How does dating in a huge city like Chicago differ from a smaller city?
November 27, 2018 1:32 AM   Subscribe

I'm not quite sure how to ask this question, so bear with me. I'm single, in my 40s, in Portland OR, and I find dating to be relatively easy here [details inside]. I'm wondering if I've been in Portland so long that I don't realize it isn't that easy in other cities. Is dating harder in Chicago? What about Cleveland? St Paul MN? St Louis? How do I figure that out while researching other cities?

Here's some background for my question.

As a kid and a young adult, I moved a lot. By age 30, I'd lived in at least 21 homes in 15 cities in 6 states, 3 of which multiple times, not to mention living abroad. I've now been in Portland for over 15 years and I'm itching for a change, but I want someplace that could be long term. URBAN and affordable.

I'm in a perfect position for a major change. I'm single, renting, with zero debt and enough in savings for one heck of a big down payment on a home, but housing prices here have escalated to the point of absurdity, so buying in downtown Portland isn't realistic. Maybe that's not bad. I'm ready for a new adventure. I'm a freelancer and can do my job from anywhere (I'm staying in the U.S. though, so no foreign recommendations please).

I'm researching so many cities. Atlanta*, Baltimore, Chicago, Cincy, Columbus OH, Cleveland, K.C., Memphis*, Minneapolis/St Paul, Norfolk*, Philly, St Louis. I'm not kidding when I say I'm looking into all options. (*Probably not these, but I can't help being curious.)

My priority is living car-free in the heart of a downtown or hugely urban area. I cannot stress strongly enough: DOWNTOWN or hugely urban. I don't want to live near it. I want to live in it if not above it. Highrise life in the heart of it all makes me happy.

I'M AN URBANITE! The more urban, the more I'm interested... but...

...is too big TOO BIG for dating?

In 2018, how does dating in a huge city differ from dating in a medium sized city in various parts of the country? How does one even begin to figure that out?

Here's an example of what I mean.

Here in Portland, I wrote a story about how my couch (it's actually a loveseat) was sick of me coming home alone. I posted in online and met some really clever women. Fun! ...is it that easy in other cities?

I've met women for photo walks, where we treat the city like a visual scavenger hunt while snapping pictures. It's fun! I've met women for beer and board games at local pubs, where we create our own wacky ways to play well known games. Fiction Scrabble is awesome: you can only play fake words. In order to play a word, you have to pronounce it and explain what it means. RIDICULOUS fun! I once had a date pull Connect Four out of her huge purse, and she introduced me to Existential Connect Five, where three on one side can connect to two on the other side to make five, just like playing Asteroid or Pac Man at the arcade when we were kids. FUN!!!

I find it easy to meet women for that sort of thing here in Portland... but... if I moved to downtown Cleveland, is it a dating desert, even for a happy clever guy like me? Is it harder? If I move to near the Magnificent Mile in Chicago, is it too big and too urban to connect like that? Is St. Paul too small, with weather too harsh, even with the skywalk? Is St. Louis too... St. Louis? I don't know. Downtown St. Louis is so affordable, but is it a dating desert?

How do I even begin to figure this sort of thing out?
posted by Mr Ected to Human Relations (33 answers total) 12 users marked this as a favorite
 
I date in The Biggest City so I can't speak for places like Chicago, but there is a huge and toxic paralysis of choice/"trade up" mentality that goes on in the online dating world in NY. Everyone knows it and complains about it.

A huge portion of the dating population approaches dating with a one-foot-out-the-door-in-case-something-better-comes mentality. Another large portion approaches with a "I'm looking for a serious relationship, seriously! But also, I'm like...real busy" mentality. And another large portion approaches with a "I'm not looking for anything serious at all" mentality. These three groups are constantly clashing and failing at communication and pissing each other off hugely. Everyone deals with it so everyone's guard is way, way high so there is very little room for magical dating chemistry (not saying it's impossible, but it's common).

There are infinite options so dating apps usually mean 1-6 dates tops before one party ghosts or moves on. It is super easy to find a date and very difficult to keep any momentum going for above reasons. NY may be unique in this way compared to other cities because it is so much larger, so my experience might be moot, but that's my experience of dating in a large city.
posted by windbox at 4:10 AM on November 27, 2018 [13 favorites]


I don't think the Twin Cities are what you're looking for. Downtown Minneapolis might be heading in that direction--when I left four years ago there was increasing development aimed at drawing people to live in the city center. (New apartments; it was up to two supermarkets from zero when I moved there in 2008. On the other hand, I've heard the Macy's closed.) Downtown St Paul is even deader than downtown Minneapolis on the weekends (but, who knows, maybe it's had an awakening I don't know about).

