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Tony Hawk as Larry David is still the best Halloween costume

I went to Manila, Philippines to visit my virtual assistants last week We have worked together closely for over 1 year now I could not run my life without their help! They picked me up at the airport in a new car that one bought thanks to her job with me Then I took them out for lots of meals, like the Chinese hot pot buffet in this photo They taught me some words in Tagalog One day we had a big work meeting We talked about all the things I do, future plans, etc They asked me a lot of questions and it was helpful for all We talked about my book “The 2-Hour Cocktail Party” and all the things we have planned next They support my readers for party coaching and helping me give out advice on how to make friends and help people grow their networks It was pretty great! I’m so glad that I went to visit them But I realized that calling them “virtual assistants” isn’t a fair term It feels outdated, like calling someone Oriental These are real team members — not a SaaS or a line item expense So I think I’ll stop using the term VA or Virtual Assistant soon I’m thankful for their help and plan to hire another person soon to continue to grow my team

I would like to introduce you now to my Tokyo Blind Date She works as a mechanical engineer in the medical device industry I am not going to give her name for her privacy but maybe she will post here on my account soon She saw my post for the trip and sent me an email Her

telling all my Bumble matches I’m a single issue voter and that issue is the Jones Act, a 100 year-old law that restricts shipping between United States ports to American-owned ships and costs us billions of dollars each year

I’m at a capybara cafe in Tokyo now These things are huge! You can get a coffee and hang out with them for $7 Very friendly and chill

Almost every single unmarried 40-year-old man that I know wants to marry a woman aged 28 - 32

The sun rises early here in Japan We were supposed to leave last night To fly home and end this crazy Tokyo Blind Date Originally I thought that three days was the absolute maximum amount of time you would want to spend with a stranger in a foreign land But things change // When you first fly in, you can see that Tokyo is big There are more people in the Tokyo sprawl than all of Canada Human life is so densely packed here. It is the most populated metropolitan area in the world Each major neighborhood could be its own little city I still want to show her around the fancy streets of Ginza, walk through the American areas of Roppongi, and taste what’s left of the old fish market I think we need more time. I’m nervous to ask but I want to stay longer “I have a crazy idea,” I say. “Do you want to stay to Tuesday? Stay and give us another day or two to explore?” I imagine all the possible answers and of course I focus on the worst thing she might answer- that she wants to stick to the plan and not extend the trip Then I will believe it is my fault. That I’m not fun enough, or not a good tour guide, or that my jokes are wearing thin or my muscles are not so big and that her laughs are not as deep And then in that moment I will know that the date will be over The date will be over not at the airport saying goodbye, not when the plane takes off, but at the exact moment that she tells me right now that she does not want to stay She looks up. “Another day or two?” I nod and shrug my shoulders, prepared for my defeat but proud that I tried “Yeah! Let’s do it.” I exhale. And smile. And then I book the flights // Maybe three days is the most amount of time you would want to spend with a stranger in a foreign land But maybe she’s not a stranger to me now So we will spend two more days to make it a total of five We fly out on Tuesday night And we get two more sunrises in Tokyo to explore

This is a message for single men that are tired of online dating I made a post 6 months ago about what I should text a woman that I was going on a date with The date was great. In fact we have spent almost every day since then together Now she’s my girlfriend Guys if you’re frustrated with online dating I have some advice Delete your dating apps and start going out every single day You need to the gym, go to the grocery store, go work from cafes You need to try a new group fitness class every other day, go to yoga and pilates, and join meetups for things you’re interested in Be someone who is out and about Talk to strangers, make friendly conversation, add value, and don’t be sketchy Find fun things happening in town that you can invite people to I guess that’s pretty complicated so try this for now: Start saying yes to every single invitation that you get What you want as a single guy- and this is key- is IRL surface area You want to get out of your home and off your phone so that you improve your odds to meet someone special in real life That’s what I am calling your IRL surface area I knew I needed this IRL surface area because I do bad on dating apps See I’m not 6-feet tall and I don’t have a chiseled jaw But I do feel comfortable talking to strangers I met my girlfriend at the pool on a hot summer Tuesday evening My friend Katelyn invited me to come hang out with her and her friends I was busy with work and I didn’t want to go but thank God I did I went to the pool that day because I wanted to say Yes to everything that would help me find a girlfriend Sitting at home doing work = No Going to Barton Springs Pool = Yes She was sitting up on the hill reading a book. I mustered up the courage to go chat but that’s another story For now just go out. Every day. Make it a challenge if you want: Go out every day for 10 days straight starting tomorrow Try new restaurants, coffee shops, all the things I said above Just start talking to people and doing the things that the person you want to date might do too You can find a girlfriend if you get more IRL surface area Here’s a photo of us on the beach yesterday Good women are out there. You just have to put in the work

