Simon SinekThe Dating Advice Making Us Worse at Love | Relationship Expert Amy Chan
EVERY SPOKEN WORD
50 min read · 9,603 words- 0:00 – 2:26
Why Modern Dating Advice Is Making Us Worse at Love
- SSSimon Sinek
When I look at my favorite couples-
- ACAmy Chan
Yeah
- SSSimon Sinek
... and I, and I have a few of them, like the couples that I like, I want a relationship exactly like theirs. Like, my God.
- ACAmy Chan
Yeah.
- SSSimon Sinek
If I ask any of them, "What's your secret?" They all say the same thing, which is, "We do the work."
- ACAmy Chan
Mm.
- SSSimon Sinek
You know?
- ACAmy Chan
I think what you've explained when you talk about your, 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-
- SSSimon Sinek
Mm
- ACAmy Chan
... and then it'll 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 the hard stuff when you're there for each other, that it goes from good to great.
- SSSimon Sinek
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 peace, 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. [upbeat music] 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.
- 2:26 – 4:12
From Broken Heart to Breakup Bootcamp
- SSSimon Sinek
I'm always fascinated about people's careers-
- ACAmy Chan
Mm
- SSSimon Sinek
... and how we stumble into them, and I think you and I are very similar, that this was not our chosen path.
- ACAmy Chan
No. [laughs]
- SSSimon Sinek
Uh, I never imagined I'd be doing what I'm doing. I don't think you imagined that you'd be an old relationship expert.
- ACAmy Chan
No.
- SSSimon Sinek
You know, you didn't come from this world.
- ACAmy Chan
No.
- SSSimon Sinek
You didn't study it. And, uh, for so many of us who stumble into these things, it's our personal experiences that sort of, you know, the, the solutions we find to the struggles that we're finding. Um, and so you started not by talking about how do people... You started by not trying to help people have relationships, but how to end them, right? Tell me about what happened to you-
- ACAmy Chan
Yeah
- SSSimon Sinek
... that, that unleashed or un- or o- o- opened up an entirely new career, your accidental career.
- ACAmy Chan
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. Um, and then a series of things happened. I lost my job. I moved in with him. And, uh, then, uh, he cheated on me with, uh, a former coworker of mine. Um, and it wasn't just the relationship that fell apart. So much of my identity and future was wrapped up in that relationship that-
- SSSimon Sinek
Like, I am the girlfriend, I'm the wife, I'm the mother. Like-
- ACAmy Chan
I was, yeah, the perfect girlfriend training to be the perfect CEO's wife.
- SSSimon Sinek
Mm.
- ACAmy Chan
Like, that's what I thought was my dream, and that shattered, and I shattered. I... It was dark. Like, it was so hard, and as an achiever, like-
- SSSimon Sinek
Mm
- ACAmy Chan
... there was nothing I could do to get out of that pain.
- SSSimon Sinek
How, how long were you guys together?
- ACAmy Chan
Uh, two years.
- SSSimon Sinek
Okay.
- ACAmy Chan
Yeah. Um,
- 4:12 – 9:50
The Friend Who Changed Everything With One Question
- ACAmy Chan
so I, I just, I really struggled, and, um, when I came out of that, which took quite a long time, like two and a half years-
- SSSimon Sinek
Mm
- ACAmy Chan
... 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." Um, so that's what I did.
- SSSimon Sinek
And what, what, what were the things that you found for you that helped you get out of this malaise for... I mean, two and a half years to be stuck in, in mourning is a long time for any kind of loss-
- ACAmy Chan
For sure
- SSSimon Sinek
... in a relationship or otherwise.
- ACAmy Chan
Yeah. And look, the intensity of the pain, I think, lasted six months. That's when it's, like, constant rumination, revenge plotting. [laughs] Um, but you know, after that, like-
- SSSimon Sinek
Did you... You didn't do anything, did you?
- ACAmy Chan
I didn't, but I had some really good plans.
- SSSimon Sinek
Tell me. I wanna know one of them.
- ACAmy Chan
[laughs]
- SSSimon Sinek
I wanna know one of them.
- ACAmy Chan
Buying bedbugs off the black market and infiltrating her home and his home. [laughs]
- SSSimon Sinek
Wow.
- ACAmy Chan
Wild, right?
- SSSimon Sinek
Oh, no.
- ACAmy Chan
It was bad.
- SSSimon Sinek
But looking back now, you can recognize that if you did that, you're the crazy one, right?
- ACAmy Chan
Yeah.
- SSSimon Sinek
Okay, okay, okay.
- ACAmy Chan
Thank God I didn't do it. Oh my God. [laughs]
- SSSimon Sinek
[laughs] Th- okay, th- this, w- I am fully aware that, you know, this episode, we're gonna be giving advice. This is not the advice part.
- ACAmy Chan
[laughs] Don't do it. Don't do it.
- SSSimon Sinek
[laughs]
- ACAmy Chan
Oh my God.
- SSSimon Sinek
We will not be giving instructions on how to get on the dark web or any links for bedbugs.
- ACAmy Chan
Yeah. So I mean, like, and after a period of time, like, that intense pain went away, but I was resentful, and, like, I was trying to date, but I had a closed heart, and any person I could rally into my corner about what a victim I was and what a villain he was, that would be the story. And it really wasn't until, like- Two and a half years later, I'm having coffee with a friend, catching him up, and I'm, like, telling him the story. I'm like, "What this guy did to me..." And he just stopped me and he's like, "So Amy, does this story serve you?"
