mislabels you, and how she found clarity on the other side of chaos.TIMESTAMPS00:00 – Welcome to Heartbreak Hotel01:00 – DJing for Women, Vibes, and Energy08:00 – The Reality of LA Nightlife14:00 – Balancing Frenchie and Ray Kitara21:00 – Sex Work, Confidence, and Misconceptions30:00 – Dating, Insecurity & Emotional Intelligence41:00 – Spy Missions, Confetti Cannons & Chaos46:00 – The Coma, the Cheating, and the Plot Twist57:00 – Healing, Moving On, and Finding Yourself Again1:07:00 – Red Flag / Green Flag1:15:00 – Final Reflections & Where to Find FrenchieFollow the podcast: http://bit.ly/4jXECZsFollow Caitlin: https://bit.ly/4gHGVNlFollow Frenchi: https://bit.ly/3Zux9IBShot and Edited by Pixl Saucehttps://bit.ly/3QiSTSL

Why lie? Ariel Bray reflects on her journey in LA, the differences between dating men & women, and the consequences of the truth coming out too late.👇 TIMESTAMPS0:00 – The pressure to have it all figured out0:45 – Welcome to Heartbreak Hotel1:09 – Moving to LA & surviving the chaos1:38 – Becoming a DJ + TikTok series2:05 – Exploring sexuality and feminine/masc style4:52 – Coming out in high school & finding community6:42 – Mark Wahlberg’s movie about her old school?!8:04 – Style struggles, queer presentation, and shopping for “two people”8:48 – Dating men vs. women: what’s different10:24 – Dating dynamics, emotional needs, and protection13:42 – Who are the better liars: men or women?15:40 – Dating a frat bro (and the booger wall saga)21:12 – The best friend plot twist and Facebook baby bombshell27:00 – The infamous church story35:00 – When he ghosts you… for church with his ex41:13 – Red Flag / Green Flag rapid fire47:54 – Where to follow Ariel Bray

Sure, the men are trash. But Caitlin and Sydney have snacks, inside jokes, and a mutually agreed-upon crash out schedule. This episode is for the girlies choosing chaos together — because if you’re going to lose your mind, might as well do it with your best friend.

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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.

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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?

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