On this very special episode of The Tough Questions Podcast. The boys sit down with comedian Mae Planert. They talk about Mae recording her new special. What the plan is down the line. Having children and what is Mae's retirement goal. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagr…

On this very special episode of The Tough Questions Podcast the boys have on Comedian Anthony Moore. This is a very chill departure from last week with Nathan MacIntosh. Anthony does well withstanding the head of Jeff's TQs. This is a fun episode thank you all for watching we hope you enjoy. Ask Your Own Question Sign Up for The Patreon HERE! www.p…

We are BACK and it's a big week - Mae’s special has been taped! The ladies go over how hard Mae crushed, the aftermath *flees to Puerto Rico*, and more! We also go over Caitlin Clark's insultingly low salary, Rat birth control helping NYC rats move away from abstinence-only education, the mysterious deaths of TikTokers (and JLo's involvement?). We …

On this very special episode of the Tough Questions Podcast the boys have on comedian Nathan Macintosh (The Tonight Show). We get do to the nitty gritty of what makes comedians different. What would Nathan rather be Taller or Smarter and all other kinds of amazing TQs Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestion…

Diddy did it? This week we are talking about the now infamous Sean Combs and the Epstein-like drama that has built after a CONCERNING amount of allegations have come out against the media mogul. In Part 1 of 2 we are talking about how Diddy got to where he is today. We review his early days at Uptown Records, the creation of Bad Boy entertainment, …

On this very special episode of Tough Questions we have comedian Ali O'Neil on. She talks about growing up Boston trash. What it was like to have a very kind but alcoholic mom. Jeff doesn't do ENOUGH research on this one. And Tim annoys everyone.By toughquestionspod

On this very special episode of The Tough Questions Podcast we have friend, comedian, and super fan Matt Bachus on the show. Matt opens up about childhood trauma and mending his relationship with his dad. Tim has to apologize to Matt's mom for being a jerk. And Jeff lays down some very good TQs for Matt's As. Ask Your Own Question Sign Up for The P…

We’ve got a hot one! This week on the pod the ladies break down some short stories to kick off April and break down over Mae’s upcoming special taping (anyone got the number of a therapist?). We start off with a controversial new Online Harms Act in Canada that may impact free speech on the internet. Spicy! We then talk about the best employer out …

The ladies have possibly their darkest episode to date! No kids for this one you guys (but seriously… trigger warning for cannibalism?!) We start off light with a story that will have you breaking your ankle running to the comments? The yogi burglar that got their vinyasa on before robbing a bakery for some hot cross buns. The ladies then cover the…

On this week's episode of Tough Questions we have comedian Chris Scopo. We talk about growing up in New York, worst childhood memories and wild accusations about the state of Indiana fly around the studio. We hope you all really enjoy this one. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://ww…

This week on the pod we’re ruining your spring break travel plans with the play-by-play on Boeing’s plane failures. We’re talking losing wheels on takeoff, engines catching fire, the infamous Alaska airlines door blowout, and a concerning amount more. We then go over the whistleblower, John Barnett, who was unalived in the middle of testifying agai…

On this very special episode of The Tough Questions Podcast. We have Comedian and long time friend of the boys Joe bates on the show. He gives some great As to his TQs and tells the boys he is moving to Denver. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeffrey/ Fo…

We've got the hilarious Anna Bianco on the pod with us. First up, Anna spills the beans on some serious workplace drama at American Apparel, namely being possibly the only employee to NOT be harassed. Then, we dive into the cutthroat competition of being a George Washington Museum tour manager. For our weekly topics, we've got some m*rder for ya. W…

We're talking the big world changing issues - Sydney Sweeney bringing America back into our boob era. We also cover the Miami crackdown on fun, the 90-Day fiance colon cancer scam and the viral Willy Wonka experience that left children in tears. Follow us @risquebusinessnews @laurasogar @mae_planert and write us a kind review for a good old fashion…

On this very special episode of Tough Questions Podcast the boys talk to Casey Balsham. She gives her honest As to some pretty serious TQs. We talk motherhood, advice for young women and do some overall comedy talk. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeffre…

On this week's episode of Tough Questions the boys have on Molly Brenner. Molly does her best to gives As to Jeff's TQs but struggles on some. This is a really fun episode. We hope you really enjoy it. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeffrey/ Follow Tim …

This week on the pod the ladies are talking the #GotProof lawyer, Nicole Fegan, who got so involved in her trial with gang YSL (not Yves St Laurent) that she ended up locked up herself. We check in on our boy SBF who is making friends in jail and get an update on Neuralink human trials. We also discuss the Momfluencer, Ruby Franke, who got locked u…