Life pro tip: you don’t have to check out of hotels. You can just leave. It is awesome

I have a first date on Sunday night I am taking her out for sushi I will use the most popular reply to this post as my text message to remind her about our date tomorrow

It is late - I’m always late We are running through side streets of Tokyo’s most elegant neighborhood to make our dinner reservation She's wearing eyeliner and I have on my least-wrinkled shirt It will be our last big meal together and I want to make it special In two hours

Please remember the Native Americans this Thanksgiving

We're up early for one last sushi breakfast. Maybe a walk I have a headache. It's probably the melatonin I took last night to help me sleep. But I’m determined to make the morning right We arrive at the best spot in the old fish market. Hours went into finding this place but she doesn’t need to know that Over a piece of tuna I ask: Do you even like me? She smiles. "I'm still here, aren't I?" // We walk in shops I otherwise would not We stay out longer than I usually would We sit to watch the city on a bench meant for two We talk about the trip, what's back home, our past relationships We search for ice cream and fake-fight about who should get the last bite This is traveling together // The train ride to Narita Airport seems shorter this time She's at the window staring out. I am beside, typing these notes and thinking about how this whole thing got started Posting my Tokyo Blind Date seemed like a fun excuse for me to go back to Japan Maybe when you first heard about it you thought it was a gimmick or ridiculous And I fully acknowledge that I am ridiculous But I also got a look at something very real here. And stories that start ridiculous can end up very real and very deep // There is no grand plan for an airport goodbye We hug one last time as they call my flight for boarding It is a good hug, a full body embrace that holds and lingers, and I know I will see her again // Perhaps my story resonated with so many because we want the Internet to be a good place and we want people to find love I mean, you don’t read my posts and say, “Yes I remember the time that I, too, solicited strangers on the Internet to go to Tokyo.” Now I know a lot of people are hoping that this story ends with a proposal Or that we both declare our love and I’m typing this in bed beside her right now But I understand enough about relationships to know that a long weekend together is not enough for a lifelong commitment And what this represents is a beginning I first said that I just wanted to travel to Japan with someone cute But I think I could not fully admit that I wanted to find a girlfriend I could not admit that even to myself I realize now that it is four years since my last serious relationship ended I am getting older and wiser and yet I guess I have been alone for a very long time This trip made me realize what I’ve been missing Maybe I’m finally ready to share my life with someone again // A beginning is a beautiful, wonderful thing Whether that leads to Happily Ever After or it ends in an amazing blind date that I’ll remember for the rest of my life... I’ve at least learned that I’m ready to find that right person If there is anything to take away from this experience it's this: Please live a good story Do it for the plot. I’m telling you it is worth it And find someone to do it with you, because it is way more fun when you’re not alone If you’re a person who is alone or afraid to step out into the world to find your person, know that for the last four years, that has been me On this trip I’ve learned how foolish I was to wait for so long So take my advice and learn from my example. Don’t think that you can’t seek someone special in the world and maybe find your person There are people out there who are waiting for their beginnings with you, too Seeking a beautiful beginning is what we should all be looking for Because eventually beginnings lead to Happily Ever Afters

