Dating 101 as an Ambitious Woman: How to Seduce Anyone (ft. Chloe Shih)

You telling me this is your first time going on a date with a woman?

Chloe Shee is a Forbes 30 Under 30 content creator and the host of the podcast The Joy of Missing Out. How did you meet your husband?

I was like fighting for my life all my 20s. Then I met him and I was like, why don't you have trauma and problems?

Today we're going to hear her top lessons and craziest relationship stories.

There's 4 things that have a 90% predictability of whether your marriage is going to fail. And number 1 is— I'm Chloe Shee and this is The Burnouts.

Chloe, I'm so excited to have you here. Thank you so much for coming on The Burnouts.

What do you think have been things that you've done that have contributed to the success of your relationship?

I think something that's really important, especially because like Kevin's never dated before and I don't want a mother, is, uh, we went to do— we, we, we started couples therapy probably like 9 months into the relationship. And I think what a lot of guys have trouble with is articulating their feelings because they always have to be like right and sure before they express. So we, we started couples therapy and we still do it today. And it's been the best thing ever. Like I think couples therapy is the biggest life hack because again, your partner is the most important decision of your life. But why, why do people do it blind? Like why do people just go and they pick and then they don't get any help? Like we get teachers, we get tutors, we get, we get, we get coaches for, for personal training, but we don't have someone to help with our biggest decision in life. Um, and also people who seek couples therapy, they're— I think that— I think like either 60% or 90% of couples, their communication improves, uh, their children are less traumatized, they're more emotionally stable, and, um, you learn how to fight really well. And I just think that there's a lot to gain with a little to give. And so like, why not? But there's so much— people think, oh, you have a problem if you go through couples therapy. And actually I think, I think Dr. John Gottman, the relationship psychologist, I think researcher, says that it unhappy couples, they, they spend about like 6 years before they seek couples therapy. And imagine all the resentment that builds across 6 years that you cannot easily reverse through just talking. So we started from the beginning and it's, it's been awesome. We learn how to turn towards each other. We learn how to be like, it's not you versus me, it's us versus the problem. Uh, we learn how to talk when things are vague and be and share hard conversations, because it's never a good time to, to talk about hard conversations. It never is. Yeah.

And how do you know when you have like the right couples therapist?

I've only ever had one, so actually mine is an Asian man. And I think it was important because Kevin was kind of like against therapy before because he, he was not as in touch with his emotions as the women are. And I was like already going through my own personal therapy, so I was like, yeah, hell yeah. But I think he needed to see an Asian man because it's not something that Asian men really do, to, to see it modeled. Oh wow. Yeah, and I think that was powerful to him because if he saw someone else and he won't relate and realize like, oh, this is for me too.

I love that. I mean, it's really interesting because there's been a lot of studies about how having good relationships in your life can be one of the biggest contributors to wealth, to happiness, and it's something that is often really not talked about, especially when we talk about career.

Yeah. I agree. So my inner peace is through the roof. I was like, I didn't know life could be like this. I was like fighting for my life all my 20s. Then I met him and I was like, why don't you have trauma and problems? And he's like, I don't know, it's— life's not that deep. And you know, life's good. Yeah, your life is good. Your life is good, Chloe. You have enough.

What would you say the biggest takeaway from your couple counseling with Kevin has been?

100%, it is learning how to fight well. And I think that that's how like most marriages fail. Like, I think I went on this journey of researching and reading about how marriage works, how marriage fails, because I don't want to get a divorce. Like, I don't be part of that 50%, 55% statistic. So, um, I read that there is a concept called the Four Horsemen of the Marriage Apocalypse by Dr. John Gottman. Is there's four things that have a 90% of predictability of whether your marriage is going to fail. And number one is if you see a couple criticizing each other, so attacking your character, not your behavior. That sucks. The second is contempt, so you are disrespecting them or making jabs at them or belittling them. Like, you know how people make snide remarks like, oh, like, you look a little chubby today, or like, you're not that smart, like, haha, she's not that smart. Like, those moments really build up resentment and fester, and you— they're not big enough in the moment to call out, but you like remember them in your subconscious. The third is defensiveness, like you shift blame, you never take up blame, you always like think being right is more important than the other person's feelings. And last one is stonewalling, is when you shut down when you're having a hard time and you just, just like, you just shut down. And I've seen that happen a lot. Like, the rest are kind of easier to address, I think, but stonewalling is pretty tough for the relationships that I've seen. And because it's like a, it's like a physical response, and you like shut down, you can't communicate, and you sometimes you run away, sometimes you just say nothing. And that's not coming in. So I think learning about, oh, if we can solve and, and learn our muscles around these 4 problems, then I think we can solve a lot of issues. Um, yeah. And I think that couples therapy is really important for even when times are good, because when times are good, you can go into future planning. And then in every area of your life, the times when you divorce are when you're going through big life milestones— when you move, when you get a new job, when you get married, when you get kids, when you buy a house, when you have to merge finances. And those don't happen all at once. Sometimes they do. That's crazy. But they happen in different stages of your life and there are always new problems to address and you become a different person. So how do you grow together during different seasons of life? And, uh, yeah, that's— I— couples therapy, I support it.

