In this episode of Dating Is a Joke, Diana sits down with comedian Adam for one of the most open, funny, and unexpectedly thoughtful conversations yet.

Adam talks about being married for over a decade in a relationship that doesn’t fit neat labels (not open, not closed… just complicated), navigating trust, therapy, mental health, and what honesty actually looks like when it’s uncomfortable. They get into OnlyFans, strip clubs, parasocial relationships, communication, and why telling the truth matters when you want to grow old with someone.

They also talk comedy. Bombing. Open mics. Why silence is part of the job. How comedy has changed Adam’s mental health, his relationship, and his sense of purpose. Plus, a rapid-fire “this or that” segment that somehow covers sex timing, locked doors, babysitters, phone calls vs texting, and Paw Patrol deadlines.

It’s messy, vulnerable, funny, and very real.

Listener note: adult themes and language. Definitely not for kids.

Comedian Anna Penner joins Dating Is a Joke for an honest, hilarious conversation about dating in your 40s, red flags, icks, and realizing that sometimes… you are the red flag.

From queer dating and long-term relationships to dating apps, voice-note icks, bad profiles, and why none of us actually know what we’re doing, this episode proves that modern dating is messy, confusing, and oddly funny.

If dating has ever made you feel optimistic, exhausted, or deeply self-aware, this one’s for you.

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Dating in a small town is very different from dating in a big city and Ian Dickie has lived both.In this episode of Dating Is a Joke, comedian Ian Dickie joins Diana to talk about going from Red Lake, Ontario, to Toronto, navigating dating in a tiny community, and why ghosting hits differently when you’re guaranteed to see your ex at the grocery store.They get into:Dating in small towns vs big citiesComedy scenes, competition, and finding your peopleWhy some men are intimidated by funny womenVulnerability, boundaries, and emotional growthChoosing not to have kids — and being upfront about itRed flags, green flags, and learning the hard wayHow comedy creates connection (on stage and off)It’s thoughtful, funny, honest, and proof that dating stories don’t have to be wild to leave a lasting mark.🎡 Plus: Wheel of Dating Disasters + This or That questions.Subscribe for new episodes of Dating Is a Joke, where we take dating seriously… so we can laugh about it.👇 Follow Ian DickieInstagram: @i.dickie👇 Follow Diana BInstagram / YouTube: @dianabcomedy