For over 16 years, Andrew, a real-life 40-year-old virgin, has been sending money to male inmates, hoping to find love. We applaud him for being brave enough to share his story on the podcast. Hear how much money he has sent to prison inmates, why he feels he does what he does, how he deals with the heartbreak, and other personal details of his life story.

Then, we speak via prison telephone with Kevin, author Inmate Intentions: The Truth About Inmate Scams and Prison Hustles. Kevin used to be a scammer from behind bars, but once he met his wife on a pen pal site, he decided to change his ways. Feeling bad about all the women he took advantage of in the past, he promises to atone for his ways and help others learn the red flags of inmate manipulation. Learn more about his miraculous transformation and hear what he feels is the biggest red flag to watch for when you're involved with a prison pen pal.

"From money requests to fake emergencies, inmates use calculated tactics to get financial support. Learn how these scams work and how to protect yourself from being exploited. Protect Yourself Before It’s Too Late. Many people don’t realize they’re being manipulated until they’ve already lost money and trust. This book gives you the tools to stay ahead, recognize the signs, and make informed decisions."

Last but certainly not least, we'll hear the clinical perspective on why inmates seek free-world pen pals, and why people on the streets so willingly send money to inmates. Kesley Rogers, a licensed professional counselor from Tennessee, actually worked as a Mental Health Technician at a state prison. She has years of experience in her field, and a degree in Forensic Psychology. Learn more about Kesley at Denney-Counseling.com.

Our hope, after hearing this episode, is that our listeners will be better prepared when entering a pen pal friendship or relationship. We hope people will understand that some (but not all) inmates are manipulative. And we hope, as Kesley Rogers would suggest, that we all start looking for our own "Why?" Perhaps then, and only then, will things start to make sense.