Best Undateable Podcasts (2025)

1
Over 35 And Undateable (Best Of) 42:36

19d ago42:36

42:36

In this episode, Jess and Stephanie get real about the crazy world of dating for women over 35. From navigating double standards and uncomfortable questions to the strange misunderstandings that often arise, they share candid thoughts on what it's really like to date at this stage in life. And, of course, no conversation would be complete without a…

1
For Such a Time as This 22:07

4d ago22:07

22:07

We explore the significance of Easter as a season of renewal and what it means to let Jesus breathe new life into areas of our lives that seem beyond repair. Through personal stories and biblical insights, we discuss how pride often prevents us from experiencing restoration and why sometimes feeling the hurt is necessary for healing. Do you have re…

1
Melissa Villaseñor: Overcoming Doubt and Finding Her Voice from AGT to SNL 1:52:16

11d ago1:52:16

1:52:16

Comedian and actress Melissa Villaseñor (Saturday Night Live, America’s Got Talent, Netflix’s Verified Stand-Up) takes her shoes off and joins Rick for a refreshingly honest episode. Melissa opens up about feeling embarrassed early in her career, the fear of not being funny, and learning how to trust her real voice — both on stage and in life. It's…

1
TALKHEAVY PODCAST EP:239 - Dressing SEXY in front of HER MAN 1:10:04

14d ago1:10:04

1:10:04

1ST HALF - FRESH OUT THE SHOWER 2ND HALF - SHE CHOSE VIOLENCE ON HER BABY DADDYBy Devinwade

1
TALKHEAVY PODCAST EP:238 - WOMEN PAY ME TO DOMINATE THEM 1:14:34

14d ago1:14:34

1:14:34

1ST HALF - ALL ABOUT BDSM 2ND HALF - DO YOU TRUST HER? OR YOUR FRIEND?By Devinwade

1
TALKHEAVY PODCAST EP:240 - I WENT & GOT HIS WIFE’S NAME TATTED ON ME 1:36:59

14d ago1:36:59

1:36:59

FEAT: JAILA SHAE FUNNYNULLQUILL & LIL NICKY 1ST HALF - JUST GOT FIRED 2ND HALF - STORY TIME WITH LIL NICKYBy Devinwade

1
Adam Ray & Brent Morin (EPISODE 300!!!) 1:31:35

17d ago1:31:35

1:31:35

Episode 300 for TSYO. Episode 25 for Adam Ray. Episode 9 for Brent Morin. Take your shoes off for our 6th Anniversary of TYSO. RICKY'S ON THE LOOSE TOUR dates & tickets here: https://www.punchup.live/rickglassman Portland, ME • San Jose, CA • Los Angeles, CA, Grand Rapids, MI, Dana Beach, FL, and MORE CITIES COMING SOON - sign up for my e-mail list…

1
Harland Williams 6.0 1:49:56

25d ago1:49:56

1:49:56

Harland Williams takes his bakes off for the 6th time to talk with Rick Glassman. Don’t believe me? Give this a watch. RICKY'S ON THE LOOSE TOUR dates & tickets here: https://www.punchup.live/rickglassman Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, CA and MORE CITIES COMING SOON - sign up for my e-mail list to be notified when I'm c…

1
Joe Santagato (The Basement Yard) 1:52:55

1M ago1:52:55

1:52:55

The Sleepover Series, New York edition, continues this week with Joe Santagato. Joe hosts the wildly popular podcast, The Basement Yard, along side his co-host, Frank Alvarez. Frank was scheduled to take his shoes off along side Joe, but for reasons that you'll have to listen to in this podcast, he couldn't make it. If you like people talking into …

1
TALK HEAVY PODCAST EP:237 “WOMEN WANT MEN TO SUFFER” 1:28:46

1M ago1:28:46

1:28:46

1st Half- GO FUND ME SCAMMER 2nd Half- JUST SAY MIAMIBy Devinwade

1
TALK HEAVY PODCAST EP:236 “GETTING CASHAPPS IS CHEATING” 1:32:46

1M ago1:32:46

1:32:46

1st Half- SHE GOT HER BODY DONE 2bd Half- CASH BACK THEM CASHAPPSBy Devinwade

1
Iron Sharpens Iron: The Power of Christian Brotherhood w/Ben Sutphin 21:39

1M ago21:39

21:39

What happens when men drop the tough-guy act and actually show up for each other? In this eye-opening conversation with guest Ben, we dive deep into what authentic male friendship looks like beyond surface-level church groups. Ben shares the moving origin story of his unusual men's group, which began in 2008 when he committed to weekly meetings wit…

1
Mark Normand 5.0 (Sleepover Series NEW YORK edition) 1:55:25

1M ago1:55:25

1:55:25

Mark Normand (We Might Be Drunk, Tuesdays with Stories) visits Rick in studio to podcast. Don't believe me? Well, you might want to check out this episode to see. RICKY'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman Madison, WI • Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, C…