I love this because selfishly I'm applying it back to also even beyond like my romantic relationship, like our relationship of like conflict always happens when you're going through big things with the company of, okay, do we need to let someone go? We're raising a huge round, or okay, we're launching this thing. And so I think all of these, I mean, I'm guilty of many of the things that that you've just named have been huge for our relationship of figuring out, like, when you're co-founders, you're going to have conflict all the time. How do we do that actually productively? Most of the time when we have conflict, it's because neither of us know the right answer about, okay, what do we need to do here? Okay, maybe we need to go get a mentor and bring that in. But I love this. So maybe next time we're going to be bringing on your couples therapist.

Oh my God, I didn't even sign you up.

Oh my God.

Oh, I thought—

oh.

Wait, and for people who aren't at the stage yet where they're married or they haven't found a partner, tell us about the art of seduction and flirting.

What I have learned is, um, have a good wager, have a good bet, you know, like be a little playful, like, uh, let's play, like, let's wager, or if you win, if you win at this, then I'll buy you ice cream, or like something that has risk and a reward. I think that's really fun and playful because then you're always like on the edge and there's something to there's an objective. But I also think it comes down to like knowing your, your, what your charm is, what your inner, inner charm. There's a superficial charm and your inner charm and who you are at the beginning versus who you are deep down. That's really charming.

How did you meet your husband and kind of like what role has he played as you've navigated your career?

I met him in San Francisco. He was an engineer at Twitch and I just had friends that worked at Twitch. So I met him through mutual friends at events. Be like, hey, you want to come to my thing? My co-workers are there. And then I met him there and he wanted to say what's up. And I was like, ew, please don't talk to me, I'm trying to hustle. And what? And then he just kept saying hi. And I was like— he was like, oh, do you want to come to Twitch happy hour? And I was like, no. Um, and I think one day I had to be at Twitch for like a PM thing, and then my host was like stuck in meetings. I was like, huh, I wonder who's here that can help me. Oh yeah, he's there, his name's Kevin. I was like, oh Kevin, are around? And obviously he's like not doing anything because he's an engineer and he's in meetings. He's like, yeah, of course. And he comes down to the game room and he brings like a group of boys and they're like playing Smash Melee in the game room at Twitch. And I'm like, it's 11 AM, how do you guys not have meetings? Like, it's so confusing. But yeah, that's the beginning. And then I think we went to a party, like a birth— someone's birthday party. We kind of hung out. And the next day he shot his shot and just texted me saying, I know you hate it when people like debate you and and like want to hang out with you, but they make it a date without telling you. So I just want to say I think you're really cool. I'd love to take you on a date if you're open to it. Yeah. And I was like, you know what, that takes guts. It takes guts to say, say the word date. And yeah, uh, yeah, sure, why not. And it was a horrible first date, but it worked out.

Why was it horrible?

Um, because it was his first time. He was his first— okay, so Yeah, he didn't have a lot of experience. And we went to like the dessert place, and then I was like, you know, I was like, so, uh, so, so what are you looking for in a romantic relationship? And he was like, huh? And then I'm like, what do you mean, huh? He's like, um, no one's ever asked me that before. Uh, and then I'm like, oh, what do you mean no one's ever asked you? Like, surely you've talked about it, right? Like, surely you've talked about—

your mother's never asked you?

