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Dating sucks in San Francisco

Good Work | July 10, 2026



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Ahhh San Francisco. The Golden City leads the world in many things: technology, bridges, and probably other stuff too. But it’s allegedly one of the worst places on Earth to date.

Dan Toomey takes the GW Investigative Plane to Hill City to see if it really deserves the name ā€œMan Franciscoā€ and if ā€œSFā€ is really short for ā€œSausage Festā€

Featuring interviews with

Kylie Robison, writer at host at Core Memory. Follow Kylie: https://x.com/kyliebytes

Celeste Amadon, founder of Known: https://known.com/

Lisa Catalano, creator of https://www.marrylisa.com/

Reagan Hsu, young man in SF. Follow Reagan or ask him out: https://www.youtube.com/@ReaganHsu123

Rachel Dec, writer in SF. Read Rachel’s stuff here: https://rachdele.substack.com/

Special thanks to Jack Raines. Check out his stuff and new book at https://www.youngmoney.co/

Thumbnail design: Seth Laupus
Audience development: Jen Walsh
Created by: Jack Stebbins, Henry Stockwell, and Dan Toomey

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FOLLOW DAN: https://www.instagram.com/dhtoomey/?h

Written by Good Work

Comments

This post currently has 38 comments.

  1. @snowshinobi

    July 10, 2026 at 6:53 pm

    That last line the video ends on, from Lisa, "I wasn't looking for a perfect man, I was looking for the perfect man for me" … That's wise.

    Dating apps can help ppl meet each other, as happened for Lisa and her beau, but they can also create doubt in people's minds. There's always someone better out there, just a swipe away.

    What are your hobbies? What are your life goals, your values? And sure, what's your career trajectory? You can use these touchstones to connect with like-minded people.

    I just think doing a social thing you wanted to do anyways — go to a poetry reading, ask someone to spot for you at the gym, etc — is a better way to potentially meet a life partner than rely on mixers and bars and other places where Dating itself is the purpose/theme.

    The point is not to get a relationship, any relationship will do. The point is to find a person you like who likes you too.

    Seeking connection in a broad, platonic sense can lead to mutual romantic curiosity. And if not, then you make a new friend.

  2. @ubechamporadoyum

    July 10, 2026 at 6:53 pm

    Not American but my American colleagues are so nice and some became my friends but my gosh, the dating horrors I heard are really one for the books. Btw, I'm married already for 8yrs. Hope to visit the US again soon.

  3. @zenlettering

    July 10, 2026 at 6:53 pm

    Dan! Please, and I'm dead serious now, please don't do the 'clickbait intro' with the 3 second cuts of 'this is what this episode is about!'. I really don't need a trailer for your video and I really don't want to watch some segments twice since you spoil them in the intro.

    like seriously guys, don't you have enough growth and viewers as is? Please don't be the basic clickbait btches

  4. @hardcorley

    July 10, 2026 at 6:53 pm

    A whole city of people firmly situated in their ego phase, fully aware that if they make it their entire life will be a fantasy. Sounds like the best place to discover a person willing to sacrifice for you, give you time and invest in a meaningful future.

  5. @Pascal112

    July 10, 2026 at 6:53 pm

    New pitch: we repackage DEI as "solving the gender ratio problem for dating in SF". We need tech companies to hire more women. Not because companies are more successful when there's a wide range of people with different perspectives and experiences in the room, but so you can date them.

  6. @Redmongoose-rdm

    July 10, 2026 at 6:53 pm

    Work for 5 years, stack your money, move, open a bakery and coffee shop and find love. Every time I think of this place, the first thing that comes to mind is that Steve McQueen movie, Bullitt.

  7. @Quicksymphony

    July 10, 2026 at 6:53 pm

    Not once did he mention the woman who was on the news and cat fished men to get rejected in person. Live. On mic and many of them were sent home.

    Natasha Aponte could be labeled a truth & major roadblock to the reality of dating.šŸ˜‚

  8. @da3dsoul

    July 10, 2026 at 6:53 pm

    I live in a college town as a 32 year old. I get it… The entire dating pool is 10 years younger than me and either "focusing on school" or spending 100k to party for 4 years and will regret it. The obvious answer is grad students, because they aren't 10 years younger or partying, and they might even have some free time to date, but…I have seen zombies more lively than grad students.

  9. @victoria-h4g2v

    July 10, 2026 at 6:53 pm

    Glory!!! šŸ™ŒšŸ¾ $85k biweekly, As single parent your videos really inspired me. Am 48, went from Grass to Grace. This video here reminds me of my transformation from a nobody to good home. To God be the glory.šŸ™ŒšŸ¾ā¤ļøā¤ļø

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