Is There a "Best" City to Date In? The Love Life Podcast Ranks the Rankings

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Overview

On this episode of the Love Life podcast, Matthew Hussey, Audrey, Stephen and producer David go through published rankings of the best and worst cities in the world for dating. They treat the lists with open skepticism, and several times admit they know little about the places being ranked. The conversation soon moves to a bigger question: how much does your city actually determine your dating life, and how much is it something people blame when they're frustrated? Matthew's position, which he develops at length, is that density and circumstances matter, but that people in big cities and small towns alike tend to underuse the opportunities they already have. The episode also covers two listener emails about money and relationships, a voice-note question about age gaps, and a closing game matching cities to romantic scenarios.

25 min read
0:16

The Time Out List of the Worst Cities to Date In

Stephen had a list from Time Out of the worst cities in the world for dating. He later said the metric was love-life satisfaction reported by locals. He read it from tenth-worst to worst.

Vienna came tenth. No one on the panel had dated there, and Matthew asked listeners in Vienna to write in and say whether it deserved the spot. Sydney was ninth, which surprised the group because of its outdoor culture. Someone replied that Los Angeles also has an outdoor culture and is considered hard to date in. Matthew guessed Sydney might be a good place to date if you're in your twenties and at the beach, and harder in your thirties, forties or fifties.

London and Brisbane tied for seventh. Stephen was surprised by London. He had always called it a great dating city because it's dense and draws people from all over the world, so "you can get any kind of person." The others guessed at rain, bad weather and cost as explanations. Asked about her time living in London, Audrey said she also enjoyed dating there, which prompted some teasing from Matthew.

2:33

Los Angeles vs. New York

Los Angeles and New York tied for fifth. Most of the panel thought New York was the better of the two. One host said you could have "three dates in one night in New York," and someone else answered that this might be exactly the problem. They agreed the two cities are hard for different reasons.

The case against LA was high competition, especially on looks, many famous people, a spread-out geography, and a lot of people working in the same industry. Matthew objected that people forget how big LA is: it isn't only the entertainment world, and plenty of people there do many different kinds of jobs. He still agreed that people in LA stay indoors a lot and that it's hard to get anyone to do anything.

Audrey framed it around each city's values. She called New York a "hustler city" where people have to sink or swim, and where finding love and settling down may not be most people's priority, so dating can feel casual and transient. In LA she saw "a currency around fame and status" in some pockets of the city. Going on a date with someone who holds those values could leave you feeling inadequate. She added that she had never dated in LA herself.

Matthew said LA has its own hustle culture, because many people gave up a lot to move there for a dream, and that can make nothing else feel allowed to get in the way. For him the bigger factor is sprawl. He said it raises the "activation energy" for doing anything. In New York, if you're already out and friends text you to join them at another bar, it's a quick cab ride. In LA the same invitation means a 40-minute drive, and once you've committed to one place you tend to stay there. One of the hosts also said they believed New York skews female in its numbers, which is a reason some women there complain.

5:53

Marseille, Hong Kong, Tokyo and Bilbao

Marseille came fourth. No one could explain it. The others joked that Audrey, as the closest thing they had to a French correspondent, should answer for it. Hong Kong was third. The guesses were a large expat population, an intense work culture, and a dating scene that is active but transient.

Tokyo came second, and this got a longer discussion. Matthew said it's increasingly uncommon everywhere for people to walk over and talk to a stranger. In his view, men in recent years have become more worried about looking creepy, and people's social skills in general have eroded. As he understands it, Japan has been "leading the pack" on this for a long time.

Audrey added another factor, which she said is based on anecdotes from people she has spoken to. In a fairly traditional country with traditional gender-role expectations, women who move up in their careers and gain independence may see a relationship as coming with the expectation that they become something like a housewife. Many don't want that. She said this creates friction between the genders and is also hard on men, who may want something women don't feel able to offer right now. Someone noted the irony that Tokyo may offer the most fun dates anywhere because there's so much to do besides drinking. The others joked about three dinners, then McDonald's, then karaoke.

The worst city on the list was Bilbao, Spain. No one had been there. Someone asked whether it's known for excellent restaurants. Another host said that if a city of Bilbao's size is on the list, plenty of other small cities should be too. Matthew then said the panel wasn't qualified to judge most of these cities, including the ones they had opinions on. He called Time Out's list "questionable" and asked listeners from those places to write in.

10:14

The "Best Cities" Lists and Their Contradictions

David brought two lists of the best cities. Before he started, he said he was surprised San Francisco wasn't on the worst list, because he often hears women say it's hard to date there.

