Innovating Our Relationship

Technology has impacted our partnership more than we ever imagined.

The Cave Project

and

Greg Swan

Jun 01, 2025

Transcript

We got married at 23. Now we’re on our fifth marriage—to each other. And that’s thanks to technology.

This week’s episode is raw, hilarious, deeply personal, and maybe our most important one yet. It’s about relationship innovation. Not startups, not tech, but something far more complicated: long-term love.

Jenny and Greg Swan go all-in on what it looks like to renegotiate your partnership… while still being in it. From high school marching band zings to 500,000+ miles of business travel, stay-at-home parenting to career rebirth, this episode covers how technology, therapy, and shared Google Calendars can literally save a relationship. Or reinvent it.

We’re not talking about “making it work.” We’re talking about redesigning it to work better. The secret? Letting go of old agreements, rebalancing the roles, and trusting that the person you married at 23 might be someone totally new at 45. That’s not a problem. It’s the point.

Here’s what’s inside:

What it means to have multiple marriages with the same person (Esther Perel, we see you).
Why Jenny told Greg, “I don’t want to be married to the ad guy anymore.”
How COVID accidentally gave us the clarity—and courage—to completely flip the script.
The underrated power of shared calendars and telehealth and viewing technology as added-value for a foundational partnership.
And yes, the origin story of the Sip-and-Sax™ (pending trademark). 🎷🥤

👀 Quotable Quotes

“The secret of change is to focus all your energy not on fighting the old, but on building the new.” – Socrates
“Most of us will have 2 or 3 marriages in this life. And if we're lucky, they're with the same person.” - Esther Perel

This isn’t a rom-com. And this isn’t an anti-divorce episode. This is what happens when two very real people use all the tools to build a better, more equitable partnership.

So, go listen. If you’ve ever felt like something needed to shift in your relationship, but weren’t sure how to say it, this episode’s for you.

🎧 Listen to “Innovating Our Relationship” now:

🎙️ Check out The Cave Project Archives

If you’re just joining us, welcome! We’re on Season 2 of The Cave Project — a movement exploring the nuance of our modern-day reality and the tension of our technological future with Jenny and Greg Swan. Learn more about us here. Check out the archives here.