1
Are You Garbage 2.0 (Sleepover Series NEW YORK edition) 1:50:18

1M ago1:50:18

1:50:18

The Are You Garbage Boys (Kevin Ryan and H. Foley) take their shoes off for the second time... This time in a New York hotel (last time was in New Jersey. Watch it here: https://www.youtube.com/watch?v=Sm9tUmyOCdA). Check out their Route 66 Tour | Comedy Special (2025) here: https://youtu.be/OSkJS1gCDR4?si=R11L25qGvxo7ai1- RICKY'S ON THE LOOSE TOUR…

1
I've Got All My Sisters With Me 25:02

2M ago25:02

25:02

Celebrating Women's History Month by honoring the remarkable women who've shaped both world history and our personal journeys. From Susan B. Anthony securing our right to vote to Rosa Parks standing firm for justice in 1955 to Amelia Earhart breaking aviation barriers in 1932, these historical trailblazers remind us of the relatively recent struggl…

1
TALK HEAVY PODCAST EP:235 - LADIES GOT BBCs TOO 1:01:32

2M ago1:01:32

1:01:32

Today our special guest is MIMI WITH THE CAKES AND TAY TAY ! LIVE SHOW TICKETS: https://www.livenation.com/event/vv1AeZka6GkdiIbHt/sip-talk-heavy 1ST HALF - SHE SLEPT WITH BOTH BROTHERS 2ND HALF - SMOKES AROUND HER KID #PROSTITUTE #handicap #TALKHEAVYPODCAST #deliciousBy Devinwade

1
TALK HEAVY PODCAST EP:234 - MY BESTFRIEND IS A PROSTITUTE 54:09

2M ago54:09

54:09

Today our special guest is THE OPEN FLOOR PODCAST ! LIVE SHOW TICKETS: https://www.livenation.com/event/vv1AeZka6GkdiIbHt/sip-talk-heavy 1ST HALF - DATING MY COUSINS EX 2ND HALF - MY FRIEND IS A PROSTITUTE #PROSTITUTE #handicap #TALKHEAVYPODCAST #deliciousBy Devinwade

1
Jay Mohr (feat. Rick's Dad and Cousin Teddy) 1:45:44

2M ago1:45:44

1:45:44

Jay Mohr takes his shoes off then meets Rick's Dad & Cousin Teddy. RICKY'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman Brookfield, WI • Minneapolis, MN • Madison, WI • Sacramento, CA • Portland, ME • San Jose, CA • Los Angeles, CA and MORE CITIES COMING SOON - sign up for my e-mail list to…

1
Casey Abrams & George Krikes 3:19:51

2M ago3:19:51

3:19:51

Casey Abrams (sings the TYSO Theme song) and George Krikes (TYSO house musician) join forces WITH their shoes off for this very musical friend episode. PATH is ending homelessness for individuals, families, and communities. They do this by building affordable housing and providing supportive services throughout California. https://epath.org Support…

1
Letting Go: Sentimental Clutter and Spiritual Growth with Jess & Steph 19:08

2M ago19:08

19:08

Could your closet be the key to understanding your deeper emotional ties? Join Jess and Steph as we humorously unpack the sentimental attachments that make parting with personal belongings so challenging. From cherished band memorabilia to well-worn book collections, our conversation turns clutter into a canvas for storytelling and self-reflection.…

1
TALK HEAVY PODCAST EP:233 - OUR GUEST HAS 47 WIVES 1:06:20

2M ago1:06:20

1:06:20

Today our special guest is Hebrew Israelite Captain Tazaryach ! 1ST HALF - LET IT GO 2ND HALF - HELPING AN AFRICAN #Tazaryach #hebrewisraelites #hebrew #hebrews #chrislamBy Devinwade

1
Grace Kinstler (feat. George Krikes) 2:41:10

2M ago2:41:10

2:41:10

Grace Kinstler, American Idol top 3 finalist, takes her shoes off for the first time. Rick found Grace's singing on instagram a few weeks ago, then invited her onto TYSO the next time she was in LA. So happens that she was coming to LA to record acoustic videos for her music -- and of course we invited TYSO Music Legend, George Krikes to play and s…

1
THE TALK HEAVY PODCAST EP:232 1:05:57

2M ago1:05:57

1:05:57

1ST HALF - THIS DUMMY CONFESSED 2ND HALF - LET ME GETA NUMBER 1

1
TALK HEAVY PODCAST EP:231 - “3 KID MOMs ARE UNDATEABLE” 1:02:02

2M ago1:02:02

1:02:02

1ST HALF - THE 5 CHILD CHEATER 2ND HALF - MY BUSINESS IS MY BUSINESSBy Devinwade

1
Can't We All Just Get Along 19:34

2M ago19:34

19:34

What happens when love and faith intersect in a world that's often divided? Join us as we explore this profound intersection, sharing stories and insights that challenge the status quo. Through heartfelt discussions, we express our concerns about the growing negativity on social media and the struggle to maintain kindness and respect, even among be…