- SSSimon Sinek
Mm.
- ACAmy Chan
And I'm like, "No." And he's like, "Oh, can you... Was there any time when he did love you and he was kind?" And I just thought about it. I'm like, "Yeah, there was this and that." And I just realized in that moment, for the last two and a half years, like, all I could see was the dark 'cause that's all I was looking for. And I went home that day and I wrote him a letter of forgiveness, of how I grew, and it was like all those things I was doing that I was like, "This isn't helping," it's like it all came together like glue and it just hit. And I just didn't have any resentment for him after that.
- SSSimon Sinek
What was the impetus for you to s- so you found tools that helped you-
- 9:50 – 11:35
Why Dating Apps Changed How We Think About People
- SSSimon Sinek
Dating seems to be more difficult these days. The... I know young people are later to have sex.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
Young people are... The, the, the, the tenure of relationships seems to be small- shorter.
- ACAmy Chan
Yeah.
- SSSimon Sinek
What is the reason? What i- you've, you've met a lot of people of all ages.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Can you discern that it's a young person challenge, or is it a current day challenge? Like, why does dating feel more difficult than it used to? And I... It's too easy to simply say the internet, you know?
- ACAmy Chan
Right. Yeah. Uh, I think dating apps have changed the way that we meet people, but they change the way we think about people. And if you think about the act of just swiping 100 times a day-
- SSSimon Sinek
Yeah
- ACAmy Chan
... that's what I used to do, just swipe, swipe, swipe, and the 100th person, person I would look at, like, it's just there's so much incoming.
- SSSimon Sinek
It's shopping.
- ACAmy Chan
And we know through research that the things that you're being so picky on for a dating app, um, height, looks, hair, whatever it is, if you met that person at a dinner party, you wouldn't have that same judgment.
- SSSimon Sinek
Yeah.
- ACAmy Chan
But we're meeting people in these ways, and it's changing the way that we see people. So we can even go on a date, have a good date. The second date, we notice they wore flip-flops, and suddenly, if you remember all the stuff you're being fed on Instagram, what an ick. Or maybe they asked you for coffee and not a dinner, and that advice is being told to you, that a coffee, what a waste of your time. So I think that we are walking around with barriers around our heart.
- SSSimon Sinek
Mm.
- ACAmy Chan
We don't trust the media. We don't trust our government. We don't trust thy neighbor.
- SSSimon Sinek
Mm.
- ACAmy Chan
We don't trust anyone. And so how can we connect and see another person as a human being with flaws and have empathy when they mess up when we are doing that?
- SSSimon Sinek
And can that be done with internet dating?
- 11:35 – 13:21
The Skills for Dating vs. The Skills for Relationship
- ACAmy Chan
I think it can be done, but I think that there are certain set of skills we need to learn for dating.
- SSSimon Sinek
Yeah.
- ACAmy Chan
And there are a separate set of skills you need to learn to sustain a relationship. And there are people who are great at dating.
- SSSimon Sinek
Mm.
- ACAmy Chan
They're charismatic. They know what to say. They're adventurous. But those people aren't necessarily good at being a partner.
- SSSimon Sinek
Mm. I, in my experience, what I found fascinating about online dating, and I've done it-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... and I've had success with it-
- ACAmy Chan
Yeah
- SSSimon Sinek
... um, I've also made a lot of friends.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
Um, but what I found really interesting is- Pre-- You know, if you, if you f- if you meet somebody offline, whether it's at a dinner party or a museum or where- wherever it is, the, the initial, uh, connection, there's charm and there's chemistry-
- ACAmy Chan
Yeah
- SSSimon Sinek
... and the sense of humor, and it's after you make the connection you say to the person, "Can I have your number?"
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
And then you go on the first date. But there's already a, there's already a connection before the first date.
- ACAmy Chan
Right.
- SSSimon Sinek
In online dating, the only thing you have is a picture-
- ACAmy Chan
Right
- SSSimon Sinek
... maybe some stats.
- ACAmy Chan
Yeah.
- SSSimon Sinek
But n- usually not even that.
- ACAmy Chan
Yeah.
- SSSimon Sinek
I guess where I'm getting at is it seems like online dating, we're dating things in our imagination. We're holding people up to standards in our imagination.
- ACAmy Chan
Right.
- SSSimon Sinek
And we're getting advice, as you said, you know, people are doing it for clicks and likes, but they're dispensing nonsense very often.
- ACAmy Chan
Right.
- SSSimon Sinek
I'm, I'm so curious if, if this is-- It's clearly not a new experience, but is it exaggerated? Have you noticed-- I wanna know the frustrations you hear from people why their relationships aren't working.
- ACAmy Chan
Yeah. I mean, like, I think in your case w- I, I would imagine for you, people are pro- probably pedestaling you and they have an idea of who you are before they meet
- 13:21 – 14:09
Why Instant Chemistry Can Be a Red Flag
- ACAmy Chan
you. So meeting people online, um, they're not-- They already have, like, almost like a fantasy version. I always advise my clients, "Don't look them up," because you're either gonna pedestal them-
- SSSimon Sinek
Yeah
- ACAmy Chan
... or you're going to judge them.
- SSSimon Sinek
Yeah.
- ACAmy Chan
So, I mean, don't do that-
- SSSimon Sinek
Okay
- ACAmy Chan
... if you can. Um-
- SSSimon Sinek
[laughs]
- ACAmy Chan
But I think there's a lot of other frustrations, and I think they-- there's different ones I hear from women and I hear from men. So I, I feel that the women are saying a lot of the times the guys are talking too much. And I try to explain to them that sometimes s- a guy is talking a lot, s- maybe it's 'cause they're narcissistic, but sometimes it's because they're nervous and they're trying to impress you. And I really advise people, if you felt a connection a five out of 10, if you had a good time, you go again.