This week we’ve got a story we can’t even believe is true - the time that eBay cyber-stalked (and in-person stalked) a Massachusetts couple for writing them a bad review. Talk about not being able to take a dose of your own medicine! The girls go into the story of Ina and David Steiner who ran the newsletter and website, EcommerceBytes for sellers …

On the pod this week the boys have The Asian Sensation himself Garri Madera. This is a great episode. Garri is very open and honest with Jeff's TQs. I hope you all enjoy. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestionsBy toughquestionspod

On this week’s episode, the ladies talk football! Filmed on Super Bowl Sunday we go over Game Day predictions and commercials of the past, yes this is coming out after the Super Bowl so you get the pleasure of hearing how stupid we sounded! There’s more though! Elon Musk hired his employee, Shivon Zilis, for an unusual task that definitely required…

This week on the show the boys welcome Matisyahu Nissim. Matisyahu tells us who he would beat up. What it was like growing up with older brothers. And how he dealt with being hime schooled as an Orthodox Jew. This is a super fun episode. We hope you all really enjoy it. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuesti…

On the tough Questions Podcast this week we have hilarious comedian Bobby Condon. He sits down with the boys to give his As to Jeff's TQs. We get deep into what makes Bobby tick on this episode. We also go through his past loves and what love will come. We hope you all enjoy this one. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.…

We've got a February story round-up! This week we're talking about the comeback story of the century *dramatic* - Shane Gillis's return to SNL as a host! 5 years after his off-color jokes got him fired, he's back as a guest host with a Budlight sponsorship thrown in the mix. Cheers to that! Then we chat about a viral tide-pod-inspired challenge swe…

We're pulling back the curtain on the dollars and cents behind THE celebrity PR (?!) relationship, Taylor Swift and Travis Kelce. Join us as we dissect the lucrative business of crafting public images that helped make the NFL an additional $330M this season. We also dig into the undeniable rise of NFL star Travis Kelce from the field to the cover o…

On this week's episode of The Tough Questions Podcast we have Bret Raybould (Race the Movie: The Play) Comedian, Filmmaker, Playwrite, and co-host of Better Halves with Lisa Ann. We get into it all on this one. Bret schools the boys on Reconstruction. He talks about what its like to have siblings that are all succeeding wildly. And how having a bac…

On this latest episode of the Tough Questions Podcast we have comedian Jack Comstock on. Jack's feet are held to the fire of Jeff's TQs. This is a super silly and fun episode. We hope you all enjoy it. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeffrey/ Follow Tim …

Bonus episode alert! Today on the pod we have a special guest, comedian, and friend of the pod, Felicia Madison. The gals talk about running Westside Comedy Club, a comedy school, reinventing yourself, and motherhood in the modern age. They also talk about which celeb relationships will stand the test of time; Taylor swift and Travis Kelce? Kylie a…

It's a modern-day Cinderella story! The girls talk about the story of Samsung heiress, Lee Boo-jin, who falls in love with her security guard and has to convince her Korean GDP-impacting family to let her start a life with him. Don't worry, as with all of our stories this one doesn't have a happy ending when he goes on to cheat on her (?!) and goes…

On this episode of Tough Questions the boys have on comedian Collin Chamberlin. This is a very fun episode. Collin does try to be funny a couple times but is swiftly shamed by the boys. Also a new fun twist to this one. Collin gets mad at Tim and not Jeff today. Hope you all enjoy. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com…

What do an exploding Dunkin Donuts toilets, that University Chancellor who had a side hustle in porn, a violated manatee statue, and the anti-surrogacy pope all have in common? They're some of the weirdest news we cover in this weeks episode. We start off with White Claw's lame attempt to get into the Dry January game by creating non-alcoholic Whit…

On this episode og Tough Questiosn Podcast. The boys have Myka Fox from The Great Hang Podcast and being in love with Tim. Jeff gets in deep with these TQs. Tim gets legit mad at Myka during the show. And all in all its a very fun show this week. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://…

You had to know we were going to do this one... the Gypsy Rose Blanchard story. Mae and Laura tell the story of a decades long financial and medical scam perpetrated by Dee Dee Blanchard. Unless you’ve been living under a rock, you probably know who Gypsy is by now, but do you know the full story? The girls cover her childhood, how her mom got away…

The boys have one of their good friends and comedians Tito Garza on the podcast. Tito is reluctant to answer some of Jeff's questions. Jeff does his best to pull the answers he wants from the guest. Tim is hanging having a great time being pretty on this episode. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Fol…

Happy New Year! We are back with a hot one - we're talking fraud in the billions with a B and possibly the most wanted man in the world, Jan Marsalek. Today's story is on the Wirecard disaster that high key embarrassed Germany's banking industry. We're focusing on wanted fugitive Jan Marsalek, the former high power Chief Operating Officer of Wireca…