I got engaged this past weekend. We're going to get married and then hopefully start a family. That might be enough of a post for most people But since I've been public with my dating life, I want to reflect on this for a moment A year ago, the thought of getting married wasn't even on my radar. And yet now I'm in love. So I'll tell you what I did. And I'll tell you how I changed my mental models on dating, why I love this woman, and what comes next. First, my life was pretty good Or at least it felt incredibly full. I built businesses and made some good investments. I lived in NYC, moved to Austin, and just generally loved the thrill of dating and hosting events. My freedom is what I valued the most. I could fly anywhere in the world on a whim I could pack a bag and go to Japan just for fun, and then leave the moment I got bored. Being single felt like absolute freedom. I loved it. But about a year ago, something changed. I did the Tokyo blind date thing. Then my sister had a baby. And all my best friends started having kids. I looked around at my life and things just felt a bit more flat. The dating experiences that used to thrill me were starting to feel empty. I was getting older, too, and I started to feel like my time was running out. I realized that I wanted more. I wanted to share my life with someone, and I wanted to start a family. So I got strategic about it. Which I know is super nerdy and doesn't feel romantic, but I had to change something major with my lens on dating I read books on relationships, I interviewed friends in happy marriages, and I thought a lot about what my non-negotiables were. I created a framework: big stuff versus small stuff. Small stuff was what I'd always focused on. Looks, style, wit. These are the things for me that create instant attraction. Big stuff was the foundation. Values, wanting kids, where they want to live, how they treat people, and what a successful partnership means to them. For too long, I'd screened for the small stuff first. Attractive? Check Fun? Check. Good enough! But finding a life partner meant flipping the order. I thought I knew what I wanted, but my intuition about what would lead to long-term happiness was often dead wrong. I had to look at the big stuff first and be willing to walk away if it didn't align, no matter how gorgeous or charming they were. So I started being direct on dates and telling people that I was interested in a serious relationship. Then came the hard part: showing up. One Tuesday evening, dead tired from work, my friend Katelyn invited me to Barton Springs Pool. Every bone in my body wanted to stay home and keep working. But I went anyway. Lauren was up on the hill reading a book. She looked supermodel beautiful and was exactly my type. The book caught my attention. She was reading Being Mortal by Atul Gawande, which is not exactly a fun poolside read. I walked over to chat her up. Small stuff got me there, but the big stuff kept me talking. She had a rare confidence and a quick wit. When she talked about her family, there was a warmth I didn't know I'd been looking for. Three hours into our first date, I asked her if we should get married. But that was too bold. She laughed it off and said she'd think about it. That was ten months ago. We've spent nearly every day together since and moved in together earlier this year. Now she's become my best friend. When I get too intense, she grounds me. When I miss details, she catches them all. She pushes me to grow in ways I'd never push myself. Lauren has a rare gift of social grace. She can talk to anyone about anything. Venture capital one minute and cowboy boots the next. The first time I joined her family for Rosh Hashanah they welcomed me with open arms. They roasted me, teased me about my affinity for name tags, and brought me into their world. Seeing how close they all are - how Lauren talks to them daily, how proud she is of her brothers and cousins and dad - I thought, "I want this. I like this." Last weekend was her birthday. We went out to California to talk about our future. About kids and about what building a life together really means. I asked her again if she'd marry me, and this time she said yes. It feels big. It feels right. And I'm super happy for what comes next.

This is Robert. He started a business in NYC with zero money. 10 years ago he began waiting in long lines for rich people. But then Robert did something very special...

I am hosting a Tokyo meetup now 👋 These people saw my Tokyo Blind Date posts and we are all hanging out in the park today I brought name tags for everyone and have been leading rounds of intros to help everyone make new friends The weather is so nice today!