The first list ranked cities by the percentage of single people, and it listed the percentage of divorced people separately. The panel was confused by that. They wondered whether a lot of divorce was meant to count as a good sign because it means more available people, and why that wasn't already covered by the single figure. Someone called it a "poisoned chalice": lots of available people, but also more divorce. Another joked that you'll find love and then lose it. Going up from the bottom of the top ten, David read Berlin, San Francisco, Chicago, Barcelona and Stockholm.

Chicago made sense to some of the panel, who described it as a less intense New York with more Midwestern vibes and people more willing to commit. They mentioned a couple from Chicago they met on holiday who had married at about 26. A figure of 62% single was also mentioned in this part of the conversation. At the top of the list, Gothenburg was third (David cited 58% single and 55% divorced), London second (57% single), and Miami first. The panel pointed out that London was now both one of the worst and one of the best cities. David said the lists measured different things: this one only counted how many people were available. Someone added that Miami, with its many single people, is probably a hard market in its own way because people there are less inclined to commit.

David preferred a second, US-only list that combined three factors: availability of singles, rent, and the city's national nightlife ranking. Someone asked whether a 50-year-old looking for love cares about nightlife. David said the nightlife measure included restaurants and places to socialize, so it was about social opportunities more generally. Salt Lake City came third, with a median one-bedroom rent of $1,200 and a top-10 entertainment ranking. Knoxville was second and St. Louis was first. The worst cities on this list were Henderson, San Jose, Fresno and Bakersfield. David said three were in California, where he is from.

Matthew's reaction was that the more he heard, the more he wanted to "scrap the idea" that there's a perfect city for dating. Someone noticed that mid-sized cities kept appearing near the top. Another host said smaller cities also limit your choices, so they come with their own disadvantages.

16:59

Blaming Circumstances

Audrey compared the city debate to the way people talk about age. In your twenties, dating is the worst because no one is ready for a relationship. In your thirties, it's the worst because everyone is pairing off. In your forties, it's the worst because everyone left is damaged or just out of a marriage. She accepted that some ages and places really are better or worse. Someone looking intentionally at 28 has more options than someone at 60, and three dates a week beats one date every three months. But she thought people are prone to blaming circumstances and treating their own as the worst, and that they do this with cities too.

Matthew agreed that blaming circumstances is an easy place to go when you're frustrated. He still said being around a density of people helps, and that a very small place is harder. Audrey asked whether density still helps in places like LA or New York, where it can feel as if nobody is dating intentionally.

Matthew rejected that premise. He said there's no city on earth where people don't feel the pull toward a partner, and that in a city where you're "trying relentlessly to make it," many people think a loving partner would make life easier. He called the idea that everyone is too happy chasing careers to want a partner "not a reasonable analysis of human behavior." People pursuing a career aggressively often put it first, he said, but not everyone is like that, and values often change when people meet someone they really like. He accepted that more density means more competition, so you have to stand out, but he argued this is achievable by making the best of yourself.

He also said people should check their own behavior. In dense places, the belief that there will always be someone else makes people so picky that they don't invest enough in anyone to see how good they could be. They skip the second date or the extra conversation, and so "we can end up becoming that vibe ourselves."

20:51

City Loneliness and the Courage to Engineer Interactions

Matthew described a loneliness he thinks is particular to cities. You walk home past people spilling out of bars and restaurants, laughing with drinks in their hands, and feel that you haven't found your people or your person. Someone added that cities give you constant FOMO, so you feel you're inside the city but outside the experience.

Matthew said meeting people in a city takes a lot of courage, and that you have to "engineer interactions." For some people that means being willing to approach others more. He said he was never so confident that he didn't feel nervous approaching someone. Sometimes it went well and sometimes it didn't, and Stephen had been with him for both. When it went badly he felt stupid and embarrassed, but he had still done it. He said people need to keep that courage, especially if they don't want to be stuck in a city depending on dating apps because they no longer know how to meet anyone in person.

23:10

Approachability and Micro-Interactions

Matthew said a key point many people miss is that approachability matters as much as approaching. People are so focused on how to walk over to someone that they don't think about making it easy for others to walk over to them. Do you stand facing the wall, or facing inward at the bar, or do you position yourself so someone could easily start a conversation? Someone added eye contact.

He then described micro-interactions, which he said he's "very, very big on." People think of it as either talking to someone or not, with a huge gap in between. Matthew wants people to imagine "100 slices" between those two states that make it more likely you'll "tumble into" a conversation: eye contact, where you stand, asking someone what they're drinking because it looks good, clinking glasses with the person next to you at the bar, complimenting a bag, jacket or shoes. These small moves, he said, signal that you're open to talking, warm, and "not a person who's going to bite your head off." Walking across a room to talk to someone is a big move. His advice was to stop fixating on big moves you never make and to focus on low-risk, low-stakes interactions that tend to grow into something more.

