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The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan artwork

The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan

A Bit of Optimism

September 15, 2026

The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle. It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now.

Speakers Simon Sinek, Amy Chan, David Robinson

TopicsCareersBusinessEducationSelf-Improvement

Simon Sinek (0:00)

When I look at my favorite couples, and I have a few of them, like the couples that I like, I want a relationship exactly like theirs. Like, my god.

If I ask any of them, what's your secret? They all say the same thing, which is, we do the work, you know?

Amy Chan (0:15)

I think what you've explained when you talk about the friends that you have that have great relationships, and the ups and downs and the working through it, you describe a great relationship. And I think a challenge that people have today is this mindset that they need to meet the perfect person first, and then it will be great. We need to meet people who are good enough, and then we jump in with two feet, and then through going through the stuff, it's a hard stuff when you're there for each other, that it goes from good to great.

Simon Sinek (0:48)

Some of the dating advice that we follow might actually be making us worse at dating. Know your type, trust the spark, watch for red flags, never settle, protect your piece, and if someone isn't quite right, there are hundreds of other options waiting on an app. The problem is the person who's great on a first date isn't necessarily great at a relationship. Instant chemistry isn't a good sign. A red flag might just be an imperfection, and keeping our options open can make us pretty terrible at actually choosing someone. That's why I wanted to talk to Amy Chan. For nearly two decades, she looks at dating through a sort of psychology and neuroscience lens. Why we're attracted to certain people and why relationships fall apart. She's also the founder of Renew Breakup Bootcamp and the author of Unsingle. Her work makes the case that finding love isn't just about finding the right person. It's about getting better at the skills love requires. It turns out dating takes practice, and so does staying in love.

If you like what you hear, please remember to subscribe. This is A Bit of Optimism.

This episode is proudly brought to you by SAP.

Building trusting relationships with clients, it turns out, takes more than simply being an expert in your client's business. It actually is about empathy and being willing to step outside your own comfort zone. To learn more about SAP, the AI Cloud ERP for businesses of all size, head to sap.com/grow. I'm always fascinated about people's careers and how we stumble into them. I think you and I are very similar that this was not our chosen path.

David Robinson (2:34)

No.

Simon Sinek (2:35)

I never imagined I'd be doing what I'm doing. I don't think you imagine that you'd be an old relationship expert.

David Robinson (2:39)

No.

Simon Sinek (2:39)

You didn't come from this world. You didn't study it.

For so many of us who stumble into these things, it's our personal experiences that sort of, you know, the solutions we find are the struggles that we're finding. And so you started not by talking about how to people, you started by not trying to help people have relationships, but how to end them, right? Tell me about what happened to you that unleashed or opened up an entirely new career, your accidental career.

Amy Chan (3:09)

Yeah. So I was in a relationship in Vancouver and I thought I was living the dream. And back then living the dream meant you date to get married and then you have children. And then the plan I had with this guy who ran a business was I would write on the side for fun and we would have kids and everything was set. And then a series of things happened. I lost my job. I moved in with him. And then he cheated on me with a former coworker of mine.

And it wasn't just a relationship that fell apart. So much of my identity and future was wrapped up in that relationship.

Simon Sinek (3:47)

Like, I am the girlfriend. I'm the wife. I'm the mother.

Amy Chan (3:50)

I was, yeah, the perfect girlfriend training to be the perfect CEO's wife. Like, that's what I thought was my dream and that shattered and I shattered.

It was dark. Like, it was so hard and as an achiever, like, there was nothing I could do to get out of that pain.

Simon Sinek (4:07)

How long were you guys together?

Amy Chan (4:08)

Two years. Okay. Yeah.

So, I just, I really struggled and when I came out of that, which took quite a long time, like two and a half years, I was like, what happens to those people who don't have friends that will lend them a couch or know what books to read or have a therapist? So, I was like, I have to create what didn't exist for me. So, that's what I did.

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