- 14:09 – 15:53
The Coffee Date Defense and the "Five Out of Ten Rule"
- ACAmy Chan
I don't think the first date is meant to be like, "Are they gonna be my future baby daddy?"
- SSSimon Sinek
Yeah, yeah, yeah.
- ACAmy Chan
Like, stop that. It makes you future trip.
- SSSimon Sinek
Too much pressure.
- ACAmy Chan
Yeah. It's just a vibe check.
- SSSimon Sinek
Yeah.
- ACAmy Chan
And that is why a coffee is totally okay.
- SSSimon Sinek
Which is, which is like that charming in- interaction at a museum before you go to the first date.
- ACAmy Chan
Yes.
- SSSimon Sinek
You have to treat this like the charming interaction.
- ACAmy Chan
Exactly.
- SSSimon Sinek
That's very good advice.
- ACAmy Chan
And then if that was good, go again.
- SSSimon Sinek
Mm.
- ACAmy Chan
And then it's not until the third date to about 20, I call it the evaluation stage, where you get to know someone and you see, like, is there an alignment of values?
- SSSimon Sinek
Mm.
- ACAmy Chan
Like, those sorts of things. But there are things that you can only tell through experiences with that person.
- SSSimon Sinek
Mm-hmm.
- ACAmy Chan
So I do think it's a great idea to go on that weekend trip, see how they handle stress when something doesn't work out, meet their friends. Before you jump in and be in your mind of like, "I'm committed to th- to this person 'cause they're so great"-
- SSSimon Sinek
Or not
- ACAmy Chan
... allow-- Yeah, allow that time. Um, and I think for some of the guys, like, they're finding that, um, they don't know, like, "Do I, do I kiss them? Do I don't?" Like, they don't know the rules-
- SSSimon Sinek
Mm
- ACAmy Chan
... of engagement anymore. Um, and there's a lot of ghosting going around. So yeah, the behaviors are a lot.
- SSSimon Sinek
Ghosting is-- I mean, like, if you go on one date and it doesn't work out, fine.
- ACAmy Chan
Fine.
- SSSimon Sinek
Don't-- Fine. But I mean, I hear about six-month relationships where somebody just ghosts.
- ACAmy Chan
For sure. It's a lack of ability to deal with conflict.
- SSSimon Sinek
Mm-hmm.
- ACAmy Chan
And it is a reaction that they probably have had since childhood. I think that even with friends, like, looking at these little data points of people who avoid problems. When there's an uncomfortable feeling, instead of having a conversation, they avoid it.
- SSSimon Sinek
Mm.
- 15:53 – 18:13
The Cure for Avoidant Attachment
- SSSimon Sinek
Okay. Is there a cure for avoidance? Asking for a friend.
- ACAmy Chan
Yes, there actually is.
- SSSimon Sinek
Wow.
- ACAmy Chan
So, um, the newer research on attachment-
- SSSimon Sinek
Notice how my body language is completely closing up now.
- ACAmy Chan
[laughs]
- SSSimon Sinek
[laughs]
- ACAmy Chan
So there's newer research on attachment, and that at any given time you're on a spectrum of anxiety and avoidance. So before the idea was like you're in a bucket and that's just where you are.
- SSSimon Sinek
Yeah. Which I've-- Yeah, when I evaluate myself, it's of course complete madness. I, I'm a spectrum of things. I changes. Depends on the person, depends on-
- ACAmy Chan
Right
- SSSimon Sinek
... how much sleep I got. [chuckles]
- ACAmy Chan
Right.
- SSSimon Sinek
I mean, all kinds of things. I can waft in and out-
- ACAmy Chan
Yeah
- SSSimon Sinek
... all the time.
- ACAmy Chan
So if you-
- SSSimon Sinek
I'm glad to hear it's not just me
- ACAmy Chan
... if you date someone-
- SSSimon Sinek
Mm-hmm
- ACAmy Chan
... who has a very full life, right?
- SSSimon Sinek
Mm.
- ACAmy Chan
And, like, their idea of love is, "50% of my love I get from my friends, 50% I get from my romantic relationships," which seems to be more of the world you are in versus a codependent relationship, which is, "100% of my love I get from my romantic partner," that won't do well for you. That will make you run for the hills. But someone who's got their own life going on and then they're, they're not con- constantly at you for more energy, more time, that will probably make you, your nervous system ease in and want them a bit more, right? And so, like, what you wanna do is, like, people who tend to have higher avoidance, they're really good in the first three months, right? 'Cause there's-- You're intoxicated. There's-- The threat of, like, someone getting too close isn't there yet. And usually it's around the three-month mark that something shifts, and what will happen is you'll find an imperfection. There's something that will make this relationship not viable for the long term. Is any of that resonating for your friend?
- SSSimon Sinek
Uh, yeah. Yeah.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Uh, based on the conversations we've had, some of that is true.
- ACAmy Chan
Right.
- SSSimon Sinek
Not all of it.
- ACAmy Chan
Right.
- SSSimon Sinek
But some of it is true, for sure.