Almost every single unmarried 40-year-old man that I know wants to marry a woman aged 28 - 32

Today I walked out of a doctors office after they were 30 minutes late to see me “Can I just do this later? I’ve been waiting for 30 minutes and I have a meeting— I’ll call to reschedule” The front desk seemed shocked but I wasn’t trying to make a big deal out of it No lesson

I got engaged this past weekend. We're going to get married and then hopefully start a family. That might be enough of a post for most people But since I've been public with my dating life, I want to reflect on this for a moment A year ago, the thought of getting married wasn't even on my radar. And yet now I'm in love. So I'll tell you what I did. And I'll tell you how I changed my mental models on dating, why I love this woman, and what comes next. First, my life was pretty good Or at least it felt incredibly full. I built businesses and made some good investments. I lived in NYC, moved to Austin, and just generally loved the thrill of dating and hosting events. My freedom is what I valued the most. I could fly anywhere in the world on a whim I could pack a bag and go to Japan just for fun, and then leave the moment I got bored. Being single felt like absolute freedom. I loved it. But about a year ago, something changed. I did the Tokyo blind date thing. Then my sister had a baby. And all my best friends started having kids. I looked around at my life and things just felt a bit more flat. The dating experiences that used to thrill me were starting to feel empty. I was getting older, too, and I started to feel like my time was running out. I realized that I wanted more. I wanted to share my life with someone, and I wanted to start a family. So I got strategic about it. Which I know is super nerdy and doesn't feel romantic, but I had to change something major with my lens on dating I read books on relationships, I interviewed friends in happy marriages, and I thought a lot about what my non-negotiables were. I created a framework: big stuff versus small stuff. Small stuff was what I'd always focused on. Looks, style, wit. These are the things for me that create instant attraction. Big stuff was the foundation. Values, wanting kids, where they want to live, how they treat people, and what a successful partnership means to them. For too long, I'd screened for the small stuff first. Attractive? Check Fun? Check. Good enough! But finding a life partner meant flipping the order. I thought I knew what I wanted, but my intuition about what would lead to long-term happiness was often dead wrong. I had to look at the big stuff first and be willing to walk away if it didn't align, no matter how gorgeous or charming they were. So I started being direct on dates and telling people that I was interested in a serious relationship. Then came the hard part: showing up. One Tuesday evening, dead tired from work, my friend Katelyn invited me to Barton Springs Pool. Every bone in my body wanted to stay home and keep working. But I went anyway. Lauren was up on the hill reading a book. She looked supermodel beautiful and was exactly my type. The book caught my attention. She was reading Being Mortal by Atul Gawande, which is not exactly a fun poolside read. I walked over to chat her up. Small stuff got me there, but the big stuff kept me talking. She had a rare confidence and a quick wit. When she talked about her family, there was a warmth I didn't know I'd been looking for. Three hours into our first date, I asked her if we should get married. But that was too bold. She laughed it off and said she'd think about it. That was ten months ago. We've spent nearly every day together since and moved in together earlier this year. Now she's become my best friend. When I get too intense, she grounds me. When I miss details, she catches them all. She pushes me to grow in ways I'd never push myself. Lauren has a rare gift of social grace. She can talk to anyone about anything. Venture capital one minute and cowboy boots the next. The first time I joined her family for Rosh Hashanah they welcomed me with open arms. They roasted me, teased me about my affinity for name tags, and brought me into their world. Seeing how close they all are - how Lauren talks to them daily, how proud she is of her brothers and cousins and dad - I thought, "I want this. I like this." Last weekend was her birthday. We went out to California to talk about our future. About kids and about what building a life together really means. I asked her again if she'd marry me, and this time she said yes. It feels big. It feels right. And I'm super happy for what comes next.

