It's Ticked Off Tuesday and Jared is complaining with YOU about 👇

• Marriott concierge lounge closed on weekends
• Chicago parking nightmare made her 40 minutes late
• Deep tissue massages with ZERO spa vibes
• Loud comedy crowd ruined the entire show!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

• Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN
• Let Rocket Money help you reach your financial goals faster at http://RocketMoney.com/JTRAIN

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems!👇

• We had a perfect date, and now he’s gone for 10 days, and I’m spiraling! help!
• I’m a 36 year old widow trying to date casually for the first time, and I have no idea what I’m doing
• My little brother is getting my late grandma’s engagement ring, and I’m furious

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

• Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN
• Let Rocket Money help you reach your financial goals faster at http://RocketMoney.com/JTRAIN

Pop Culture Thursday: Jared reads latest celebrity headlines from Page Six and gives his unfiltered takes!

• Bethenny Frankel shoe drama
• Hilary Duff on the cover of Sports Illustrated Swimsuit Issue 2026
• Justin Baldoni and Blake Lively legal drama
• Taylor Swift and Travis Kelce wedding updates
• Mandy Moore Reacts to Ashley Tisdale's Essay
• Gwyneth Paltrow's daughter, Apple, lands major movie role

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

Sign up for Bilt & start earning points on your rent or mortgage payments. Just go to http://JoinBilt.com/JTRAIN

It’s Chit Chat Wednesday with Financial expert Haley Sachs of Mrs. Dow Jones, who wrote a new book, Future Rich Person! The two talk 👇

• money mindset, taxes, and building wealth
• dating and money in relationships
• game: “How Rich Are You?”

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

Sign up for Bilt & start earning points on your rent or mortgage payments. Just go to http://JoinBilt.com/JTRAIN

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇

• Jared's ticked off at TikTok!
• Every business begging for reviews after every single thing you do
• Airline furniture delivery chaos and weird rules that ruin simple fixes!
• Dog owner drama from lost dogs to messy bad pet habits
• Mother’s Day pressure family plans and emotional guilt trips

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

• Get 40% off select Lola Blankets products at http://Lolablankets.com by using code FEATHER at checkout. Experience the world’s #1 blanket with Lola Blankets.
• Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/jtrain #rulapod #ad

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇

• Destination wedding expectations, maid of honor pressure, and resentment
• Group house trip cost split, shared rooms and fairness questions
• My bf kisses me after his dog licks his whole face!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the podcast by supporting our sponsors!

• Get 40% off select Lola Blankets products at http://Lolablankets.com by using code FEATHER at checkout. Experience the world’s #1 blanket with Lola Blankets.
• Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/jtrain #rulapod #ad

Pop Culture Thursday: Jared reads wild celebrity headlines from Page Six and gives his unfiltered takes!

• Kevin Hart roast backlash
• Tony Hinchcliffe's controversial roast jokes
• Nikki Glaser praised for Tom Brady roast
• Vanna White's appearance trolls slammed
• Tiffany Haddish Sports Illustrated Swimsuit cover
• Meghan Markle's $63K necklace controversy
• John McEnroe crashes Linda Perry's concert
• Michael Richards rare public sighting
• Seinfeld and the comedy industry talk

Support the podcast by supporting our sponsors!

Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

For free shipping on your order & 365-day returns go to https://www.Quince.com/jtrain

Comedian Ashley Hesseltine joins Jared for Chit Chat Wednesday to talk marriage, dating, comedy, and her new comedy special Here Comes the Bride. They talk👇

• Getting married at 42
• Dating in LA vs Boston men
• Prenups and modern marriage
• Meeting her husband through DMs
• Relationship dealbreakers
• The play “For Richer or Poorer”

Support the podcast by supporting our sponsors!

Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

For free shipping on your order & 365-day returns go to https://www.Quince.com/jtrain