Yeah, like, what? And he's like, no, I've never— I've never done this before. And I'm like, never done what? It's like, I'm never dated before. I'm like, you mean you've never had a girlfriend before? And he's like, no, I've never gone on a date before. And I'm like, you telling me this is your first time going on a date with a woman? And he was like, yeah. And I'm like, were you his first kiss? Yes, first everything, first everything. Yeah, wait, he seems so sweet.

Yeah, he's a sweetie. What's your take on that? Because I feel like a lot of people Yeah, love it.

For sure. I felt that. I felt that. I was like, I'm gonna be a mother. I'm gonna be a mother again. A mother of a child. Um, no one likes being a mother. I don't— I, I don't think, you know, mothering your partner is like a lot. But, um, yeah, that's why I hesitated a lot. So then I was like, oh, maybe, you know what, it's fine, don't worry about it. Like, maybe I can ask you another question. Uh, what about friends? Like, you have friends. Uh, what do you look for in friendship? And then I can see a sweat gland coming from the top of his forehead, just coming down. He's like, uh, uh, and he takes a napkin, just pats it. And then I'm like— he's like, no one's ever asked me that too. And I'm like, oh my God, all right, you know what, you have a job, I have a job, what are your career goals? And he was like, I don't have any. And I'm like, oh my God, oh no, oh no, how do I— I don't— but I don't want to— I don't want to like walk away, you know. I think it's 49ers, right? The 49ers. You know the 49ers thing?

The football?

No, what is that?

Um, in the Bay Area, uh, girls are called 49ers— 4s who think they're 9s— because of the ratio. So they treat men really poorly, and it traumatized a lot of men. And then guys go into this like weird route of like, like, you know, path. And so I didn't want to traumatize another like fresh guy, so I was like, okay, you know what, we're gonna have a great first date. So I just start asking him all kinds of questions about his life. We go to Twin Peaks. Week, we go to a tiki bar. And then at the end I was like, yeah, I don't think— I think we're in different stages of our lives and we're looking for different things. I don't think it's gonna work out.

Did you say it like this?

No, it was a little bit more serious. Yeah, face to face, it was a little more serious.

How did he react?

He was pretty sad. He knew he messed up. He knew like he just like wrecked it. But he was just— he's grateful regardless. He's a Midwestern man, a very grateful man.

Wait, so how did it— how did the spark come back? Or lack of spark, how did it get ignited?

You're like trying to interpret— you're trying to understand this. Um, so I think what happened was because he got rejected, he realized like he has nothing to lose anymore. He, uh, sent a message follow-up like, oh, I had— I thought about this a little deeper and here's my answer on friendship and my career. And the reason, um, he had no career goals is he's not someone who's like very, these are my must-have career goals. He's already really successful. He's a software engineer. He already got promoted like earlier than I did. He made more money than I did and Um, he's really smart. He went to UMich. He's like a very smart cookie.

And we love UMich.

Yeah, it's great.

If you go to UMich, the applications are open. He have friends, tell them to apply. Anyways, continue.

And then, um, and I think that if he wanted to do something, he'll just do it. He doesn't, he like has so many interests and then I don't think he wants to be like a CEO of a tech company. I think a lot of people wanted to do that. So it's not that he's not ambitious, it's that he doesn't have career goals in the way that Silicon Valley people. Okay.

Okay.

But what did he say about what he wanted in a relationship? When he thought deeper?

Oh, not much. Yeah, no, that, that he didn't address that part because it was his first time. He was like, uh, I thought, I thought a date was like just people chatting. Like, this is an interview now. I have no clue. So we had to discover that over time. That was, that was probably a hard thing.

But you agreed to go on a second date with him?

Um, what happened was he started— we started messaging and he was just super funny. Yeah, he's a funny dude. And I found myself just laughing so hard at my messages. And when do we laugh at messages anymore? So to be excited about a message and laugh was really amazing. Uh, but it's a really long story, but essentially over the course of 6 months, we try to go on dates again. But then I also, I always felt hesitant because I was like, this is not, this is not what I wanted on my list. We all have a list, a list of who we want in our partner, and I have 25 things and you got none of them. So why am I doing this? But I had such a good time with him and he was so supportive and I was going through a new job. That was when I was like, just joined Facebook, and he was really supportive of like, uh, he would help. I remember he would like teach me how to code and then help me with SQL because I was like trying to build dashboards.

