In this episode, the hosts kick off by discussing their Memorial Day plans. Craig seeks advice from Austen on how to handle his first pool party. They proceed to delve into Craig's upcoming weekend in New York, including his anticipation of attending his first Yankees game. However, there's a twist as someone special discourages him from wearing Orioles colors. Transitioning to television talk, Craig and Austen share their thoughts on the recent Vanderpump reunion show. They express their excitement for the upcoming second part of the reunion in the following week. Finally, they conclude the episode with lively debates and tackle a question about how they would divide the responsibilities in a triathlon relay among themselves—Craig, Austen, and Nick.

In this episode, Craig Conover and Austen Kroll are finally joined by Madison LeCroy. She is in the studio to address past "controversies" involving someone other than (A)usten. They then delve into Austen and Madison's relationship, discussing how they have managed to get along now that the dust has settled from their breakup. Madison also opens up about the challenges of being a mother on TV and how she deals with the misconceptions that have arisen while being in front of the camera. Craig, Austen, and Madison explore various topics from their world, and conclude the show by answering some questions from their besties.

In this episode, the boys bring you the podcast from different locations on the East Coast. Craig is up in New York with Paige, while Austen is holding down the fort in Charleston. The guys start by discussing how turbulence on a plane can bring everyone together, as "near-death" experiences often do. After the break, Craig and Austen dive into the world of technology, discussing both the exciting and unsettling aspects of the potential of AI. They also touch on controversies surrounding new social media and internet law proposals. The episode concludes with Craig sharing his thoughts on the moon landing, and the guys answering a few questions from listeners.

Craig and Austen are once again joined by Shep as they discuss and debate a wide range of topics. Shep shares with the guys about his stand-up routine and how much he enjoys doing it. Finally, the trio delves into a highly-requested topic, as they break down one of the biggest scandals in recent reality TV memory, and each gives their own opinion on the matter. After the break, Craig, Austen, and Shep engage in one of their trademark TV fights, which have become quite common. Finally, they wrap up the show by answering some bestie questions.

After a 2 week hiatus, Craig and Austen are back to share what they have been up to. From Aspen, to LA, and then New York the boys have traveled all over the country. The guys break down what it was like their first time filming reunions and how fun and intimidating it can be to sit down with Andy. They then dive into some of the recent country music drama from concert cancelations to T. Swift's breakup. Austen tells Craig he wants to be more touristy when they travel and Craig then gives Austen his recent tv and movie recommendations as they close out the show with some listener questions.

In this episode, Craig and Austen go old school. They will be discussing all of the different travels they have coming up, as Craig preps to restart "Travels with Craig. They then dive into all of the different "trips" Austen has made out to Red Rocks when he was living in Colorado and of course breakdown their excitement for the new Harry Potter series. Lastly, the boys throw it back in the question segment as Austen goes through some of his favorite DMs he has gotten recently.

In this episode, Craig and Austen are joined by Candice Horbacz. The host of the "Chatting with Candice" podcast discusses with the guys a wide array of topics: from healthy relationship roles and values to the benefits of plant-based medicines. Candice then gives some of her tips to answer some of our more popular and common best friend questions as she breakdowns ways couples can get more comfortable and honest with one another. You can find her podcast at https://www.chattingwithcandice.com/ or wherever you get your podcasts. Thank you to Gametime for sponsoring this podcast. Download the Gametime app, create an account, and use code PILLOWSANDBEER for $20 off your first purchase.

In this episode, the boys talk about why they have been so busy and the projects they have been working on. Craig and Austen discuss their excitement as they prep for the opening of Carriage House and Craig gets ready for Sewing Downs South 4 year anniversary on April 1st. The guys then discuss some other fun topics and close out with some questions from Besties! Also, a shout-out to Nick's cousin Lauren and her new husband Josh, who got married this weekend and is part of the reason this podcast is a little delayed.

In this episode, the boys are back from their trip and discuss some recent travel stories before they dive right into some of their Oscar takes. From Craig's views on some of the red carpet controversies to Austen talking about the winners and losers of the Academy Awards. Austen then helps Craig fill out his bracket as the boys discuss March Madness as Craig knows nothing about college basketball, but we look forward to challenging all who entered our bracket challenge. Lastly, the boys close out with some questions from some of our best friends!

In this episode, the boys discuss a wide range of pop culture topics. From Lady Gaga's lawsuit to the Angkor Crown Jewels of Cambodia being returned as Craig breaks down the many legalize of a ransom vs. a reward. They dive into their thoughts on this season's "Outer Banks" as Craig is sucked in but certainly has criticisms. Craig and Austen laugh about Craig's new "pranking" phase and then get involved with some old-school food debates that are making their rounds on the internet again about whether pineapple belongs on pizza too whether chili is a soup. Lastly, they close out with some fun bestie questions.