Everyone loved Peter Wong so here is a little bit more for you. From deep behing the paywall of our patreon page we bring you more Peter Wong. See you all in the new year. And we hope you have a great day! Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeffrey/ Follow …

On this week's episode we have the Christmas Boy himself Tommy McNamara. We have had Tommy on the patreon before and that was an incredible episode. This episode is filled with holiday cheer and fun. I hope you all enjoy this one and have a wonderful new year. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow…

This week on the pod the ladies review some sensitive topics (and a guy who falls over his cat). We're talking "How to get Fired Guide" by Harvard, MIT, and UPENN Presidents George Santos on Cameo and his brush with Jimmy Kimmel Zara's questionable ad campaign The Chipotle Assault and its unusual punishment Follow us @mae_planert @laurasogar @risqu…

On this episode of the podcast we have another one of Tim's co-workers and comedian Adam Mamawala on the show. This is a fun one. We dive into life after a divorce and the circumstances on why it happened in the first place. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newy…

On this week's episode of Tough Questions we have comedian Jason Choi (Very Tall). Jeff opens the show with the most annoying question you can ask a tall person. Tim does his best to not be too much of an edge lord. We talk about Jason's days in an emo band and his struggles with alcohol. This is a great episode and I hope you all enjoy. Ask Your O…

This week on the pod the ladies catch up with the 19-year-old arch-nemesis of Elon Musk, Jack Sweeney! Jack spent his quarantine taking exams and aggravating Elon with his Twitter/X account @ElonJet that published open-source information on Elon's private jet's flight records. This transformed from a hilarious internet squabble to a historically no…

On this episode of Tough Questions we have comedian Jill Weiner on to discuss growing up in the south. Dating an older man in high school. And the perks of having a friends giving. There is a nice part in this episode where Tim realizes he was the only one not invited to Jill's Friends Giving. Ask Your Own Question Sign Up for The Patreon HERE! www…

Laura proposed! This week we go over the logistics of the woman proposing (WHY ISN'T THIS A THING YET?)! We talk about Laura's journeys in Asia including wet markets in Bangkok, beaches in Krabi, and the beauty industry in Seoul. We also go over some fun stories from November. Rivers of wine in Portugal! A finger found in a Chopt salad! 2 Million d…

It's the holiday season and if you think your family is dramatic... this week we talk about the lady who has made family drama big business, Jada Pinkett Smith. With the release of her memoir in the middle of WWIII, Jada doesn't want us to keep her name out of our mouth. We go over her history as a self-proclaimed drug dealer (entrepreneur!), the S…

On this episode of The Tough Questions Podcast we have guest Ahri Findling (Nickelodeon) on the show today. Ahri is Tim's boss and a hilarious comedian. This is a very fun episode. Ahri gets all kinds of mad at Jeff and Tim. If you like episodes where the guest struggles to have a good time this is the episode for you. Ask Your Own Question Sign Up…

On this episode of Tough Questions we have hilarious comedian Max Fine (In The Mini Van Pod). We talk about fears, growing up and everything that make us tick as people. This is a really fun episode. Max and Tim are on the same page a lot and it really annoys Jeff. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions F…

This week the ladies are joined by Sophie Buddle (Comedy Central, Tonight Show, Juno Award) and this episode is truly serving c*nt. We start off learning how the Canadian comedy scene works and break down how she got started in comedy at 14 years old (she made a lot of egg salad). Then we get into the important topics like Kim Kardashians nipple br…

This week the boys have on comedian Brittany Cardwell. They do a deep dive into why she hasnt been in love in 6 years. And her problems opening up to people. She also tells one of the saddest stories ever on the show. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www.instagram.com/newyorkjeff…

On this episode the boys sit down with comedian Elle Orlando. They get into it all on this podcasts. Dating, how you are in a relationship, and what top 3 things Elle brings to the table. This is a very fun episode and We hope yo all enjoy it! Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.com/ToughQuestions Follow Jeff https://www…

This week on the pod the ladies are joined by Erica Spera, comedian and host of dating podcasts Finding Mr Height and Shooters Gotta Shoot, to talk about the rise of AI relationships. From companies like Replika to influencers making their own AI bots, normal human people are opting out of dating other humans in favor of computers. Try explaining t…

We had our old friend Steven Castillo (SNL) on the show today. Steve is hesitatnt to open up around Jeff based on past experiences of Jeff bullying him. Steve also comes in hot and ready to go for Halloween. This is a super fun episode. Check it out on Youtube to see Steve's costume. Ask Your Own Question Sign Up for The Patreon HERE! www.patreon.c…