- ACAmy Chan
The experiment for a friend who does that is to challenge yourself knowing this is what's going to happen, and it's a very natural reaction where your nervous system is freezing and wanting to run because it doesn't feel safe. And you want to communicate like, "Hey, I'm feeling a little bit flooded," and just try to have that conversation with that secure person and stick it out. Stick it out for another three months. Tolerate the discomfort, and you will move through it-
- 18:13 – 24:49
The ADHD Love Bomb Confession
- SSSimon Sinek
Yeah
- ACAmy Chan
... to deal with it.
- SSSimon Sinek
I did something recently for the first time in my life So 'cause I, I, the ADHD doesn't help, right?
- ACAmy Chan
Right.
- SSSimon Sinek
Because with ADHD I'll fixate on something-
- ACAmy Chan
Yeah
- SSSimon Sinek
... I'll hyperfocus and I'll give- I'll accidentally love bomb somebody-
- ACAmy Chan
Yeah
- SSSimon Sinek
... which can feel great.
- ACAmy Chan
Yeah.
- SSSimon Sinek
You know? And so I'm responsible for giving a ton of energy, and so when they reciprocate, I'm like, "Pressure." But I'm-- They're just reciprocating my energy.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Or the opposite happens with ADHD, which is I meet them, I can't wait to... And then I forget that the-- I forget-
- ACAmy Chan
Mm
- SSSimon Sinek
... to call them. [laughs]
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
Two weeks will go by-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... and be like, "Shit." You know?
- ACAmy Chan
Yeah.
- SSSimon Sinek
But, uh, but what I did something recently for the first time ever, which was lots of high energy, really like each other, going super well. She starts reciprocating with tons of love and energy and attention. I'm like, "Absolutely not. This is not gonna work." I, you know, I was like, "We've only known each other a few weeks and you're trying to lock me down and make me your husband."
- ACAmy Chan
[laughs]
- SSSimon Sinek
"I'm not ready for this." But what I did was... And I literally, she was like texting me every day and sending me pictures-
- ACAmy Chan
What?
- SSSimon Sinek
... and like she's on vacation and she's sending me everything she's doing. I'm like, "I've known you a week." You know? It's like, "I don't need all this," you know? And so I called her up. I said, uh, "I have avoidant tendencies," I said to her.
- ACAmy Chan
Mm.
- SSSimon Sinek
I said, "And so when you give me all this attention, it's pushing me away."
- ACAmy Chan
Right.
- SSSimon Sinek
I said, "You're not doing anything wrong."
- ACAmy Chan
Yeah.
- 24:49 – 25:38
What Self-Care Culture Gets Wrong About Commitment
- SSSimon Sinek
[laughs]
- ACAmy Chan
Anything meaningful in life, building a career, a business from scratch-
- SSSimon Sinek
Yeah
- ACAmy Chan
... a loving, intimate relationship that goes through ups and downs where you're each other's rock, there's not-- There's moments where there's no self-care at all. And for a, a season you just have to, like, suck it up and be committed to the thing that you have com-- like, that you're trying to build. And I think that is a muscle, and I think that is lacking in a younger generation, and that really does worry me. And so when people are wanting to get in a relationship, I think you also have to understand, like, what is their def-definition of commitment and love? Because if they're just about the feelings of being in love, that relationship is going to come to a head between 12 months to 18 months when the love chemicals take a nosedive.
- 25:38 – 27:20
Learning From the Couples Who "Do the Work"
- SSSimon Sinek
Uh, when I, when I look at my favorite couples-
- ACAmy Chan
Yeah
- SSSimon Sinek
... and I, and I have a few of them. I know who they are. Like, the couples that I like-- I want a relationship exactly like theirs. Like, my God. And that, they-- it's not all unicorns and rainbows-
- ACAmy Chan
Yeah
- SSSimon Sinek
... you know, by any stretch of the imagination. But they have dynamics and they have levels of trust, and they have, they've protected each other's independence in ways that I find quite, quite magical.
- ACAmy Chan
Mm.
- SSSimon Sinek
If I ask any of them, "What's your secret?" They all say the same thing, which is, "We do the work."
- ACAmy Chan
Mm.
- SSSimon Sinek
You know? And I think people forget that relationships are effort.
- ACAmy Chan
Yeah.
- SSSimon Sinek
And that, that scares people. Like, "What do you mean I have to do work?"
- ACAmy Chan
Yeah.
- SSSimon Sinek
And what they're forgetting is that if you're on the receiving end of that effort, it feels really good-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... when somebody's willing to do the work for me.
- ACAmy Chan
Yeah.
- SSSimon Sinek
And if it's, if it's mutual, oh my goodness. What a magical thing that somebody's willing to be uncomfortable, sit in discomfort, move through pain, not abandon-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... give second chances, unders- give, uh, uh, uh, benefits of doubt.
- ACAmy Chan
Yeah.
- SSSimon Sinek
You know, all of these things allow personal narratives not to take control of the relationship.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
Um, fight to get to resolution.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Abandon ideas of who's right and who's wrong. All of these things, it feels incredible-
- ACAmy Chan
Yeah
- SSSimon Sinek
... when somebody does it for us. And what I've learned about relationships and what has saved me and made me a better, a better boyfriend is I no longer view relationships as what can I get from a person, but rather what can I give to this person?
- ACAmy Chan
Mm. I think what you've explained when you talk about your, the friends that you have that have great relationships and the ups and downs and the working through it, you describe a great
- 27:20 – 30:31
Meet People Who Are Good Enough, Then Jump In
- ACAmy Chan
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'll be great. It's like as if the perfect person is gonna land on your lap on date two and you're like, "Oh my gosh," like, "This is it." And that's just simply not the case. Like, a great relationship is earned, and it's earned through going up and down and seeing their flaws and that they leave their socks on the floor and it's so annoying but, like, you work through those things. 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 the hard stuff when you're there for each other that it goes from good to great.
