Willie loses his virginity to lesbian. He proceeds to have a kid with this woman at the age of 16. We talk about raising a kid while also trying to live his life. In attempts to do a comedy show to help raise money for the Malibu wild fires, Willie finds himself starting an orgy. He also talks about utilizing the strategy to jack off before he knows he's going to have sex with someone and we discuss Willie's time as a reality tv show host and how that led to tons of sex.

This week we chat with Matt Artisan, founder of "The Attractive Man" where he uses his skills as a professional dating coach to help single men around the world grow their confidence and meet the women of their dreams. Matt shares his most effective strategies on how to approach people in person while still being yourself. We discuss how status and money can influence dating and if we think women will start asking men out as much as men ask women out.

Have you ever wanted to know if straight male cheerleaders enjoy looking up the skirts of women? Our guest Shapel Lacey will answer those burning questions for you. We explore his experience of being in his first real relationship as a man in his 30s. We find out that Nick, Caitlin and Shapel have all dated a coworker and we discuss what it takes to navigate that kind of relationship. We then talk about being friend zoned, flirting and leading people on. Lastly, sending and receiving nudes.

Dr. Cat, a licensed sex therapist, yoga master and podcast host joins us for another episode of Single AF. We start things off with the hot and moist topic of self pleasure, specifically as it relates to women. Dr. Cat gives tips on how to set the mood for a positive self pleasure experience. Nick shares a BDSM experience and cat introduces us to dungeons. We then discuss breakups, how to get over an ex and if it's a good idea to rekindle the magic with an ex.

We welcome special guest Alex Powers comes to the show! Do lesbians fake orgasms in the same way straight women do? Do you want to hear about periods, period sex, period cycles, going down on a period, period blood? Caitlin recounts how she nearly became a porn star. If you could only have 1 sex position for all of 2019 what would you choose? Alex wraps up the show with a great sex story.

The highly anticipated recap of what has happened in Nick and Caitlin's love life is here. This conversation quickly gets wild, including delectable opinions on anal, pubic hair, the usage of cologne, and talking about sexy stuff with your parents. I love this episode and you better believe you will love it too. Stay safe. Have fun. Love life.

In this episode Nick and his guest Caitlin discuss the travels of misplaced panties, they have a conversation about dildos and vibrators, and why you should never share "your number" with anyone. Caitlin also has a love interest that claims he will only sleep with people he "loves."

Nick sits down with his pal Carl to discuss hookups on road trips, eating out the booty, favorite and best sex positions and the continued debate of does height (not size you pervs)matter. This episode is entertaining and joyous.

Nick meets a total stranger Rachel, 38 years old, divorced, single and successful AF. What exiting stuff will they get into on this episode of Single AF?

Nick shares a tinder story that happened this week, then the two guys discuss if height should be mandatory on dating apps. Greg shares details about the dating app he is launching soon and we continue to look into why Nick is Single AF.