Audrey added a tactic for bars and similar places: talk to lots of people as soon as you arrive, before deciding whether you find anyone attractive. You warm up, so when someone you're interested in does appear, talking to them isn't a huge leap after spending the night in your shell. Matthew said at that point "it's not a strategy, it's a way of being."

26:10

Pride, Routine and the Tourist Mindset

Matthew said pride is often the enemy, especially the longer you live somewhere. Over time people settle into a few friends and a few routines. The first time you walk into a coffee shop, it doesn't feel embarrassing to introduce yourself to the barista, ask someone's name, or ask the person next to you where else is good nearby. After a hundred visits, though, it's "my coffee shop" and you don't want to embarrass yourself, so people become "too cool to be vulnerable."

He contrasted that with tourists, especially young ones staying in hostels, who talk to everyone because they're only there for three days, have paid to be there, and want an adventure. They end up engineering new friendships or a romance. His explanation for why someone might find nobody at home in five years and then meet someone on holiday is that they "adopted a holiday persona."

Audrey agreed but said it's genuinely easier when you're passing through. Being only in town for three days gives you a cover story: you're not desperate, you're talking to everyone. When you live there, speaking to someone feels like it signals interest, and that makes you more nervous. Matthew said this is "only something in our head." His example was a restaurant owner who walks around asking diners how their night is going. Nobody knows the person owns the place, but they act as if they do, and people respond. He suggested adopting a similar story: resolving to make the most of your city again and treating it as if you're new in town.

29:30

Advice for People in Small Cities

David asked what people in smaller places should do. Matthew said to accept that you'll have fewer options, but to ask whether you're really making the most of the ones you have. Are you being brave with people at your coffee shop or local bookshop, and are you joining clubs? A small place means you won't meet new people on every corner, so you have to be more proactive: engineer social groups and community, and build a "tribe" on purpose of people who like what you like and value what you value.

Audrey's practical tip was to widen the radius on dating apps, and to include a larger city about an hour away if you're willing to travel. Matthew called this trading convenience for options. In New York you might only need a one-square-mile radius, but if you live upstate somewhere less populated, you may need a much larger one and to be willing to drive an hour for a date, which he said is "not the end of the world."

32:23

Listener Emails on Money: Paige and Dana

The panel then went back to an earlier episode, "What's behind the male fear that women only care about money," which had prompted two emails.

Stephen read the email from Paige, who described themself as a 37-year-old single woman living in Texas and a longtime listener. Paige said they were bothered to hear the theme repeated across several episodes because it seemed to validate the rhetoric of the far-right "manosphere." Paige wrote that they and their single friends are homeowners and financially independent. They invest, give to charity, look after their homes, and are generous with loved ones. None of them need a man who earns more than they do, or care much about how much a man earns. They're looking for equals with similar values. Paige's concerns were different: men who can't cook and spend a lot eating out ("Chipotle boys"), men who invest less well, give less to charity, spend more on hobbies and frivolous things, or are drifting toward a sports-betting addiction. Paige included links to articles on several of these points. Paige also wrote about the fear of ending up with a man who doesn't contribute at home regardless of income. Their points were that women who out-earn their partners still do more housework, carry the mental load, and seem to seek therapy more. Paige acknowledged the topic has much more nuance, including pay parity, social expectations and generational differences. They said they and their friends now talk about looking for a "partner" rather than a boyfriend or husband, and asked for a more balanced conversation in future.

Matthew said he loved the email. He said the panel may have given the impression that they were reinforcing manosphere stereotypes, but that they try to say the opposite: these are things people often claim women care about, and the claims don't match the women the team knows or coaches. He said some women fit the stereotype, just as some men do, and that the team has long prided itself on not reinforcing gender stereotypes. He would be sad to think they had failed at that.

He then read the email from Dana, who wrote that financial goals and lifestyle expectations clearly matter in dating, but that couples with similar means often run into serious trouble when their financial values don't match. Dana's examples were couples with similar salaries where one wants to save hard for a home while the other prioritizes travel or eating out, or where one wants to stay in an expensive city and the other wants to move to save money. Dana said such mismatches can cause as much strain as income gaps, or more.

Matthew called this a wonderful point. How we spend money shows our values, the lifestyle we aim for, and what we prioritize. Someone added that it also shows how we waste money, or whether we even consider something a waste. He argued that focusing heavily on income or wealth gaps distracts from differing values around money, which can cause just as much incompatibility. He added that if two people share values around money but have very different amounts of it, those shared values may be what makes them compatible despite the gap. He ended by speaking to men who worry they'll be overlooked for not earning enough: many women are looking for someone with the same money values, and that matters more to them than whether a partner earns as much or more.