- SSSimon Sinek
Mm.
- ACAmy Chan
And I don't think that a lot of people have that mindset.
- SSSimon Sinek
This explains your whole attitude, your whole point of view around dating explains why arranged marriages have a lower divorce rate-
- ACAmy Chan
Yeah
- SSSimon Sinek
... than, than chosen marriages because they show up not because of the swipe-
- ACAmy Chan
Right
- SSSimon Sinek
... but they show up knowing, "Okay, let the work begin." Is that-- I mean, what is your theory as to why arranged marriages do better than, than chosen ones?
- ACAmy Chan
Well, it's, it's commitment and we know like the p- through the paradox of choice when you have so many choices or if you can refund something you'll actually be less satisfied with the thing that you bought. And right now, like we don't have to get married anymore, right? Like I think when we look at our parents' age there were a lot of things or institutions that kept a couple together or you're having family. We know now like it's not taboo to not have a family or to get married. You can cohabitate, you can not. Um, and those things that would keep a relationship together-
- SSSimon Sinek
Mm
- ACAmy Chan
... which will make you go through the uncomfortable times and like I have to abandon my own self-care during the season, we don't have that thing.
- SSSimon Sinek
Mm.
- ACAmy Chan
So why are we together? Just for vibes? And so if the vibe isn't vibing I'm out [laughs] .
- SSSimon Sinek
So much of this is mindset isn't it?
- ACAmy Chan
I think it's mindset and it's like-
- SSSimon Sinek
It's like your attitude towards
- ACAmy Chan
... I, I think it is a maturity of looking at relationships and relationship skills. Um, and you know I have, I had a client, um, a friend yesterday who like wants to be my client and she's like, "Amy like I really-- I, I'm ready to start dating." And she has it in her head that like she needs to date a very, very wealthy person.
- SSSimon Sinek
Mm.
- ACAmy Chan
And I was just trying to like go through and like, "Do you really need that?" And I was like, "You're actually not ready." Uh, and the reason I know that is when someone is ready, actually open for a relationship what they tell me they look for in a partner is not those shiny qualities. They're like-- they're, they're looking at are they kind? How do I feel when I'm with that person? And when someone is just like they need to be this tall, they need to be this age like I'm like you are operating from your ego and that is okay but this is not your season right now to get serious about a relationship because you actually don't want one because your behavior is contradicting what you say you want.
- 30:31 – 33:07
Situationships: The Safe Space That Keeps You Stuck
- SSSimon Sinek
Situationships. I wanna go back to situationships.
- ACAmy Chan
[laughs] Okay.
- SSSimon Sinek
No, no, no, because I think they're pervasive. And in my experience, um, they were girlfriends. We broke up and then never really broke up.
- ACAmy Chan
Okay.
- SSSimon Sinek
Like, we, we were no longer boyfriend/girlfriend. We technically could date whoever else we wanted, but we were just in this sort of limbo, nice space of spending a lot of time together, sleeping over, you know, these lovely situationships that were downgraded from the relationship we had but never re-upgraded. Like, why are they, why are they bad or wrong when, when you have two consenting adults?
- ACAmy Chan
They're not bad or wrong. However, typically what happens is one person wants more.
- SSSimon Sinek
Okay.
- ACAmy Chan
So, and usually they don't know that until the other person finds someone else.
- SSSimon Sinek
Oh, got it. 'Cause, 'cause the situationship is safe. It has all the trappings of a relationship.
- ACAmy Chan
For sure.
- SSSimon Sinek
It has the, the guise of security-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... until one person finds-
- ACAmy Chan
Yeah
- SSSimon Sinek
... someone else to date, and all of a sudden you realize, "Oh my God, I've just been broken up with." [laughs]
- ACAmy Chan
Right. And then you're, you're dealing with the breakup all over again, right?
- SSSimon Sinek
Right. Right.
- ACAmy Chan
'Cause in your body, your body doesn't know that there was a breakup, right? Those neural pathways never had a chance to prune away. And so I work with those clients-
- SSSimon Sinek
Because there was no breakup that happened.
- ACAmy Chan
No.
- SSSimon Sinek
Like, "Babe, we're, we're breaking up," or somebody cheated. It's like they n- they did nothing wrong in finding a partner, a new partner.
- ACAmy Chan
Y- you can't... Like, so there's no transition period from-
- SSSimon Sinek
Yeah, yeah
- ACAmy Chan
... this is romantically over and then we're coming back to it in a different form, right? Your body, they're like, "We've been together this whole time." So when one person in that situation finds someone else-
- SSSimon Sinek
Yeah
- ACAmy Chan
... you're just breaking up like it's square one. And, and there is nothing wrong with it, but you have to also understand, like, if you are doing that and you say you want a relationship, say you want a family, you wanna get married or whatever that is, um, is your heart actually open? Or is that real estate being taken up?
- SSSimon Sinek
Yeah, yeah, of course.
- ACAmy Chan
And we justify, "Oh, no, it's totally fine."
- SSSimon Sinek
Yeah, yeah.
- ACAmy Chan
Yeah.
- 33:07 – 37:24
Leaky Energy and Micro-Cheating
- SSSimon Sinek
what is leaky energy?
