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Here is a summary of the transcript from YouTube, slightly edited with AI.
The Worst (and Best?) Cities in the World to Date
The Worst Cities for Dating, According to Time Out
Stephen, you had the data from Time Out on the worst cities in the world to date in. Take us through them.
They’re ranked in order of how bad they are—so number one is the worst. Let’s start from the bottom of the top 10.
#10 – Vienna
Vienna came in at number 10. None of us had strong opinions on dating in Vienna, and I can’t say I’ve ever dated there. If you’re listening from Vienna, let us know—are the rumors true?
#9 – Sydney
Sydney, Australia surprised us. It feels like such an outdoor, beachy culture. But then again, so is LA—and LA is notoriously tough for dating.
Maybe Sydney is easier in your 20s. Beach culture, social life, youth. Perhaps it gets trickier in your 30s, 40s, and beyond.
Joint #7 – London & Brisbane
London being on this list surprised me. I’ve always found London to be a great place to date—so many cultures, so much density, so much variety.
Maybe it’s the weather. Maybe it’s the cost of living. Big cities in general seem to rank low.
Joint #5 – Los Angeles & New York City
Los Angeles and New York were tied. LA being worse than London made sense. New York being tied with LA was more surprising.
New York feels easier logistically. You can be out already and meet someone across town in 15 minutes. In LA, that same invite is a 40-minute drive—and that’s if traffic’s good.
LA also has intense competition, especially around looks, status, and fame in certain circles. There’s hustle culture in both cities, but in different ways. In New York, people are relentlessly driven. In LA, there’s a currency around image and industry that can create pressure.
And in both cities, career ambition often competes with commitment.
#4 – Marseille
Marseille, France landed at number four. We don’t have strong insight into why. If you’re from Marseille, enlighten us.
#3 – Hong Kong
Hong Kong came in third worst. It may be the intense work culture or the transient expat lifestyle. When a city is highly career-focused and transient, dating can feel unstable.
#2 – Tokyo
Tokyo ranked second worst.
Culturally, Japan is often described as more reserved when it comes to approaching strangers. Social skills everywhere have shifted in recent years, and fewer people casually walk up and start conversations.
There are also traditional gender expectations that can create friction as women gain financial independence and redefine what they want in relationships.
Ironically, Tokyo might offer some of the most fun date ideas in the world. But fun activities don’t automatically equal easy connection.
#1 – Bilbao
The worst city to date in, according to this list, was Bilbao, Spain.
That surprised us. Bilbao has incredible food and culture. It’s not even a massive city. Which raises the question: if smaller cities struggle, shouldn’t many others be on the list too?
At a certain point, these rankings start to feel questionable.
What About the “Best” Cities?
Other lists ranked cities by percentage of single people, divorce rates, nightlife, and cost of living.
Some U.S. cities ranked highly for single availability and affordability:
- Salt Lake City, Utah
- Knoxville, Tennessee
- St. Louis, Missouri
Meanwhile, cities like San Jose, Fresno, and Bakersfield ranked low.
But here’s the problem: more single people doesn’t automatically mean better dating. A high divorce rate might mean availability—or it might mean instability.
The more you look at these lists, the clearer it becomes: there is no perfect city for dating.
Is It the City… or Is It Us?
In our 20s, we say dating in our 20s is the worst. In our 30s, we say everyone’s pairing off. In our 40s, we say everyone left is damaged or divorced.
We do the same with cities.
Yes, density helps. Being around more people statistically increases your chances. But no city on earth exists where no one wants a partner.
The idea that everyone in big cities is too busy chasing their career to want love simply isn’t true.
What is true is that in big cities, competition is higher—and you have to stand out.
But standing out doesn’t mean being extraordinary. It means being proactive.
The Power of Micro-Interactions
Most people obsess over the “big move”—walking across the room to talk to someone.
But what about the 100 tiny moves before that?
- Making eye contact
- Positioning yourself in an open way
- Commenting on someone’s drink
- Saying “cheers” at the bar
- Giving a genuine compliment
These micro-interactions signal warmth and approachability.
If you walk into a room and talk to everyone—not just the person you’re attracted to—you warm yourself up. Then, when someone catches your eye, it’s no longer a massive leap. It’s just an extension of how you’re already behaving.
Tourists do this naturally. They talk to everyone because they’re only in town for three days. They engineer adventure.
Back home, we freeze. We protect our pride. We don’t want to embarrass ourselves in “our” coffee shop.
Your pride can become your enemy.
Big City vs. Small City Advice
If You Live in a Big City:
Don’t hide behind the idea that everyone is too busy or unavailable. Engineer connection. Be brave. Create community.
If You Live in a Small City:
Acknowledge you’ll have fewer options—but that means you must be more proactive.
- Join groups intentionally.
- Build community consciously.
- Widen your dating app radius.
- Be willing to drive for a date.
You may have to sacrifice convenience for options.
Money, Values, and Partnership
We also received thoughtful emails about money in relationships.
One listener pointed out that many financially independent women aren’t looking for men who earn more—they’re looking for equals with similar values.
Another highlighted that even couples with similar incomes can struggle if their financial priorities differ—saving versus spending, relocating versus staying, investing versus indulging.
The real issue isn’t income. It’s alignment of values.
How we spend money reveals what we prioritize. Lifestyle expectations, generosity, risk tolerance, long-term goals—these matter far more than raw earnings.
Dating at 53: Is a Huge Age Gap a Red Flag?
We also heard from Janelle, who asked about dating at 53 and whether it’s a red flag when men her age have dated women in their 20s.
It’s understandable to find that off-putting.
The key question isn’t whether it happened once—it’s whether it’s a pattern.
If someone consistently dates 20 or 30 years younger, that may reveal something about their values or maturity preferences.
But one relationship doesn’t define someone’s entire character.
What matters more is how they talk about it:
- Did they learn something?
- Did it shift their values?
- Do they now want deeper compatibility?
Patterns matter more than isolated experiences.
Final Thought: There Is No Perfect Place
No perfect city.
No perfect age.
No perfect dating pool.
There are only environments where we either hide… or show up.
Your city doesn’t determine your love life nearly as much as your courage does.
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This post was previously published on YouTube.
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