38:44

Love Lifeline: Dating at 53 When Men Date Much Younger Women

The listener voice note came from Janelle, who is 53. Janelle said they're proud of their age and have no problem with it, but that men seem to. Men show interest, and then Janelle learns they're dating, or have dated, a woman younger than Janelle's daughter. Janelle sees a man around 50 who has dated someone in her twenties as a major red flag and finds it "gross," and asked whether that's too judgmental and how men think about it.

Audrey said she fully understood the reaction and partly agreed, but that the key question is whether it's a pattern. If someone consistently dates people 10, 20 or 30 years younger, she said, it's "kind of creepy," and she finds it strange to gravitate only toward that, if only in terms of maturity. One or two big age gaps mixed in with age-appropriate relationships is different in her view. People try things when they date, the relationship may have been mainly about attraction, and some older men feel their age heavily and feel younger dating a younger woman. Matthew noted that the team also hears from women in their fifties who enjoy dating younger men.

Matthew asked Audrey whether the size of the gap changes things: someone in their fifties dating someone in their twenties versus someone whose last partner was 35. Audrey said her view still applied. She repeated that she agrees with Janelle and would feel the same, but said people shouldn't be written off over one relationship. Anyone could look at a couple of our exes and wonder how we were ever attracted to them, so people should give each other grace. She said the way someone talks about it matters. Describing it as a somewhat embarrassing post-divorce semi-relationship that obviously didn't last is different from saying "my ex was 28 and there's nothing wrong with that." Her advice was to watch whether it forms a pattern and a profile of the person.

Matthew agreed that the pattern is the most important thing to look for. He also said how someone talks about why it didn't work out tells you a lot. He gave a hypothetical of a 53-year-old saying the relationship was fun and the attraction was real, but that the gap in life experience showed them how much they need deep compatibility with someone who truly understands them. Someone else said it would bother them if the younger partner was about the same age as the man's own child, and in that respect agreed with Janelle. Another person mentioned a couple they know who are married, one about 28 and the other in their fifties, and noted that the older partner has no children.

Matthew's own view was that each person has to decide what they value, and that dating someone from a very different generation says something about what you value. Maybe you're dating "the wisest 28-year-old in the world," he said, "but probably not." What looks like an old head on young shoulders is often a superficial maturity rather than the kind that comes from living through things. The younger partner also may not share your references or understand what your thirties and forties were like. He said it's fine for Janelle to find it off-putting and to decide such a person probably isn't for her. He also said people make "very human diversions." After a divorce, both men and women sometimes swing the pendulum and try dating someone younger, and he warned against condemning someone's character or giving them an identity based on one relationship, "within reason." What he would listen for is what the experience taught them, or whether they clearly thought it was great and would do it again without a second thought. He said how someone has been shaped by their experiences matters as much as, or more than, what those experiences were.

The team said they never hear voice notes before recording, apart from David who selects them, so the answers are given on the spot. They asked for notes of about 30 seconds.

50:14

"Steve Sleeves": Love Maps

The episode ended with Stephen's recurring segment, "Steve Sleeves." This time the game was "love maps": Stephen gave a scenario and the others named a city.

For the city you go to after a breakup, the answer was Paris, which the group said is always the answer on Netflix: a new outfit, a beret, and fluent French in about 60 days. Audrey mentioned watching the third season of The Summer I Turned Pretty, in which the heroine seems fluent in French almost immediately. Matthew complained about the show and then started watching it. When Audrey corrected someone's pronunciation of the Seine, she explained why she's careful. After a previous episode, listeners had criticized her for not remembering a French word. She speaks fluent French but left France when she was nine. Matthew said that kind of humility is how you know someone actually speaks a language.

For the city where you'd fall for the wrong person, the answers were Las Vegas, Miami as a party city for a fling, and Amsterdam, which one host tried to remember by describing it as the city people visit for drug tourism. For meeting someone completely different from your usual type, Berlin, for its rave scene and grungier, indie crowd. That led to jokes about the club scene and a "bondage rebound," and a quip that if you're already into that, you should go somewhere quieter and find a wine enthusiast.

For a fantasy meet-cute, the panel refused to give Paris another turn. They suggested Seattle, where you come in from the rain slightly steaming and meet someone in a coffee shop, and then a tropical Asian city where you duck into a cozy place out of the rain. When someone objected that you might not share a language, the others joked about learning fluent Japanese in two weeks and waiting outside the nearest izakaya.

Before signing off, someone mentioned that one of the lists had named Beijing and Mumbai as great cities to date in. No one on the panel knew why, so they asked listeners from those cities to write in and explain.