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I sit down with Ed, a Berkeley and Stanford trained engineer who had a startup exit ($8 Billion project), retired early, and is now rebuilding love after a long marriage while staying on great terms with his ex-wife. He is thoughtful, active, and honest about what it is like to re-enter online dating in midlife with real intention.

We get into the stuff people usually avoid: when chemistry turns physical fast, how sex boundaries can protect trust, and why rushing into sex often clouds judgment for both men and women. We also talk about the modern breakup problem, ghosting and ending relationships through text, and how conflict avoidance shows up as avoidant attachment behaviors. We discuss self-awareness, the perfect label, anxious attachment and communications.

Ed also shares the most surprising tools he is using right now: an AI dating coach and an attachment-focused AI journaling app that helped him uncover deeper patterns through Internal Family Systems style prompts.

We close with practical relationship advice. If you want more clarity in dating after divorce, better communication, and stronger emotional intelligence, you will get a lot from this conversation.

Resources:

📗 Eight Dates by John Gottman

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Today, I am joined by Dara Rahill, a former top-ranked premium matchmaker at the country's largest matchmaking platform, and now the founder of Dara Rae Matchmaking, to reveal what actually predicts a healthy long-term relationship when you look beyond photos, height filters, and perfect-on-paper stats.

We dig into the behind-the-scenes reality of modern dating: “checklists”, dating profiles, and how dating app culture amplifies snap judgments.

Dara explains how real compatibility is assessed, plus the intuitive “art” a matchmaker develops after interviewing thousands of singles. We also unpack why even highly sought-after people sometimes choose high-end matchmaking services.

One of the most eye-opening parts is who can be hardest to match and why. We also challenge the myth of instant chemistry, exploring how attraction can grow through repeated exposure.

If you’re tired of guessing, lower-stakes clarity starts here. Great episode for both men and women.

🎀 Dara Rae Matchmaking

🫶 Dara Rae Instagram

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Dating a Bay Area engineer can look perfect on paper… but feel unexpectedly lonely in real life.

In this episode, we get brutally honest about what it’s actually like dating engineers in Silicon Valley—the parts that feel safe and stable, and the parts that quietly hurt. Violina is back, and we’re sharing real stories, unpacking patterns we kept running into, and reflecting on the moments that led to some big realizations.

We also talk about the green flags—what draws so many people to engineers in the first place—and why those same traits can sometimes create disconnect in relationships.

This is about understanding what works, what doesn’t, and what actually matters in the long run. If you’ve ever felt like you’re dating someone who tries to debug emotions instead of actually feeling them, this conversation will hit home.

Whether you’re dating in the Bay Area, seeing a software engineer, or you are an engineer wanting to understand how this dynamic can land, this episode offers clarity—and some practical questions you’ll wish you had asked earlier.

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