I would like to introduce you now to my Tokyo Blind Date She works as a mechanical engineer in the medical device industry I am not going to give her name for her privacy but maybe she will post here on my account soon She saw my post for the trip and sent me an email Her

I'm giving away $43,000 today to a bunch of charitable organizations Tell me which org you like best and maybe I will send them $1k each and $5k to my favorites It is my 43rd birthday today so I want to give away $43k because it seems fun Things I am interested in funding: - entrepreneurship and tech - animal stuff like shelters - Texas things supporting local - pro-America and Veterans help Disclaimer: must be a USA-based 501(c)3 org because of taxes I am open to other ideas and I love small scrappy orgs Please reply here with your suggestions I will link a page below of each place that I donate to and you can see my past charitable giving there too

press and PR question-- I have received inquiries from the BBC, Washington Post, PEOPLE magazine, and my favorite podcast (My First Million) to talk about my Tokyo Blind Date story but I sort of don't want to do any of them Is that crazy? I feel like talking about this in an

We're up early for one last sushi breakfast. Maybe a walk I have a headache. It's probably the melatonin I took last night to help me sleep. But I’m determined to make the morning right We arrive at the best spot in the old fish market. Hours went into finding this place but she doesn’t need to know that Over a piece of tuna I ask: Do you even like me? She smiles. "I'm still here, aren't I?" // We walk in shops I otherwise would not We stay out longer than I usually would We sit to watch the city on a bench meant for two We talk about the trip, what's back home, our past relationships We search for ice cream and fake-fight about who should get the last bite This is traveling together // The train ride to Narita Airport seems shorter this time She's at the window staring out. I am beside, typing these notes and thinking about how this whole thing got started Posting my Tokyo Blind Date seemed like a fun excuse for me to go back to Japan Maybe when you first heard about it you thought it was a gimmick or ridiculous And I fully acknowledge that I am ridiculous But I also got a look at something very real here. And stories that start ridiculous can end up very real and very deep // There is no grand plan for an airport goodbye We hug one last time as they call my flight for boarding It is a good hug, a full body embrace that holds and lingers, and I know I will see her again // Perhaps my story resonated with so many because we want the Internet to be a good place and we want people to find love I mean, you don’t read my posts and say, “Yes I remember the time that I, too, solicited strangers on the Internet to go to Tokyo.” Now I know a lot of people are hoping that this story ends with a proposal Or that we both declare our love and I’m typing this in bed beside her right now But I understand enough about relationships to know that a long weekend together is not enough for a lifelong commitment And what this represents is a beginning I first said that I just wanted to travel to Japan with someone cute But I think I could not fully admit that I wanted to find a girlfriend I could not admit that even to myself I realize now that it is four years since my last serious relationship ended I am getting older and wiser and yet I guess I have been alone for a very long time This trip made me realize what I’ve been missing Maybe I’m finally ready to share my life with someone again // A beginning is a beautiful, wonderful thing Whether that leads to Happily Ever After or it ends in an amazing blind date that I’ll remember for the rest of my life... I’ve at least learned that I’m ready to find that right person If there is anything to take away from this experience it's this: Please live a good story Do it for the plot. I’m telling you it is worth it And find someone to do it with you, because it is way more fun when you’re not alone If you’re a person who is alone or afraid to step out into the world to find your person, know that for the last four years, that has been me On this trip I’ve learned how foolish I was to wait for so long So take my advice and learn from my example. Don’t think that you can’t seek someone special in the world and maybe find your person There are people out there who are waiting for their beginnings with you, too Seeking a beautiful beginning is what we should all be looking for Because eventually beginnings lead to Happily Ever Afters

I have a first date on Sunday night I am taking her out for sushi I will use the most popular reply to this post as my text message to remind her about our date tomorrow

I went to Manila, Philippines to visit my virtual assistants last week We have worked together closely for over 1 year now I could not run my life without their help! They picked me up at the airport in a new car that one bought thanks to her job with me Then I took them out for lots of meals, like the Chinese hot pot buffet in this photo They taught me some words in Tagalog One day we had a big work meeting We talked about all the things I do, future plans, etc They asked me a lot of questions and it was helpful for all We talked about my book “The 2-Hour Cocktail Party” and all the things we have planned next They support my readers for party coaching and helping me give out advice on how to make friends and help people grow their networks It was pretty great! I’m so glad that I went to visit them But I realized that calling them “virtual assistants” isn’t a fair term It feels outdated, like calling someone Oriental These are real team members — not a SaaS or a line item expense So I think I’ll stop using the term VA or Virtual Assistant soon I’m thankful for their help and plan to hire another person soon to continue to grow my team

