SHOW / EPISODE

429: Mid-life men: 3 categories of sex toys that'll rock your world! (ft. Karen Bigman)

58m | Sep 4, 2026

You've probably heard of penis rings. Maybe you've even tried one!? But there's a another tool almost nobody talks about — the men who've actually explored it say nothing else compares, and yet most guys never even consider it, because of one thing: shame.

Whether it's a marriage that's quietly gone sexless, an erection that isn't cooperating the way it used to, or just curiosity about what's actually out there beyond what you already know, midlife brings up a lot of questions men don't feel safe asking anyone — not their partner, not their doctor, not even their friends.

Karen Bigman gets it. A certified sex educator at 60, she's got 3 fun categories of sex toys she recommends for men. We get into things like: How does a penis pump actually work in real life with a partner — do you pause mid-makeout to grab it, or does it happen before you even get to the bedroom?

And we go somewhere most men never go: the prostate. What's it actually like? Why do the men who've explored it describe it like "watching in high def"? And how do you even start, solo or with a partner?

One stat that stuck with me: according to Mayo Clinic, erectile dysfunction can show up 3-5 years before any other symptoms of heart disease appear. Your body may be trying to tell you something before anything else does.

If you've ever been curious about exploring more but didn't know where to start — or didn't think it was "allowed" — this one's for you.

Work with us

Ready to go deeper than the podcast and take action? Jason and I help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)

Mentioned on this episode:

  • Karen's site: TabooToTruth.com
  • Please Her In Bed (Melanie's streaming course on how to talk about sex): www.pleaseherinbed.com
  • MyHixel — penis rings, and a premature-ejaculation training system
  • FirmTech — clip-on penis rings, including the Tech Ring (tracks nocturnal erections)
  • O-Nut — stackable comfort/bumper rings
  • MV Health (formerly Mystery Vibe) — vibrating prostate massagers
  • Aneros — prostate massagers
  • Maude (Shine) — lube I recommend

Memorable quotes from this episode:

  • "I think the sexiest thing a man can do is ask."
  • "Your penis health is a barometer of your overall health."
  • "It's like watching a show in high def."
  • "The two hardest conversations in relationships are sex and money."
  • "This is a guy that's actually, like, cares. This is a guy that wants to talk to me. He doesn't just want to get in my pants."
  • "'I don't care if I ever have sex again.'"
  • "60 is the new 60."
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Dear Men: How to Rock Sex, Dating, and Relationships With Women
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