1
Annie Lederman 2:08:10

3M ago2:08:10

2:08:10

Annie Lederman (Anniewood) takes her shoes off for the first time with Rick Glassman as they talk about stuff. Watch on YouTube here: https://youtu.be/mMTN-ad64yU Support TYSO by supporting out sponsors: For the first time get the 24 hour pack. Focus and Sleep shots, bundled up for the at a 45% off, exclusive at https://www.magicmind.com/tysojan. T…

1
TALKHEAVY PODCAST EP:230 - "MY NEW BOYFRIEND BEAT UP MY SON" 1:05:33

3M ago1:05:33

1:05:33

1ST HALF - UNFORGIVABLE CRUSHES 2ND HALF - WHO'S THE ALPHA?By Devinwade

1
Dax Flame 2:02:16

3M ago2:02:16

2:02:16

Dax Flame takes his shoes off and talks with Rick Glassman about stuff. Love on the TYSO Spectrum. Watch on YouTube here: https://youtu.be/PAWP6-Z9ZvI Support TYSO by supporting our sponsors: Go to https://www.helixsleep.com/tyso for 20% off sitewide + 2 free dream pillows with mattress purchase. Download the DraftKings Sportsbook app and use code …

1
Love Is... 18:49

3M ago18:49

18:49

Join us for a heartfelt and humorous episode of the Jesus Fix It podcast as we explore the insightful world of love languages. Jess and Steph share personal stories and insights into how understanding the five love languages can transform relationships and bring deeper meaning to self-love. From words of affirmation to acts of service, they delve i…

1
TALKHEAVY PODCAST EP:229 - PORNSTARS ARE NOT HOES 1:00:00

3M ago1:00:00

1:00:00

1ST HALF- BEAUTIFUL BLACK BROKEN WOMEN 2ND HALF - CLAIMING FAKE BODIESBy Devinwade

1
TALKHEAVY PODCAST EP:228 - CHILD SUPPORT AIN’T FOR STEPKIDS 1:02:43

3M ago1:02:43

1:02:43

1ST HALF - STEP KIDS DONT MATTER 2ND HALF - MY SON RUNNING HOESBy Devinwade

1
Kyle Kinane [The Sleepover Series - PORTLAND] 1:53:51

3M ago1:53:51

1:53:51

Rick performed at The Helium Comedy Club in Portland then stayed a few extra days, where he met Kyle Kinane who was performing at the same club. Don't believe me? Check this ep out. Watch this episode on YouTube here: https://youtu.be/Z9Jb407y9ag Support TYSO by supporting out sponsors: This episode is sponsored by Better Help. Visit https://www.be…

1
Jon Rudnitsky 5.0 + SPECIAL GUESTS [TYSO Live] 1:57:10

3M ago1:57:10

1:57:10

Jon Rudnitsky (SNL, Curb Your Enthusiasm) makes his 5th appearance on TYSO -- this time live in LA, in front of 100,000* people. A surprise TYSO favorite(s) may or may not make an appearance as well... Support TYSO by supporting our sponsors: If you were wondering what drink Rick takes before most podcasts, it's called MAGIC MIND. Focus and Sleep s…

1
Dupe That 20:30

3M ago20:30

20:30

Is it wrong to crave the allure of luxury, or can you satisfy your style desires without splurging your savings? On today's Jesus Fix It podcast, we dig deep into the heart of "dupe culture" and how it’s reshaping fashion and lifestyle choices. Remember when toting a Guess or Coach bag was the ultimate status flex? We share a nostalgic laugh over t…

1
TALKHEAVY PODCAST EP:227 CHOOSING MEN FOR MY WIFE! we went to a swingers club 58:25

4M ago58:25

58:25

1ST HALF- "MY HUSBAND'S PORN ADDICTION" 2ND HALF - CHOOSING A SEX PARTNER FOR MY WIFEBy Devinwade

1
Ari Shaffir 4.0 1:26:18

4M ago1:26:18

1:26:18

Ari Shaffir takes his shoes off for the 4th time to talk about his new Netflix special America’s Sweetheart out now, and yada yada yada. Watch this episode on YouTube here: https://youtu.be/VjM9Rcrvrvg Support TYSO by supporting our sponsors: Stop putting off those doctors appointments and go to https://www.zocdoc.com/tyso to find and instantly boo…