Oh God, not SQL. Give me— bring up my PTSD. I hate SQL.

Yeah, I mean, it's awesome to have someone support you through your low times. Um, and then I was supposed to go to the Facebook holiday party when we had holiday parties. Yo, that was a time of life. It was adult prom. Like, I think that's like what's missing in this day and age— adult proms. But, uh, holiday company holiday party at book was a banger. It was like Game of Thrones themed. But I only could be there for an hour because I had to go to Tahoe after. So I was like, who in my friend group would be down to be my plus one for just an hour? Oh, Kevin! So then he's like, yeah, sure.

So you considered him a friend? Yeah. Oh, okay.

Did you tell me in jail? Put me in jail!

No, no, I am—

you are—

you were Kevin.

Yeah, you, you were so patient with Kevin. This is a beautiful story. So you invited Kevin as friend.

Yeah, as my friend.

No, I think that the story here is that Kevin is the, the re— like, the rebound king. What is it called when you come back from nothing?

Redemption.

Redemption.

He's the redemption king. Like, I mean, this guy started with saying he had no career goals, no friends, no girlfriend, and then he went from the friend to husband pipeline because of his humor and kindness. Kevin must be the kindest, funniest guy alive. I'm loving Kevin right now, and it sounds like he's a genius. I'm, I'm very big Kevin fan.

Yeah, we are all Kevin fans. Like, me and my girlfriends, we all love Kevin. Kevin's like the, the greenest flag.

Is Kevin now like the guy in the friend group who's able to give everyone relationship advice?

And it's the funniest thing ever because he has no relationship experience. Even when before me, all the girls would go to him and be like, what do you think of this? And Kevin's like, well, here's my take, but also know that I don't have any experience. Wow.

And so tell us, so you guys go to this— oh yes, Facebook prom together.

We go to Facebook prom together, and then he We're like going on the dance floor and the man starts busting out and like, uh, just breakdancing. And I'm like, huh, who is this software engineer, dual monitor, mechanical keyboard, RGB loving, Melee playing guy?

And were you like, woo?

Yeah. I was like, and he's breakdancing. Yeah. Man is breakdancing in his suit and I'm like, something's in the air. And then, and of course he's like a little lit. He's a little lit for sure. And then Kevin, I have a friend who's gonna stay at my place. A lot of people in South Bay, you know, they'll like crash in San Francisco. Live in San Francisco. So he— I'm supposed to take him to my place. And so Kevin afterwards, putting Kevin on blast, Kevin, um, was like, all right, you better listen up because I'm only gonna say this once. And imagine, green flag puppy, like kindest, sweetest guy. Ditch the other guy and come home with me tonight. And I was like, I look at the other guy, I look at Kevin, I'm like, bruh, to the other guy, take my keys. I'll see you tomorrow. And then I go with Kevin and then, uh, we have a great night. And then I go on a business trip to like Europe or something. And I reflect hard on my life and I write down those 25 things I'm looking for in a partner. And I come back and I'm like, Kevin, I'm ready to commit to you, but here are my 25 things I'm looking for in my future partner.

Poor Kevin.

And one of them is 6 feet and he's 5'8". And he's like, you know, I'm not gonna get there. Right. And he's like, I was like, yeah, it's okay, I just want you to know.

And what did he say?

He was like, I don't meet half of these, but I'm happy to try.

Oh yeah, that's—

and I was like, yeah, it's okay if you don't meet him, I just want you to know.

What were—

what are some of the things on the list that are like personality-wise or things like that?

I think the, the personality traits one he already has, but I think there were things like, oh, I want him to know how to cook, or I want him to have have a very independent relationship with himself and not be a mama's boy. Like, I have a thing, I don't like mama's boys at all. And, um, I think having to speak Mandarin is really important to me. Like, it's not required, but you have to understand how much I love Taiwan.

And this is a tough list. Yeah.

And did he, did he rise to the occasion? Did he?

Yeah, yeah, yeah, yeah. Except for the 6 feet one. But, you know, we're still working.

He speaks Mandarin now?

Yeah. Oh no, no, he's always, he's always spoke, but he's like not very in tune. He's very like Asian American. And I'm, I'm very Taiwanese and like I love going back to Taiwan every year. So you have to know like that's part of my life.

