Dear Chelsea
On this weekly advice show, comedian & author Chelsea Handler answers listener questions with the hilarious edge you know her for. Joined each week by co-host Catherine Law and celebrity guests, Chelsea never shies away from giving her honest opinion on everything from love, sex and weed to family issues or losing a loved one. Every episode takes you on a ride from funny and informative to inspirational and heartbreaking – and back again. Do you need advice from Chelsea? Send us your question at: DearChelseaPodcast@gmail.com
Episodes
Tim Gunn joins Chelsea to talk about taking no prisoners while fencing, his favorite podcast (👀), and why he’s no longer on Project Runway. Then: A girlfriend and her partner have trouble syncing their sex schedules. A fashion pro finds out his paycheck isn’t what it should be. And a caller fighting cancer struggles with how much to give back.
*
Need some advice from Chelsea? Email us at DearCh...
Chelsea and Catherine get an update from a caller who’s making big moves. And a bride-to-be has to cut friends from the guest list.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represe...
Intuitive Laura Lynn Jackson joins Chelsea to talk about universal intelligence, signs from our loved ones who’ve gone before us, and how we’re all interconnected in ways we may never know. Then: A new mom seeks contact with the husband and daughter she lost. A couple struggle with their desire to pursue a relationship with a surprise sibling. And a daughter seeks to heal her relationship with her mom, even ...
Scotty James joins Chelsea to talk about why his wife is the CEO of his life, his longtime rivalry and friendship with Shaun White, and argue about why snowboarders are just *cooler*. Then: An expat in Greece needs to have a money conversation with her new man… but is it too soon? A skier wonders if she should transition to snowboarding. And a wife-turned-Instagram Girlfriend has lost her love for the slopes.
&nb...
Chelsea and Catherine get an update about a husband’s sexting ways, and a 20-something wants a baby… but is she ready?
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opini...
Josh Radnor joins Chelsea to talk about the highs and lows of playing one character for a decade, the delights of NYC, and his sober-curious lifestyle.
Then: A newlywed discovers an attempt at cheating while snooping on her husband’s phone. A sister wonders if she’s third-wheeling with her brother and his girlfriend. And an employee wants to do her job and make out with her boss. Just a little bit.
*
Emilia Clarke joins Chelsea to chat about learning Russian, her road to recovery after two brain hemorrhages, and how to pretend a tennis ball is a dragon. Then: An Argentinean’s messy habits have his boyfriend busy doing cleanup. A girlfriend is crazy about her new guy, but wants to maintain her single identity. And a newly-sober caller is comedy-curious.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@...
Chelsea and Catherine get a long-term update from a polygamist’s sister, and a couple calls in precisely because they have no problems.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent...
Drag superstar Monét X Change joining Chelsea to talk about the best party drugs, the scourge of bunions, and everyone’s favorite subject: boofing. Then: A listener’s inheritance has everyone passing by with their hand out. A deadbeat dad wins the lottery. And a friend of Monét’s needs advice on their out-of-drag career.
*
Need some advice from Chelsea? Email us at DearChelseaPodcas...
Kaitlin Olson (Hacks, High Potential, It’s Always Sunny in Philadelphia) joins Chelsea to chat about juggling 3 shows at once, forcing her husband Rob Mac to fall in love with her, and why balls are funny… until they’re not.
Then: A postal worker can’t jibe with girls her own age and finds happiness in may-december friendships. An ex-wife struggles to name a newborn. And an ex-stripp...
Chelsea and Catherine get an update from a caller who married his longtime love and assess a friend-zoning situation.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartM...
Kumail Nanjiani (OH MARY!, Night Thoughts) joins Chelsea to talk about building trust in a relationship, surviving the loss of his cat Bagel, and why working out is actually very nerdy. Then: A doggy deal breaker is just the tip of the iceberg in one man’s troubled relationship. And tension around tipping leads to an embarrassing situation for a restaurant’s regular.
*
Actress Toni Collette (Wayward, Goodbye June) joins Chelsea to talk about why Rome is her happy place, what it feels like to get your character wrong, and finding her inner creep for her role as a cult leader. Then: A baby actor struggles to leave his family to pursue his career. A stepmom struggles to connect with her stepdaughter after a sibling is born. And a sister’s tactless behavior results in an awkw...
Chelsea and Catherine talk with a couple exploring the foster system… for the second time.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or ...
Amanda Seyfried (The Housemaid, The Testament of Ann Lee) joins Chelsea to talk about auditioning for Wicked, mucking stalls on her farm in the Catskills, and why she’ll never do a stage play again. Then: A wedding in Bali threatens to go off the rails when an evil stepmother needs to be disinvited.
And a florist falls in love with an Ecuadorian rose merchant and wrestles with following her head or her heart...
Ross Mathews & Wellinthon Garcia-Mathews are here to talk about RuPaul’s best advice, early bedtimes, and putting a saddle on life. Then: A drag performer wrestles with a change of heart about their artform. A 30-something wants his firefighter boyfriend to open up. And a year-long relationship gets put back in the closet when one woman struggles to tell her family she has a girlfriend.
*
Oscar-winner Da’Vine Joy Randolph joins Chelsea to discuss the tea on Shakespeare, how to develope emotional fortitude early, and why she’ll never bring a man onto the red carpet. Then: The girls break up no fewer than two engagements. A traveler gets dumped by his boyfriend just before their European getaway. A corporate drone is desperate to get out of the office and into the great outdoors. And a May-Dece...
Elizabeth Olsen joins Chelsea to chat about why she swims naked every morning, her thoughts on reincarnation, and why she’s the perfect woman for a man with a fish pic in his bio. Then: A guncle wants to help his niece steer clear of becoming a Mean Girl. A single mom struggles to connect on the apps. And a young lawyer can’t get her man to commit - so she’s stuck paying double rent.
*
Chelsea and Catherine get an update from a caller whose bestie is about to be barefoot and pregnant. Then: A boyfriend struggles with asking his partner to open things up.
*
Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com
*
Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
*
*
*
The views and opinions expressed are solely those of the Podcast author, or individuals participating ...
The Daily Show’s Roy Wood Jr. joins Chelsea to talk about the life lessons he learned from unexpected people, why nobody wants to do you a favor unless they have an ulterior motive, and debate whether his parents had an open marriage way before it was cool. Then: A 40+ standup wonders where to focus her time. And a comedy-adjacent New Yorker tries not to become a Chuckle F*cker.
*
Popular Podcasts
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.
The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.
Listen to the latest news from the 2026 Winter Olympics.
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com