- ACAmy Chan
Um, there's two definitions of it. So one leaky energy is when you are just-- maybe you're in a relationship, um, but you're super flirtatious with this person or you're liking people's Instagrams. There's, like, little micro-cheating. You're just getting that validation from a lot of people, and you're not even aware of it. And there's, like, a trail of people in your dust of, like, "Is this person into me or are they not?" And that does have an impact into your primary relationship, even if you think you're being innocent. Um, so that's the definition I operate on for leaky energy, is just being aware of how your energy's coming out and the root of your energy on, like, you could compliment someone, but is that root of that compliment to, like, get validation and to start having some back and forth? Or is that really, like, a generous compliment?
- SSSimon Sinek
I, I wanna unpack this more because there's nothing wrong, especially if you're in a long-term relationship, with finding other people attractive.
- ACAmy Chan
For sure.
- SSSimon Sinek
And you're looking down the street and be like, "Oh, she's cute."
- ACAmy Chan
Yeah.
- SSSimon Sinek
And you know, your girlfriend goes, "Oh, yeah, she is cute," you know?
- ACAmy Chan
Yeah.
- SSSimon Sinek
Like, there's, it's-- there's nothing wrong with that.
- ACAmy Chan
Yeah.
- SSSimon Sinek
You know? There's no intention-
- ACAmy Chan
Yeah
- SSSimon Sinek
... behind it. And so if you're on Instagram just swiping around and, you know, you doomscroll and you, you like something for no reason and you click like and you keep scrolling. And if it's, you know, some girl in a bikini and you click like or some, you know, whatever your it is that you're into and you click like, is that leaky energy?
- ACAmy Chan
So I think it depends because I have clients who are, like, upset that their boyfriend is, like, liking a bunch of Instagram models, right?
- SSSimon Sinek
Right.
- ACAmy Chan
So if that guy is liking all these Instagram models because there is deep down an intention of, like, maybe they'll open up a conversation or DM, that is micro-cheating.
- SSSimon Sinek
Right.
- ACAmy Chan
If that is like, "Oh, cool," like, "I like her yoga pants," whatever it is, and it's genuinely coming from a place of, like, I'm not trying to micro-cheat-
- SSSimon Sinek
Right
- ACAmy Chan
... that's different, right? The same action-
- SSSimon Sinek
How can you tell the difference?
- ACAmy Chan
I think you have to look within yourself. You o- only you know.
- SSSimon Sinek
Hmm. Okay, let's change tacks here.
- ACAmy Chan
[laughs] Okay.
- SSSimon Sinek
Okay. Have you found love?
- ACAmy Chan
I have, yeah.
- SSSimon Sinek
And, uh, how long have you been dating?
- ACAmy Chan
Seven years.
- SSSimon Sinek
Seven years.
- ACAmy Chan
Yeah.
- 37:24 – 40:59
Emotionally Corrective Experiences: How Love Heals Old Wounds
- ACAmy Chan
Yeah. It's a, it's a term used in therapy a lot where, um, it's in relation with another person where you can actually get triggered, and it's an opportunity to almost course correct the old pattern or wound. And so now in a safer environment, you're not a l- you're now not just an eight-year-old adapting and trying to survive, you're with someone who you can trust. So the reaction to behave how you used to can come up, but you can talk to that person. That person isn't going to yell at you or ignore you, and you move through it, and you're like, "Oh, it's actually okay." And the more you do that, that old wound that used to trigger an outsized reaction-
- SSSimon Sinek
Mm
- ACAmy Chan
... starts to get smaller and smaller.
- SSSimon Sinek
It's a process.
- ACAmy Chan
It's a process that happens in relationship.
- SSSimon Sinek
And the, and so that means both parties have to be open to the idea that you won't find the solutions after one infraction, but rather, as you said, the silent treatment gets shorter and shorter and shorter.
- ACAmy Chan
Yeah.
- SSSimon Sinek
What's frustrating about this conversation is it seems like why can't we learn these damn lessons?
- ACAmy Chan
[laughs]
- SSSimon Sinek
It's the same themes. It's, you know, it's learn to communicate.
- ACAmy Chan
Yeah.
- SSSimon Sinek
It's take accountability. It's be, you know, learn how to sit in discomfort. Like, none of this stuff is new. It goes back since, you know, the dawn of relationships. You know, why are we still having this conversation in, you know, 2026?
- ACAmy Chan
I mean, I learned how to dissect frogs when I was in school. I didn't learn how to communicate or use non-violent communication [chuckles] to like express my needs, right? Um, so-
- SSSimon Sinek
Well, now, well, the good news is now you dissect frogs all the time.
- ACAmy Chan
Yes.
- SSSimon Sinek
I mean, that's a, that's a valuable skill.
- ACAmy Chan
Me too. [laughs]
- SSSimon Sinek
You don't need communication in your modern adult life. You need to learn how to dissect frogs. That makes perfect sense to me.
- ACAmy Chan
Yes. Yeah.
- SSSimon Sinek
Yeah. What, with, with all the talks, people you're talking to, what is one of your constant frustrations that no matter how much advice you give, no matter how much guidance you give, s- coaching you give, this problem just keeps rearing its... Like, y- just, it's just a per- a perpetual frustration for you in, in the advice that you give.
- ACAmy Chan
Um, I would say the amount people, of priority people put on, uh, instant chemistry.
- SSSimon Sinek
Mm.
