Cookie introduces the second season while reflecting on past guests. While celebrating their accomplishments, she addresses expectations of exposing more of her dating life this time around and implementing more of the joy associated with unpacking dirty bags.

In this final episode of season 1, St. Louis entrepreneur, artist, and jewelry designer Jenni Lovette took a break from planning her XSKLOOSIV 100 NYE Celebration to come chat with Cookie about the why behind her larger than life personality. They discuss the beginning stages of her passion for designing and how a simple pair of earrings led to what would become Jenni Lovette Jewelry, her entrepreneurship journey, and the process/lessons of event planning. This raw uncut girl talk discussion unpacked everything from heartbreak, personal accountability, the conflict of public misconceptions while dating and tackling male insecurities, and why she would never judge the "DaniLeighs" of the world. This episode is everything you need to close out 2021. 

This bonus episode takes a look at the drama between rapper DaBaby and singer DaniLeigh. After this week's public battle between the two in his home and official public confirmation of him being the father of her 3 month old daughter, Cookie talks about the public reaction and even relives her early motherhood experience. Is "choosing better" really a guarantee to peaceful parenting? Is this DaniLeigh's karma for being colorist and her issues with the mothers of his current children? Is it truly time to cancel the DaBaby due to prior behavior? Cookie gives her take on the topic of babymama/daddy drama.

After the death of a former journalist and friend, Cookie brings back activist, and curator Kris Blackmon along with rapper/spoken word artist Ackurate to dissect the public struggles of being a creative. A revisit from Ep:2 "Creating Amidst Covid", they follow-up on topics including creative obligations while battling depression, making art reflect personal intersections and transformations, and the necessity of the magical word NO. This episode gives creatives a space to unpack the "what next".

 For part two, Cookie is joined by social media influencer Jess Deliseo discussing her time as a sex worker. She discusses how a combination of  revenge porn and a weight loss journey helped her become successful using the OnlyFans platform. Everything from how to establish high paying clientele, personal liberation, bullying from other women, to impacts on personal relationships, nothing is off the table. Bring a note pad, she's bringing the OnlyFans cheat code. 

The first of a two part episode, community organizer, healing support specialist, motivational speaker, author, and poet Tracy Stanton joins Cookie for a raw chat about her time as a former sex worker. She gets candid about childhood abuse, drug dealing turned use, incarceration, and self discovery through therapy. She dissects everything from sex work misconceptions, obsession with validation as a stronghold in the industry, to the importance of personal accountability and the dangers of bandwagon societal expectations.

Cookie rejoins Bre Ellis and brings in friend Tim Hall to expand on the topic of courtship and the pain points of dating from episode 20. They discuss everything from $1 first dates to prove humble worthiness to the breakdown of the movie "Baby Boy" and how Jodi was the actual victim. This episode is a candid unpacking of both the needs and misunderstanding of the opposite sex.

Cookie joins fitness coach Bre Ellis for a chat about dating, pseudo-love guru Kevin Samuel and his followers, and fuck boy behavior.

Cookie chats with resident guest Denetria Brijel about the launch of her blog denetriabrijel.com, controversy surrounding the Olympic disqualification of U.S. sprinter Sha'Carri Richardson for failing a drug test, selective allegiance to "rules are rules", double standards, and a sprinkle of dating. 

On the eve of her 39th birthday, Cookie reflects on the lessons of her 30's good, bad, and uncertain.