ICYMI - The Fear of Being Alone—and how do we know if we’re stuck

ICYMI - The Fear of Being Alone—and how do we know if we’re stuck

What happens when we carry old attachments into new relationships? Jen Kirsch and Tony Tedesco join to unpack the concept of “monkey barring” in dating, the fear of being alone, and how emotional attachments shape our choices. The conversation explores the role of self-awareness, when it’s healthy to step back from dating, and why letting go of the past is key to growth. They also share practical advice on solo travel, discovering connection in unexpected places, and embracing experiences that build resilience.

Guest: Jen Kirsch, Tony Tedesco

Originally aired on 2025-09-05

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Episoder(2272)

Shiftheads - Canadians Are Supposed to Buy Canadian - Is the Government Also Following Their Own Program?

Shiftheads - Canadians Are Supposed to Buy Canadian - Is the Government Also Following Their Own Program?

An American company runs the payment portal for an Ontario utility bill. Economist Moshe Lander uses that example to unpack how a business qualifies as Canadian in the first place, and why self-attest...

28 Jul 9min

ICYMI - The Opportunity Says Yes. Your Budget Says Wait.

ICYMI - The Opportunity Says Yes. Your Budget Says Wait.

Surprise expenses show up disguised as good news: a kid making the team, free tickets to a race, a last-minute concert invite. Jessica Moorhouse, author of Everything But Money, unpacks the real cost ...

28 Jul 9min

Can You Really Add a Third Person Into a Relationship?

Can You Really Add a Third Person Into a Relationship?

Before diving into open relationships, the question on the table is simpler: if two people already struggle to make time for each other, how does adding a third person make anything easier? Anyone who...

25 Jul 9min

NEW - It's Technically Illegal to Ship Wine Between Provinces

NEW - It's Technically Illegal to Ship Wine Between Provinces

Provinces claim they're united against tariff threats, but columnist Andrew Caddell points out one premier who can't even agree to loosen alcohol shipping rules without approval from an assembly that ...

25 Jul 9min

ICYMI - Inside Copy: When an MLS Seems to Read His AI Prompt Out Loud in a Real Speech

ICYMI - Inside Copy: When an MLS Seems to Read His AI Prompt Out Loud in a Real Speech

A New Brunswick MLA delivered a speech that still had the AI's own commentary baked into it, proof that the copy button grabs everything, whether you meant to include it or not. Anyone who has ever pa...

25 Jul 9min

SHIFTHEADS: King of the Hill's Best Season Might Be Its Fifteenth

SHIFTHEADS: King of the Hill's Best Season Might Be Its Fifteenth

Steve Stebbing makes the case that King of the Hill's fifteenth season is not just a nostalgic return but genuinely one of the show's best, thanks to real character growth rarely seen in animated sitc...

25 Jul 18min

NEW - The Open Marriage That Fell Apart the Moment It Started

NEW - The Open Marriage That Fell Apart the Moment It Started

A husband spent years pressuring his wife into an open marriage, and the moment she finally agreed and found a boyfriend, he couldn't cope, a real case clinical psychologist Dr. Laurie uses to explain...

25 Jul 17min

Shiftheads - Nobody Can Actually Define AI Adoption

Shiftheads - Nobody Can Actually Define AI Adoption

A government target aims for 60% AI adoption by 2030, and Mohit Rajhans admits the phrase itself is what keeps him up at night, because nobody has actually defined what counts. Anyone who has spent ho...

25 Jul 9min

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