Reflecting on all their conversations during season one, Oliver shares that he has learned that he is obsessed with money, specifically mixing sex and money. Although Oliver is a dirty free spirit, he stopped himself from starring in his own pornography for fear of professional repercussions. He has since realized that he hates wholesomeness and loves addiction and vices. Meanwhile, Teresa reveals that she has learned she was depressed from her prior toxic relationship with the cheating old man and that her depression stopped her from living a Hot Girl Summer. She talks about the steps she made to change herself, including her extreme weight loss and getting back out on the dating scene. Then Teresa and Oliver reflect on personality types and how some people are unforgettable in our minds while others can be easily forgotten. The episode wraps up with Oliver sharing his summer goals of making a short film about porn that he can submit to mainstream film festivals and making spicy content for his Onlyfans. Teresa reveals her plan is to get a summer romantic partner who adds to her life, not tries to change it.

Oliver usually only hooks up and never dates, but for the first time, he tried a speed dating event, where he was shocked to meet wholesome queer people. Meeting the wholesome people made him feel weird about himself and old, because his dates were all Gen-Z who did not know any of his pop culture references. Teresa reveals that she also wants to change her romantic behavior. Instead of being a dominant independent woman, she fantasizes about being a submissive pillow princess to a manly guy–like a fireman. The talk eventually leads to Oliver sharing that he wants to act in porn himself but that he holds himself back for mainstream career possibilities, and this shocks Teresa who views Oliver as someone who does whatever he wants. The two then talk about escorts and porn stars they know whose lives are enriched by their sex work money, and this leads them to explore the question, “What’s the point of saying no to something you actually want to do?”

Recently Oliver got a skin rash and thought he had syphilis. Luckily, it was just a viral infection, but the scare got him and Teresa to talk about trusting doctors, STDs, health insurance, and sex education. Teresa states that it is important who we pick to be with because they can ruin your life, and thrill-seeker Oliver shares that he has lots of sex so he tests for STDs every three months. Hopeless romantic Teresa reveals that she actually enjoys getting lovebombed, and Oliver jokes that she would’ve fallen for Armie Hammer. The conversation then takes a more serious turn when Oliver and Teresa talk about other dangers of sex besides disease, such as sexual assault, stealthing, and murder.

Teresa recently conquered her fear of solo traveling and took a day trip to Catalina Island where she met new friends since Oliver wouldn’t go. Oliver shared that he hates outdoor activities but that he loves to travel alone, especially to places where he can explore and find men on Sniffies. The two talk about how traveling can open your mind, and Teresa recalls a trip to Texas where a man with an Asian fetish wouldn’t leave her alone. The two agree that non-Asians having a sexual preference for Asians is actually great for them but there’s a line between preference and objectification. All of the chatting about traveling leads to talk about their favorite gym, Equinox, which has clean locations around the country, and this eventually leads to their discussion about how it’s okay to chase money. Oliver reveals he now only writes for money, and Teresa shares her life goal is to retire and travel.

Oliver starts the show by sharing his recent positive experience ingesting psilocybin mushrooms and the emotional crash afterward. Teresa talks about her own psychedelic trips and reasons why she doesn't need drugs anymore. They explore the authenticity of their sober and substance-altered selves, with Teresa preferring her sober self and Oliver leaning towards his substance-induced persona. The conversation shifts a little to the subject of Hollywood toxicity, specifically with the past hit show Lost, which makes the two question the essence of successful work created by flawed individuals. Oliver shares a saying that every filmmaker spends their entire life making one film or working on one idea. The two contemplate their own ideas and explore themes like loneliness and human connection. They also talk about their evolving attitudes towards money, negative influences, and the delicate dynamics of money in relationships. The episode ends with Teresa reflecting on her past romantic experiences with cheaters before she piques Oliver's attention with a cuddling service that she discovered.

Teresa and Oliver dive into the buzzworthy topic of ChatGPT, sharing contrasting experiences with it. Teresa has tried using ChatGPT as a therapy session, comparing it with platforms like BetterHelp, and Oliver talks about a friend who turned a script into a book using AI. The two discuss the impact of AI on various aspects of life, like jobs and relationships, but they agree that it cannot replace or replicate true real-life experiences. They also bring up a podcast episode they both heard and lessons they got from it, such as the significance of being out of the home and working on their personal growth. Teresa has been seeking excitement outside of comedy by signing up for Meetups and other live events. Oliver credits Exposure Therapy as one of his reasons to pursue comedy and practice his English skills. Teresa reflects on her motivation to write while Oliver struggles with procrastination but finds an outlook to create through the writing of his autobiography. The two end the episode by stressing the need to declutter one's life and to prioritize fulfilling experiences.

Teresa gets into an awkward situation at her gym on Mother's Day, and Oliver convinces her to join him at Equinox, which has clean steam rooms. The two delve into their thoughts on gym culture and their shared admiration of money-driven individuals working in unconventional industries. Oliver recounts tales of one past boss that demanded "obedience" and was obsessed with control tactics like calculating her employee's menstruation cycle. Teresa shares her perspective on balancing traditional values with aspirations in nontraditional industries. The two also touch on the sensitive nature of modern society and the intricacies of social media, especially OnlyFans. Shifting gears, Teresa expresses her readiness to embrace Hot Girl Summer and her experience with dropping hints on her crush and making the first move. Meanwhile, Oliver admits that he hasn't had a proper date in a while. The two round out the show with the type of guys they like and Oliver's story involving a roommate's struggle with winter-time self-pleasure.

Podcasting from Oliver's new [rented] house, Oliver and Teresa start things off by taking care of business--by talking about it. Oliver talks about his entrepreneurial journey from an e-commerce employee to an adult entertainment production company owner while Teresa speaks on the differences between corporate life versus freelance life. Oliver and Teresa talk about having Onlyfans accounts, and Oliver reveals a subscriber asked him to make a "macro fetish" video. He then recounts his recent attendance at exclusive sex parties in New York City and the unwritten rules there. The two later chat about bikini bars, caring bosses, risk-taking, and unsafe work environments. Teresa talks about how she wants to be a good business owner and how she is continuously inspired by Oliver's risk-taking mentality.

Oliver and Teresa talk about gender roles in relationships, specifically the differences between male and female providers. Oliver shares his recent sexual experience with a trans man while Teresa discusses her recent dating experiences of limited success. Oliver provides more details about his trysts with women, and Teresa expresses her perspective on the legalization of sex work. They also touch upon Oliver's cum dump parties and Teresa's challenges of maintaining an OnlyFans account. Finally, the two talk more about Beef spoilers, Ali Wong's new relationship, ambitious people, and their respective film school degrees.

Ali Wrong (Oliver) and Phil Miabals (Teresa) showed up in each other's clothes which sparked the conversation about masculinity vs femininity. This causes Oliver to reminisce about his childhood, sports, and facial hair. Teresa recalls her own struggles with her physical appearance growing up. Teresa admits that she thought Oliver was a twink when they first met while Oliver hates it when guys switch roles during sex. Teresa thinks stand-up turned her off from sex and that celibacy is a better choice than meaningless sex. Oliver shares that he was unmatched on a hookup app after the guy found out Oliver was a comedian. Oliver ends the episode by talking about a recent phone sex conversation he had before inviting Teresa to a cumdump.