In the second installment of Prison Pennies, Sasha and June dive back into the realm of prison penpalship as they grapple with the challenge of selecting the perfect inmate to correspond with. As they sift through a sea of inmate profiles, they candidly discuss their struggles in finding someone they genuinely connect with. With tales of swiping left on dating apps and the disconcerting trend of women disappearing after Tinder dates looming in their minds, they entertain a surprising notion: could writing to a prisoner actually feel safer than modern dating? June humorously compares the dynamics of dating apps to the unique interactions found in penpal relationships with inmates, sparking contemplation about the potential safety and authenticity such connections may provide. Amidst their trademark wit and tendency for delightful tangents, Sasha and June keep the conversation engaging and light-hearted, delving into off-topic discussions ranging from healthcare to encounters with panhandlers, and everything in between.