Chloe, you would break my heart. I, I took, I took Chinese classes for like 4 years. I am way too dyslexic to be able to do that and cannot cook for my life. So I'm sorry, I hope your friendship list looks a little different. No, my favorite person is definitely romantic list because I am just hitting X's down this list.

We all have our strengths and weaknesses, don't worry. I can't cook for shit either.

Wait, what, what do you think people should take away from your experience with Kevin in terms of— for people who are looking for a partner right now, how do you think they should approach it?

I learned to not date the guy that looks good on paper and the guy that projects, like, you know, peacocking. Like, the people— oh God, the tech founder guys and the VC guys traumatized. Okay, but yeah, I think that people who look— who have too good of I'm gonna name drop, and I'm gonna— I, I— they're so stuck on their ways, and they have to look super successful, and they don't let their guard down. I think give me the biggest ick. And then people who like can have nothing and have a lot of fun and know how to just kind of talk to you as a person, um, I think they're my favorite people. And till this day, I still when I meet people, I see those in different people. And the projecting and then the peacocking comes from a place of insecurity. And I've dated the 6-foot, like, perfect on paper type of guys, and they're, they're working, they're working through stuff, and I don't want to work through it.

You ain't nobody's therapist.

I got enough work to do. I'm not trying to do that. Um, and then I think that because he's he's like so kind. He prioritizes me a lot. And I think a lot of the Type A, like a big business entrepreneur types, have to prioritize their work. And I don't want to be the second priority because life comes first. And you can have many jobs in your life, but you have one partner.

Yeah, that's really, really good advice. And it's— I kind of wanted to use that as an opportunity too to ask, like, what role do you think that a happy relationship plays in career? I keep seeing this discourse online that's like get your bag, focus on yourself, you don't need a man. So I'm curious what you think about that.

Get your bag. Yeah, let's go get it. But I— choosing your partner is the most important decision of your life. I think we all hear that. My take is he has redefined my bag, you know? Like, I used to be that annoying Silicon Valley, like, I want to be a CEO, tech startup founder, whatever. I want to be on Forbes. I want to be— and then, like, of course we all have those And then, um, I think that I came— I operated from a place of not like curiosity and passion, but more of that's what success looks like in the world and I want that and I want it so hard because I want to show people I'm better. And it wasn't like from a pure place and I felt like I was really negative towards myself. And I think he as my partner taught me that I, I'm always enough. Like, you already have enough. Your bag is enough. And it was enough yesterday. It's enough today and it'll be enough tomorrow. I think it's 'cause like he grew up in Michigan and his family, his dad was, worked at Ford all his life and worked on like a $90K salary and was a single like income for the whole family. And he's like, yo, and my life was great. Like worst case, we move back to Michigan. And, and I was like, I would hate that, but you're right. Like you did turn out better than I did.

So now no one's moving back to Michigan, but yeah.

Like as an LA girl, like it's kind of rough. But I think, I think that now I can be satisfied with my life and, and learn to be ambitious and dream hard in the ways that aren't from like a scarcity place. I think that's what he taught me. And I think that is what attributed that. That's what I attribute to my success. Yeah. You know, I think, you know, when you're going through the, going for the wrong goals, like you feel it deep in your heart and you burn out and then you like hate yourself and your, your discourse with your friends when you complain to your friends, You realize those patterns are because your intention was wrong in the first place. So he taught me how to find that core intention and, um, I'm really happy because of it. Yeah. And, and then he always goes, you know, when shit happens, you know what we gotta say? What do we say? We say, we say, you hate to see it. And then when things are great, you love to see it. And you know what? It's not that deep. Go next.

We're making a group chat with Kevin immediately after this episode. I'm sorry. Immediately. I need to see this guy's memes. I love this, this model of true partnership versus I think so much we get stuck on this idea of like the woman behind the man, the man successful and she supports him. Like the whole tradwife trend. It's exhausting to me. It's exhausting to me.

Yeah.

The idea that like, it's actually, it's really, it is rooted in a friendship.

That's such a beautiful lesson. And I'm really glad that we are, are ending on that. And you have such incredible worldly experiences. Thank you so much for coming on The Burnout today and sharing your story.

Thank you for having me.

Thank you so much, Chloe.