1
TALKHEAVY PODCAST EP:226 “SEX AINT FOR BROKE MEN” 1:16:22

4M ago1:16:22

1:16:22

1st HALF: SHE WINT GIVE ME QUIET TIME 2nd Half: AGE GAP ISSUES!By Devinwade

1
Sona Movsesian 6.0 2:44:58

4M ago2:44:58

2:44:58

Sona Movsesian (Conan O'Brien Needs a Friend podcast, "World's Worst Assistant") is one of Rick's dear friends, and we welcome her back for her traditional annual January episode. She takes her shoes off for the 6th as Rick Needs a Friend. This is a more vulnerable episode for Rick than the traditional TYSO. He almost... "He"... Hi, I'm Rick, and I…

1
Allow Us to Reintroduce Ourselves—This is Jesus Fix It! 17:00

4M ago17:00

17:00

Join us for an engaging and heartfelt episode as we celebrate new beginnings and welcome Steph as a permanent co-host of the Jesus Fix It podcast! As we embrace the fresh start of a new year, we discuss our aspirations for 2025, focusing on personal goals and the universal longing for peace and harmony. We express our heartfelt gratitude to our lis…

1
TALKHEAVY Podcast Ep:225 - BREAKING UP WITH MY STEPDAD 54:26

4M ago54:26

54:26

1st Half - Mom called me a Coon 2nd Half - Crack Baby TherapyBy Devinwade

1
Talk Heavy Podcast Ep:224 CHEATING WOMEN DON'T WANT FORGIVENESS 59:52

4M ago59:52

59:52

FIRST HALF - FIGHT OVER EXES while in a Relationship SECOND HALF - SHE DON'T WANT TO BE FORGIVENBy Devinwade

1
Santa Clause 4.0 1:15:32

4M ago1:15:32

1:15:32

Santa Clause comes down the TYSO chimney with his shoes off for another round of talking and stuff. Merch @ https://www.rickglassman.com/store RICK'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman Los Angeles, CA • San Diego, CA • Phoenix, AZ • Eugene, OR • Portland, OR • Denver, CO • West Jo…

1
Harland Willams 5.0 2:22:37

5M ago2:22:37

2:22:37

Harland Williams, Harland Highway, blah blah blah. RICK'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman Los Angeles, CA • San Diego, CA • Phoenix, AZ • Eugene, OR • Portland, OR • Denver, CO • West Jordan, UT • Boston, MA • Philadelphia, PA • Brookfield, WI • Minneapolis, MN • Madison, WI • …

1
Family, Loss, and the Magic of Christmas with Jess & Steph 19:44

5M ago19:44

19:44

Growing up, the magic of waking up to a blanket of fresh snow was unbeatable, but the struggle of shoveling and navigating icy roads was a stark reality check. In this episode of the Jesus Fix It Podcast, we reflect on those mixed feelings about winter's wonderland. We embrace the enchantment of snow days, where warm drinks and beloved holiday movi…

1
TALKHEAVY PODCAST EP:223 - MY BOYFRIEND STRIPS FOR MEN 56:52

5M ago56:52

56:52

1ST HALF - TIPPING MY HOMIE STRIPPER 2ND HALF - WHY NOBODY LIKE FAT PEOPLE THE TALK HEAVY PODCAST EPISODE - 223By Devinwade

1
TALKHEAVY PODCAST EP:222 - MY EX-GIRL used our MISCARRIED BABY'S NAME WITH HER NEW MAN 1:05:42

5M ago1:05:42

1:05:42

1ST HALF - THE STOLEN NAME 2ND HALF - DEV'S TRUTH THE TALK HEAVY PODCAST EPISODE - 222By Devinwade

1
Ashley Christine [A SCIENCE EPISODE] 2:14:43

5M ago2:14:43

2:14:43

Ashley Christine (Modern Day Eratosthenes) is a STEM (science, technology, engineering and mathematics) content creator that Rick discovered a couple years ago. Her content is so interesting, Rick invited her to take her shoes off to talk all things science, space, and nerd. Follow her here: https://www.tiktok.com/@modernday_eratosthenes https://ww…

1
Adam Ray & Brent Morin 1:54:53

5M ago1:54:53

1:54:53

The Best Friend's Club is back! Brent Morin and Adam Ray come over and get silly with Rick Glassman. Don't believe me?! Give it a listen. RICK'S ON THE LOOSE TOUR! My new US stand up tour! Dates & Tickets here: https://www.punchup.live/rickglassman JJanuary 8th San Diego, CA • January 9th Phoenix, AZ • January 15th Eugene, OR • January 16th Portlan…

1
Misconceptions Unpacked with Jess & Steph 25:35

5M ago25:35

25:35

In this engaging and honest podcast, Stephanie and Jess dive into the complexities of cultural understanding, addressing stereotypes, misconceptions, and sometimes awkward but necessary questions about race, culture, and identity. With humor and warmth, they create a safe space to explore topics like Black hair care, cultural appropriation, food ha…