The sun rises early here in Japan We were supposed to leave last night To fly home and end this crazy Tokyo Blind Date Originally I thought that three days was the absolute maximum amount of time you would want to spend with a stranger in a foreign land But things change // When you first fly in, you can see that Tokyo is big There are more people in the Tokyo sprawl than all of Canada Human life is so densely packed here. It is the most populated metropolitan area in the world Each major neighborhood could be its own little city I still want to show her around the fancy streets of Ginza, walk through the American areas of Roppongi, and taste what’s left of the old fish market I think we need more time. I’m nervous to ask but I want to stay longer “I have a crazy idea,” I say. “Do you want to stay to Tuesday? Stay and give us another day or two to explore?” I imagine all the possible answers and of course I focus on the worst thing she might answer- that she wants to stick to the plan and not extend the trip Then I will believe it is my fault. That I’m not fun enough, or not a good tour guide, or that my jokes are wearing thin or my muscles are not so big and that her laughs are not as deep And then in that moment I will know that the date will be over The date will be over not at the airport saying goodbye, not when the plane takes off, but at the exact moment that she tells me right now that she does not want to stay She looks up. “Another day or two?” I nod and shrug my shoulders, prepared for my defeat but proud that I tried “Yeah! Let’s do it.” I exhale. And smile. And then I book the flights // Maybe three days is the most amount of time you would want to spend with a stranger in a foreign land But maybe she’s not a stranger to me now So we will spend two more days to make it a total of five We fly out on Tuesday night And we get two more sunrises in Tokyo to explore

It is late - I’m always late We are running through side streets of Tokyo’s most elegant neighborhood to make our dinner reservation She's wearing eyeliner and I have on my least-wrinkled shirt It will be our last big meal together and I want to make it special In two hours

This is a message for single men that are tired of online dating I made a post 6 months ago about what I should text a woman that I was going on a date with The date was great. In fact we have spent almost every day since then together Now she’s my girlfriend Guys if you’re frustrated with online dating I have some advice Delete your dating apps and start going out every single day You need to the gym, go to the grocery store, go work from cafes You need to try a new group fitness class every other day, go to yoga and pilates, and join meetups for things you’re interested in Be someone who is out and about Talk to strangers, make friendly conversation, add value, and don’t be sketchy Find fun things happening in town that you can invite people to I guess that’s pretty complicated so try this for now: Start saying yes to every single invitation that you get What you want as a single guy- and this is key- is IRL surface area You want to get out of your home and off your phone so that you improve your odds to meet someone special in real life That’s what I am calling your IRL surface area I knew I needed this IRL surface area because I do bad on dating apps See I’m not 6-feet tall and I don’t have a chiseled jaw But I do feel comfortable talking to strangers I met my girlfriend at the pool on a hot summer Tuesday evening My friend Katelyn invited me to come hang out with her and her friends I was busy with work and I didn’t want to go but thank God I did I went to the pool that day because I wanted to say Yes to everything that would help me find a girlfriend Sitting at home doing work = No Going to Barton Springs Pool = Yes She was sitting up on the hill reading a book. I mustered up the courage to go chat but that’s another story For now just go out. Every day. Make it a challenge if you want: Go out every day for 10 days straight starting tomorrow Try new restaurants, coffee shops, all the things I said above Just start talking to people and doing the things that the person you want to date might do too You can find a girlfriend if you get more IRL surface area Here’s a photo of us on the beach yesterday Good women are out there. You just have to put in the work

Bangalore has the BEST weather and nobody is talking about it

Self care ideas for men: - Getting a car wash - Going to Costco - Buying domain names - Sending memes to group text What else?

If you work in technology and drive anything besides a Tesla, I can’t take you seriously

Unpopular opinion: In-N-Out Burger is trash