I'm tempted to tell you to pick somewhere you like and dating will follow, but I have to admit that online dating (which sounds like what you've been doing and is the obvious option in a city where you don't have a social circle) has been different in different places for me. I can tell you that I knew a woman in Minneapolis who was making a determined effort at it and found the pool of acceptable men to be quite small (and the people she found online would often turn out to be friends of friends anyway), so, assuming you're a decent bloke, that works in your favor.

I'm also obliged to warn you about racism in the Twin Cities. I feel a bit, I don't know, hypocritical doing it as my anger has dissipated and it's hard for me to give concrete examples. (And I'm white and grew up in Chicago, so it's not like I should talk!) But when I moved to Austin (you really want a car there, don't put it on your list) and someone asked me about Minneapolis, 'racism' was one of the first words out of my mouth.
posted by hoyland at 4:20 AM on November 27, 2018 [2 favorites]


Wherever you go, there you are, right? It sounds flip, but your current dating experiences are likely to carry over into any other city.

I would advise you to look at other neighborhoods in Chicago, though, if it’s in the running; it’s a very urban and easy-to-navigate city, even a few miles out, and the “downtown” parts are paradoxically more boring because they’re full of offices and places for office workers to eat lunch. Mag Mile is where, like, the really big Gap is. It’s a subject for an entirely different AskMe, and one that I recommend really digging into, because Chicago is great.

I found it relatively easy to date in Chicago, if your definition is “find people to go on a date with” or “go to cool places on dates.” Anything beyond that, that’s up to you and luck.
posted by Metroid Baby at 4:31 AM on November 27, 2018 [7 favorites]


In general, I'd say most Midwestern cities (such as Indianapolis, Cleveland, Columbus) are not going to even come close to what you want. "Downtown things" happen occasionally, and people do live there, but there is nothing like the vibrant ebb and flow of life that you describe. I'd go so far as to say, you cannot live in these places without a car. There are just not enough "downtown" things to do, or people to do them with, at that level. Living downtown, or even very-downtown-adjacent, is just too expensive, for one thing. That's my 2 cents as a person with a decent level of experience in these sort of locations.
posted by I_Love_Bananas at 4:40 AM on November 27, 2018


A huge portion of the dating population approaches dating with a one-foot-out-the-door-in-case-something-better-comes mentality. Another large portion approaches with a "I'm looking for a serious relationship, seriously! But also, I'm like...real busy" mentality. And another large portion approaches with a "I'm not looking for anything serious at all" mentality. These three groups are constantly clashing and failing at communication and pissing each other off hugely. Everyone deals with it so everyone's guard is way, way high so there is very little room for magical dating chemistry (not saying it's impossible, but it's common).

There are infinite options so dating apps usually mean 1-6 dates tops before one party ghosts or moves on.


That pretty much sums up my online dqting experience in Philly!

Philly is a great city that ticks your boxes though. Definitely "urban", definitely doable without a car (i don't have one, or a license). It's also a great city if you like the arts, history, diversity, and progressive politics.
posted by bearette at 5:18 AM on November 27, 2018 [3 favorites]


I can speak to dating in St. Louis a few years ago, and the Raleigh/Durham NC area up to two years ago. (Happily, not dating anymore.)

Lemme preface by saying I love St. Louis, but if you want to live car-free I can't recommend it very strongly. You could live downtown or in U-City or in the Central West End (CWE) and survive with no car, but it's not really a city with great public transport. You're going to want to access All The Things(TM) and that means car.

You can find some nice lofts downtown for reasonable rents / prices compared to Portland, but St. Louis isn't really a huge skyrise city. It's got a few tall buildings, but not a ton.

I found dating in St. Louis to be easy in my early 40s, but didn't find "the one" there. But there's a pretty large population of people in their 40s (mostly getting out of marriages) and looking to date. St. Louis also has a good sex positive community. You'll probably find that dating in St. Louis is different than Portland. I noticed a distinct regional difference between dating in Denver in my 30s to St. Louis in my early 40s, and then Raleigh/Durham in my mid-40s, but it's hard to articulate it exactly.

But I wouldn't term St. Louis a "huge" city. It seems to me you will quickly find it feels like everybody knows everybody else. There's also a big county/city split, and I felt like I picked up on a strong divide between county dwellers and city dwellers.

There's a lot to do in St. Louis for folks in their 40s. There's a decent burlesque scene, lots of arts, theatre, decent music scene and most major acts will roll through St. Louis almost as frequently as they tour the coasts.

