All Episodes

May 16, 2025 71 mins

Are you concerned about your lack of experience, whether that's sexually, in a dating context, or time in long-term relationships? Maybe you feel behind in some way, and hesitant or fearful about telling a woman about your level of experience.

As Jason says, "For men in particular, it means something about you if you haven’t had sex."

If it took you a while to start dating, have sex, or get into a relationship (or if, perhaps, you're not there yet as of today), you're not alone!

Here we talk through Jason's experience around pursuing ("The hope was a girl would tell me they liked me, and THEN I would feel comfortable to make the move."); dating without a lot of sexual experience (“I was terrified of what a partner would think.”); and journey around overcoming these patterns ("When you have the right system, growth can happen pretty fast!”)

Listen on to feel more relaxed and empowered about your dating and relationship experience -- wherever you're starting from.

---

Memorable quotes from this episode:

  • "All my somatic, unprocessed wounding would come forward."
  • "There’s this deep sense of being behind."
  • "If you don’t like me, I get hooked on you in a sense."
  • "In my family, we were robots in the same house."
  • "He had people on his team to cross this divide."
  • "I kinda ended up with a partner that I don’t really like."
  • "Every man carries a few arrows in his heart."
  • "Who even wants me? What is my value to society?"
  • "It was hard to throw myself into a career when I didn’t know myself."
  • "Opportunity comes from connection."

---

Mentioned on this episode:

Mark as Played

Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.