- ACAmy Chan
And this thing that like you're attracted to who you're attracted to and, um, they can be drawn in by someone who has shiny qualities or fits their idea of a type. Um, but we know that through hedonic adaptation we adjust to those things. We adjust to their height. We adjust to their income. We adjust to, I don't know, their waist size. And that thing that drew us in that made us so excited, it goes away-
- SSSimon Sinek
Mm
- ACAmy Chan
... in like two years. So what's left after that? It's the quiet qualities. And research also confirms this. It's the quiet qualities that can, um, predict if a relationship will be happy or successful, and it's how committed is your partner to you? How appreciated do you feel? How well do you handle conflict together? And that might not show up on a second date. Um, and so I think there is... I, I, I'm very optimistic about love. I think that there are a lot of viable partners around us all the time. I think one of our main problems is we have blinders on because we are overemphasizing the things that don't matter in the long term.
- SSSimon Sinek
But it's easier said than done, right? I'm listening to you, I'm going, "Yep, yep, yep." But how do we change our mindset to not focus on those things, look past those things in a world that is bombarding us-
- ACAmy Chan
Yeah
- SSSimon Sinek
... with those things?
- 40:59 – 44:41
The Nine-Person Dating Experiment
- ACAmy Chan
Yeah. Um, I make my clients go on a dating experiment where they have to date nine different people totally outside of their type. Because then I tell someone, "Change your type." Illogically, maybe go through one ear, go, go out the other. But if I'm like, okay, I have a client who has like a six-foot height requirement, one of the people they have to date is someone short, shorter than them, right? I'll have a, a client who's like, "I only date people 25 to 29." I'll have them date someone older than them. And the way they do this experiment is they can't get into a relationship with any of them. So it changes the way that they date because there isn't that pressure of finding the one. They're just like, "I'm just doing this experiment." And at the end of the nine people, you can look at who was the best in terms of your benchmark, right? You can go back to that person, or you now know in your future dates who you're looking, what type you're looking for.
- SSSimon Sinek
Is that communicated to these nine people? 'Cause it's a little mean to go and date-
- ACAmy Chan
It's, it's, it's not communicated until it goes a little bit deeper.
- SSSimon Sinek
Okay.
- ACAmy Chan
And then someone will say something.
- SSSimon Sinek
Okay. 'Cause it's a little bit mean to set up expectations like, "I'm on an experiment date, but you're gonna fall in love with me."
- ACAmy Chan
[laughs] Well, no, but here's what happens, right?
- SSSimon Sinek
[laughs]
- ACAmy Chan
So a, a lot of the people who finish this end up getting in a relationship. They don't finish it. Um, and they say the exact same thing to me. They're like, "Amy, I'm with someone I would have never given a chance to." And it is human beings, we're drawn to what's familiar.
- SSSimon Sinek
Yeah.
- ACAmy Chan
So if you are familiar with the guy who's just a little bit unattainable, um, you're constantly going to be attracting and being drawn to that emotional experience.
- SSSimon Sinek
Yeah.
- ACAmy Chan
So I'm-- the experiment makes you be in situations where, oh, like I'm now prioritizing kindness and other things I never did before, and you get familiar with how that feels like.
- SSSimon Sinek
I know why a lot of my relationships for many years failed. I had a bad picker.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
I would date the wrong kind of person over and over-
- ACAmy Chan
Yeah
- SSSimon Sinek
... and over again. And, uh, and, uh, for various reasons.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Um, but I, I recognized that I had a bad picker, that, uh, that I-- they're good people-
- ACAmy Chan
Mm-hmm
- SSSimon Sinek
... but they're not for me, you know, and I'm not for them. But I kept finding myself dating very similar personality profiles over and over and over again.
- ACAmy Chan
Yeah.
- SSSimon Sinek
And it was a big deal for me to recognize that, and it's hard to break.
- ACAmy Chan
Yeah.
- SSSimon Sinek
It's very hard to break.
- ACAmy Chan
Yeah.
- SSSimon Sinek
I really like talking to you. Like, you know, because I can't help but filter everything you're saying through my own experience, of course. And I'm soaking as much as I can. Um, I, I-- there's a, there's-- It, it-- maybe it's just because it's broadcast on, on, on Instagram and on, on TikTok, but there seems to be more skews younger, but it's-- I think that's just 'cause they're broadcasting on [chuckles] Instagram and TikTok. All, all the people just aren't broadcasting their experiences as much. But there seems to be more people who don't know how to date. Forget about being in the relationship. There's one person that I follow on Instagram whose, whose content I love, and she's, she's super affirmative and, like, like, just great a-advice giver, just, just a good, good, kind heart who spreads a lot of positivity, which is what I like. And every now and then she'll post a video how she, she's never had a boyfriend.
- ACAmy Chan
Mm.
- SSSimon Sinek
She barely dates. But young, attractive, successful, you know? Doing well in her, in her online influencer [chuckles] life.
- 44:41 – 45:49
Why Young People Aren't Dating Anymore
- SSSimon Sinek
common. I'm meeting people in their 20s who've never really had more than a couple of dates here and there.
- ACAmy Chan
Yeah.
- SSSimon Sinek
W-what's going on?
- ACAmy Chan
Uh-
- SSSimon Sinek
And, and, and I'm asking for the people who are listening who are young, but also for the parents of, of young people.
- ACAmy Chan
Yeah. Um, a lot of social skills have atrophied. Some of that is due to the pandemic. A lot of that is anxiety. And so the idea of going out in the wild at a coffee shop and approaching someone and risking rejection or someone not interested in you, there's so much anxiety of doing that, so why would I bother? I would rather just doom scroll, or I'll do this other thing that will give me a hit of dopamine. And you do that enough times, and then you just don't ever do that thing of meeting someone in person or having the conversation. And again, I do think this is-- there's a message that we need to avoid the uncomfortable feelings.