I don't know if St. Louis would be quite what you're looking for. It's a unique city with a lot to offer, but not really a huge metropolis. You might want to consider adding Denver to your list, but it's going to be a fair bit more expensive. But worth looking into.
posted by jzb at 5:37 AM on November 27, 2018 [1 favorite]


Chicago is fine for this. More than fine. The biggest issue with midwestern cities is that many people are lifers --- from there, stay there, only have friends from there. That's not a huge issue in Chicago because it has more inflow, but who knows re: cities like Cleveland. Good luck & enjoy.
posted by Rock 'em Sock 'em at 5:42 AM on November 27, 2018 [1 favorite]


Anecdata: I knew someone from Portland who lived in the Midwest for close to ten years and spent that whole time complaining that he couldn’t get a date because Midwestern women are weird. I was skeptical about this causal inference, but when he moved back to Portland he did indeed have much better luck with women, and is now married to one of the people he met back home. Good luck with your decision!
posted by eirias at 5:50 AM on November 27, 2018 [3 favorites]


If you use OK Cupid, it’s pretty easy to figure out where the largest pool of potentially compatible daters exists by changing your location for a week or three days or whatever to each of the cities you are considering, in turn, and seeing the results. It’s a fairly painless trial run. There is no science that will prove that the people on OK Cupid are a perfect match for the actual dating pool in each area but I do think it’s better than guessing. Good luck!
posted by Bella Donna at 6:07 AM on November 27, 2018 [2 favorites]


Chicago is fine for this. More than fine. The biggest issue with midwestern cities is that many people are lifers --- from there, stay there, only have friends from there. That's not a huge issue in Chicago because it has more inflow, but who knows re: cities like Cleveland. Good luck & enjoy.

I did actually find Chicago to be like this, at least compared to cities with more turnover like New York (and, I'd guess, Portland). Yes, lots of people do come to Chicago from other midwestern states, but the overwhelming majority of them move there right after college and then become "honorary lifers." If you're moving there in your 40s, the pool of people your age who are not already ensconced in long-established social groups will be quite small.
posted by enn at 6:14 AM on November 27, 2018


Big cities gonna big city... dating in NYC, Chicago, Philly is just going to be harder, primarily because there are very few consequences for ghosting people or generally being kind of not nice, since you usually will not know the same people, unless you run and also date in small scenes.

I have to say though... you're coming from a uniquely bizarre place. Portland is so tiny. I know it's really not, but I lived there for 2 years and constantly felt like I was tripping over the same people again and again. Plus, it's very close to uniformly... quirky? You're going to find a much bigger range of personality types in a really big city.

As for urban and affordable... you don't have many options. Don't even joke about moving to St. Louis, Cleveland, Atlanta... you will be miserable. Then again, if you think Portland fits your criteria, maybe you would be okay. There are like, 3 American cities that are actually walkable.
posted by Automocar at 6:41 AM on November 27, 2018 [4 favorites]


Downtown Columbus isn't a dating desert because, well, it's just not big enough. It's really only a handful of city blocks. Nobody lives there, but it doesn't matter, because neighborhoods where people do live are so near. Like, Victorian Village, German Village, and Franklinton (three of the most common neighborhoods for singles) are just a five-minute walk across the respective bridges. People who live downtown (all three of them) are closer to people in the southern part of Victorian Village than the people in the northern part of Victorian Village. Furthermore, since so little occurs in downtown Columbus after 5pm, you'd be spending a lot of free time in those neighborhoods anyway. You shouldn't have any problems meeting people, but I will say that, in 20 years of living in Columbus, I don't remember ever meeting a single person (not just in terms of dating - I'm talking socially, professionally, everything) who lived in actual downtown.

Something you might want to consider: Because of a quirk of the history of St. Louis, there are actually a fair number of high-rise buildings and a bit of a downtown-y feel in the suburb of Clayton. I strongly doubt that's what you're looking for, but it's an option. If nothing else, you could get a wonderful view overlooking Forest Park, which is really the only reason to ever consider living in St. Louis.

For reference, downtown Clayton (which, to reiterate, is a suburb that's basically a tax dodge) has a similarly-sized downtown to Columbus, which is the 15th-largest city in the country. Downtown Columbus is probably not what you imagine when you think of "urban".
posted by kevinbelt at 7:11 AM on November 27, 2018


This is an excellent question. I’ve lived all over the U.S., visited 46 of the 50 states; the only exception being the Pacific Northwest, Alaska, & Hawai’i. So, obviously, you’ll know more than I will about Portland. I currently live in NYC, to give you context.

