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

0:00You telling me this is your first time going on a date with a woman. Chloe Shih 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 four things that have a 90 % of predictability of whether your marriage is going to fail. And number one is I'm Chloe Shih and this is The Burnouts.

0:30Sophia: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 we went to do, we started couples therapy probably like nine 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 started couples therapy and we still do it today.

1:02And 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 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 coaches for personal training. But we don't have someone to help with our biggest decision in life. and also people who seek couples therapy there I think that I think like either 60 % or 90 % of couples their communication improves their children are less traumatized or more emotionally stable and 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 spend about like six years before they seek couples therapy and imagine all the resentment that builds across six 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 a problem.

2:17We learn how to talk when things are vague and share hard conversations because never a good time to talk about hard conversations. It never is. Yeah.

2:27Sophia: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 was not as in touch with his emotions as the women are. And I was like already going through my own personal therapies 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.

3:14So 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. You have enough.

3:33Sophia: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 I read that there is a concept called the four horsemen of the marriage apocalypse by Dr. John Gottman. 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 like 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 uh 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 you sometimes you run away Sometimes you just say nothing and that's not coming in.

5:07So I think learning about, oh, if we can solve and learn our muscles around these four problems, then I think we can solve a lot of issues. 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 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 they're 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

5:50Sophia: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 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?

6:22Sophia: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 sign you up i didn't sign you up oh my god 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.

6:56I 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, in your 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 not 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.

7:29Be like, hey, you want to come to my thing? My coworkers are there. And then I met him there and he wanted to say what's up. And I was like, oh, 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. 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 you around and obviously he's like not doing anything because he's an engineer and he's like yeah of course and he comes down to the game room and he brings a group of boys and they're like playing smash melee in the game room at twitch and I'm like it's 11 a.m 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 that why was it horrible um because because it was his first time he was his first is 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 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've 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

9:43Sophia:like a lot of people don't want to date a guy who's like oh it's your first girlfriend oh i'm gonna have to teach him everything but then other people yeah love it for sure i felt that i felt that i was like i'm gonna be a mother i'll be a mother again a mother of a child um no one likes being a mother i don't 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 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 yeah yeah the football what is that no what i don't know um in the bay area uh girls are called 49ers fours who think they're nines 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 incelty type 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 Peak 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's 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 yeah 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.

11:52He 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 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 he's really smart. He went to UMich. He's like a very smart cookie and we love UMich. Yeah it's

12:20Sophia:it's great if you go to umish 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 okay okay but what did he say about what if he wanted 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 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 six 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 sequel because i was like trying to build dashboards oh god not sequel give me bring up my pdlc i hate 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 a holiday company holiday party at facebook 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 i know yeah did you tell me in jail put me in jail no no i am all for Kevin.

14:37Yeah, you were so patient with Kevin. This is a beautiful story. So you invited Kevin as your friend. Yeah, as my friend.

14:45Sophia:No, I think that the story here is that Kevin is the the like the rebound king. What is it called when you come back from nothing? 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 girlfriend 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 be like what do you think of this and kevin's like well here's my take but also know that i I don't have any experience.

15:33Wow. And so tell us. So you guys go to this Facebook prom together. Yes, we go to Facebook prom together. And then we're like going on the dance floor. And the man starts busting out and like just break dancing. And I'm like, huh? Who is this software engineer, dual monitor, mechanical keyboard, RGB loving, melee playing guy? And were you like, whoo? Yeah. And he's break dancing? Yeah, man is break dancing 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 I have a friend who's going to stay at my place. A lot of people in South Bay, you know, they'll crash in San Francisco, live in San Francisco.

16:13So I'm supposed to take him to my place. And so Kevin afterwards, putting Kevin on blast, Kevin was like, all right, you better listen up because I'm only going to 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 had 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 and one of them is six feet and he's five eight and he's like you know i'm not gonna get there right he's like i was like yeah but it's okay i just want you to know what what did he say he was like i don't meet half of these but i'm happy to try yeah that's and i was like yeah it's okay if you don't meet him i just want you to know

17:18Sophia:what were what are some of the things on the list that are like personality wise or things like that I think 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 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 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. This is a tough list. Yeah. And did he rise to the occasion? Yeah, yeah, yeah. Except for the six feet one.

17:55But, you know, we're still working on it. He speaks Mandarin now? Yeah. Oh, no, no. He's always spoke. But he's, like, not very in tune. He's very, like, Asian American. And 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.

18:08Sophia:Chloe, you would break my heart. I took Chinese classes for, like, four 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 friendship list is definitely different. Then you're a 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. 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?

18:36I learned to not date the guy that looks good on paper and the guy that projects, like, you know, peacocking. Yeah. The tech founder guys. And the VC guys. I'm traumatized. Okay. But yeah, I think that people who look, who have too good of, I'm going to name drop and I'm going to, 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. I think they're, they're my favorite people. And till this day, I still, when I meet people, I see those in different people.

19:24And the projecting and then the peacocking comes from a place of insecurity. And I've dated the six foot, like, perfect on paper type of guys. And they're working through stuff. And I don't want to work through it.

19:39Sophia:You ain't nobody's therapist. I got enough work to do. I got enough work to do. I'm not trying to do that. um and then I think that because 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 to to ask like what role do you think that a happy relationship plays in career I I keep seeing this discourse online that's like, get your bag, focus on yourself.

20:17You don't need a man. So I'm curious what you think about that. Get your bag. Yeah, let's go get it. But 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 dreams 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 um i i'm always enough like you already have enough your bag is enough and it was enough yesterday it's enough today and i'll be enough tomorrow i think it's because 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 moved back to michigan and i was like i would hate that but But you're right.

21:36Like you did turn out better than I did.

21:37Sophia:So now no one's moving back to Michigan. But yeah, like as an L.A. girl, like it's kind of rough. But I think I think that now I can be satisfied with my life 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, 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 got to 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?

22:32It's not that deep. Go next.

22:35Sophia: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 model of true partnership versus I think so much we get stuck on this idea of like the woman behind the man. The man's successful and she supports him. Like the whole trad wife trend. It's exhausting to me. It's exhausting to me. 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 burnouts today and sharing your story thank you for having me thank you so much