- SSSimon Sinek
Yeah.
- ACAmy Chan
And bad feelings equals bad. And so they're not. You can get rejected and it's okay. [laughs]
- 45:49 – 47:03
Bad Feelings Don't Mean It's Bad
- SSSimon Sinek
Let's double-click on that.
- ACAmy Chan
[gasps]
- SSSimon Sinek
Let's double-click on that. That is so good. Bad feelings does not mean it's bad.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Right. Uncomfortable doesn't mean narcissistic or toxic.
- ACAmy Chan
No.
- SSSimon Sinek
It just means uncomfortable.
- ACAmy Chan
Yeah.
- SSSimon Sinek
All the advice that we're getting is about mitigating, blaming, letting ourselves off the hook, and very few people are giving us advice to enjoy, and I mean enjoy, discomfort, anger, depression. Um, depression is only a bad thing if you get stuck in it.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
If it's capital D depression, that's a medical condition.
- ACAmy Chan
Mm-hmm.
- SSSimon Sinek
Um, it's perfectly normal and healthy to be sad.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Uh, that it's part of being human to be messy, and you can't be happy every day. And I think the thing that I've learned as I've grown older, which is I, I saw negative feelings, bad feelings as somehow making me weaker.
- ACAmy Chan
Mm.
- SSSimon Sinek
And that if I was happy and, and optimistic all the time, that makes me stronger. And what I've learned is, no, what makes me a great human being is that I have a range of emotions.
- ACAmy Chan
Right.
- SSSimon Sinek
I, I learned this in a funny way. Um,
- 47:03 – 48:02
The Dead Bird and the Range of Emotions
- SSSimon Sinek
I'm an art collector. I collect a lot of art, as you may m- see. There's a ton of it. And I bought a sketch of a dead bird. [clears throat] And it showed up in the mail, and I unscrolled it. You know, it was all rolled up in the tube, and I unrolled it, and I had instant buyer's remorse.
- ACAmy Chan
Oh.
- SSSimon Sinek
Like, what the hell do I want with a picture of a dead bird for? Like, I'm not gonna hang a dead bird on my wall. You gotta be kidding me.
- ACAmy Chan
[laughs]
- SSSimon Sinek
And I was like, "What have I done?" Like, "Why did I buy this?" You know? And by sheer luck, I had a friend over when the mail arrived who's an artist. And I'm, I'm, I'm s- expressing all my buyer's remorse, and she looks at me and she goes, "A good art collection has a range of emotions."
- ACAmy Chan
Oof.
- SSSimon Sinek
And in that moment, I fell in love with my dead bird, had it framed, and it hangs very proudly on my wall.
- ACAmy Chan
[laughs]
- SSSimon Sinek
Because my art collection has a range of emotions, and this is what I've learned about great human beings.
- ACAmy Chan
Yeah.
- SSSimon Sinek
You're getting me thinking. I'm connecting a lot of dots and seeing all these
- 48:02 – 50:00
The Two Skills That Save Every Relationship
- SSSimon Sinek
connections, but what I'm taking away from this entire conversation with you is the skill, the single skill that we all have to learn in order to succeed in dating and to succeed in relationships is our ability to sit in discomfort. And the single best way to manage discomfort is to learn how to communicate.
- ACAmy Chan
Yeah.
- SSSimon Sinek
That's my takeaway.
- ACAmy Chan
And I'll add on top of that, is to be aware of the story you're reinforcing.
- SSSimon Sinek
Uh, uh, yes. The reframing and the mindset. Yes.
- ACAmy Chan
'Cause whatever you keep repeating, right? You go and you approach someone at the coffee shop, or you DM and you get rejected, and then suddenly it is, "Oh, dating sucks in LA."
- SSSimon Sinek
Yeah.
- ACAmy Chan
Right? Or, "These people are like this."
- SSSimon Sinek
Yeah.
- ACAmy Chan
And you keep saying it over and over again. Or, "I'm an avoidant. Ugh, I'm always such an avoidant in relationships." Um, that becomes your narrative-
- SSSimon Sinek
Yeah. Yeah, yeah, yeah
- ACAmy Chan
... and your identity and your future.
- SSSimon Sinek
A really good, really good-- Not, "I am an avoidant," or, "I have avoidant or anxious attachment," but r- it's not a diagnosis, for heaven's sakes.
- ACAmy Chan
Exactly.
- SSSimon Sinek
It's a, it's, "I have had avoidant tendencies."
- ACAmy Chan
Yeah. Yeah.
- SSSimon Sinek
And, uh, I, I like that it's, you know, "I have had avoidant tendencies," which is, it's a past pattern.
- ACAmy Chan
Right.
- SSSimon Sinek
It's not who I am.
- ACAmy Chan
Exactly. Yeah.
- SSSimon Sinek
Yeah, yeah, yeah. It's not a predetermined... It's not a, it's not predestiny.
- ACAmy Chan
Yeah.
- SSSimon Sinek
Predestined.
- ACAmy Chan
Yeah.
- SSSimon Sinek
You're really good at what you do.
- ACAmy Chan
[chuckles] Thank you.
- SSSimon Sinek
Good stuff.
- ACAmy Chan
[laughs]
- SSSimon Sinek
Amy, thanks so much for coming on.
- ACAmy Chan
Thanks for having me.
Episode duration: 50:00
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