That said, right off the bat: if you want urban and affordable, about the only two places I can think off that fit those criteria are Philadelphia and Chicago. If I were in your shoes, I’d pick Philly over Chicago for two reasons:

- it’s nicely equidistant between New York City and Washington, DC; about 90 minutes (by train, more by car) away from both of those places. It’s entirely possible to swing working remotely in NY/DC and living in Philly. Absolutely lovely city, it’s cheap, it’s urban.

- Chicago will absolutely have much more of a “lifer” component than Philly will. Chicago is basically the Midwestern metropolis; people come from elsewhere in the Midwest to land in Chicago, much the same way that people come from elsewhere to land in NYC/DC. But even so, there’s much, much more of a native contingent in Chicago than there is in other cities. Especially if you’re in your 40s, it’s going to be difficult to be the “newcomer” in a lot of social circles. Love Chicago, but it’s easier to be a new person in Chicago in your 20s and 30s than it is in your 40s.

NYC and DC have a constant churn of people coming in and out, which makes it way easier to be the new person in those towns. With NYC, it’s the various industries (whether that’s news, entertainment, finance, service, what have you); with DC, it’s politics. Chicago doesn’t have that, in anything like the volume NYC and DC have. Hence the lifer component.

I grew up in Columbus (outside of it, actually); I’ve got a soft spot for it, occasionally consider moving back, and then I dismiss it. If you’re looking for affordable, it is; it is, however, not at all urban, not even close. Same goes for a lot of other places on your list — KC, Memphis, Cincy, to be exact. Lovely cities, not what I’d consider “urban”. Baltimore is affordable, I like it, but if I were picking between Baltimore & Philly, I’d pick Philly; it’s a better, bigger Baltimore.

Norfolk is not urban; unless you’re all about living in a military town, I wouldn’t consider it.

Like other people have said, the big issue with a lot of the places you mention in your OP is that they’re the kind of places that it’s hard to be a “new” person in. They’re basically very large “small towns”, and unless you’ve got history in the area, it’s gonna be hard to break into the social circles. Like, I’ve got deep and abiding love for Cleveland, but I’d seriously question anyone who willingly chose to move there in their 40s. People move away from Cleveland, not to it!

I love Denver, but it is no longer affordable, and if you’re a man, there’s a reason one of Denver’s nicknames is “Menver”; it’s because there’s more men than women in Denver. Which shouldn’t dissuade you, but if you’re a straight man, it’ll make dating more difficult, just from a numbers game perspective.

Bottom line, up front: move to Philly. It’s got what you’re looking for in terms of urbanity and affordability.
posted by arkhangel at 7:55 AM on November 27, 2018 [1 favorite]


Norfolk should definite be out of the running. You would definitely need a car.

I would add 2 other cities to your list: Boston and Nashville.
posted by sudogeek at 9:18 AM on November 27, 2018 [1 favorite]


You can definitely live in downtown Philadelphia and never feel the lack of car. Easily.

I think people are jumping to conclusions about what "good dating" means to you. Yes, in a bigger city like Philly there are more people who will ghost or generally dip out rather than enter a relationship. That said, from your post, it sounds like what you enjoy about dating is meeting a lot of new people and doing fun, quirky activities with them. You can 100% do that in Philly.

Aside from a huge vote for Philly, I'll vote against Baltimore. It's really hard without a car, and even in "the thick of it" there isn't that much... it.
posted by telegraph at 2:21 PM on November 27, 2018


For those who recommend Philly, can you recommend specific neighborhoods - the more urban the better.

For Chicago, I'm primarily interested in the area around the Magnificent Mile, from Marina City to the south part of the Gold Coast.
posted by Mr Ected at 2:58 PM on November 27, 2018


Philly is pretty much all urban; the Northwest and Northeast sections are more far-flung and residential but still accessible by public transit. NW Philly has beautiful green neighborhoods. Germantown and Mt. Airy in NW are standouts, IM0, but maybe not first choice without a car (although I lived in Mt. Airy carless and it was fine).

Beyond that, it's kind of a matter of what neighborhood you like. They all have their own unique characteristics. Certain sections are high crime, but that will be pretty obvious. Each neighborhood has its own unique characteristics and there are lots of neighborhoods, all urban, so I won't go through them all. I could get more specific if you can give some ideas on what you're looking for specifically in a neighborhood (demographics, vibe, etc), other than not needing a car.
posted by bearette at 5:19 PM on November 27, 2018 [1 favorite]


I moved to Chicago from NYC on somewhat of a whim (my business partner's whim) on a week's notice not knowing anyone or anywhere. I have no regrets. Greatest decision of my life other than a few regarding my family. I met my wife in Chicago. She is from Buffalo (and an ex-wife now). I found dating in Chicago much easier than in NYC. Maybe because I did not know anyone. In NYC, it was full of oh you grew up in Dix Hills, did you know... In Chicago, while I agree that there are a lot of lifers and I eventually became good friends with a clique that grew up on the North Shore, I think many women were sick of dating the same old trader who went to midwestern big 10 university and grew up in Deerfield or wherever. I was a novelty. You will be too. (I have several female unmarried friends in their 40s in Chicago now who would love to go on a date with a creative, upbeat fun type like you claim to be.)

If I were in my 40s and moving to Chicago as a single person, I would live in a high rise in the Gold Coast. It is right near the Mag Mile, near downtown, near culture and near a nightlife such as Hugo's/Gibsons on Rush St and the restaurants around there.

I miss Chicago. Favorite city including my hometown city of New York.

Other cities I would consider would be Pittsburgh, Cleveland, Philadelphia and Charlotte. I agree with a responder above that you are who you are, and you will have dates that you want and that you like no matter where, but there are certain places that are easier than others.

I have sort of a romantic nostalgic ignorant vision of living really cheaply in a really nice rust belt city. I think you would thrive in one. As for Philly, I have a best friend that went to Penn undergrad, Penn Medical and did their residency at Penn. They still live in Philly area. They LOVE it. My nephew in his late 20s lives in Philly with no car and dates a lot. I follow his Insta and I am amazed at all the dates he has and the varied things he does on those dates.
posted by AugustWest at 5:24 PM on November 27, 2018 [1 favorite]


"If I were in my 40s and moving to Chicago as a single person, I would live in a high rise in the Gold Coast."

That's very tempting. I'm looking at the area, though I'm more drawn to slightly south, closer to or in the Mag Mile. But the Gold Coast sure is tempting.


"Other cities I would consider would be Pittsburgh, Cleveland, Philadelphia and Charlotte."

Where I'd want to be in Pittsburgh is out of my budget (downtown). I lived in the Burgh back in the 90s though, and my only regret is that I lived close to but not right in downtown Pittsburgh. What a great downtown.

I am all about downtown life. Not near it, but in it. Big city or small town, I love it all so long as I live right smack dab in the heart of it all. Not nearby, but right there in the hustle and bustle. I love the feeling of walking out my front door and being in the heart of it all.

Downtown Cleveland is compelling. The only thing it's missing is shopping, but it has two grocery stores, lots of pubs and restaurants, and the Playhouse Square theater district, all downtown. Very compelling. And affordable.


"I have sort of a romantic nostalgic ignorant vision of living really cheaply in a really nice rust belt city."

That's part of what keeps Cleveland on my list of maybes. I love the idea of being part of the rebound that downtown is going through.

I know I could do downtown Cleveland without a car, and Chicago is easy without a car... but are dates going to want to come downtown? One thing about downtown Pittsburgh I'll never forget is how it can be a nightmare to get in and out of, traffic wise. I still love it though!


Anyway... I appreciate all of the responses. You're giving me a lot to think about.
posted by Mr Ected at 6:50 PM on November 27, 2018


Big picture: This is like the third question you've asked along these lines (investigating life in other "big" cities), so I'm gonna suggest that you take advantage of your savings and work flexibility and visit at least a few of these places. And, frankly, for the midwest/northern cities, you should visit us NOW or in like Jan and Feb, because I'm not sure you really grasp how the snow affects daily life. Seriously - take a week, grab a downtown hotel (and rates can be relatively cheap in winter), wander the cities without a car, see how easy or difficult it is to get around without one, observe where people are when and why, find some cool things to do and think about how often they happen and how much they cost and how easy it is to get to where they're happening (and back home again . . . . )

I think you've got a bit of a romanticized notion of "big cities" (and, for the record, Cleveland is actually smaller than Portland, both the city proper, and the greater metropolitan area), where, like, you're gonna wander out of your downtown high rise condo at 1 pm on any random Saturday and BOOM! teeming mass of interesting people going interesting places and doing interesting things within a few blocks. Which is not necessarily the case - lots of downtowns are still recovering from decades of economic and social factors where the urban center is a place you go for work and certain special occasions (sports, concerts, live theater, dining) but mostly people live and socialize on the fringes of or outside the city. Or in small neighborhoods that are definitely urban but not downtown.

As far as doing fun interesting stuff for dating goes, well, *shrug*, pretty much all cities have lots of cool interesting people doing fun interesting things - that's why they're cities and that's why people live there (more or less . . . ) So I dunno that you should worry so much about that, but be more concerned with the livability and "vibe" of a city and whether it hits your criteria for weather and cost of living and etc. Once you're there you can find the fun interesting people to date.

Specifically: I had a whole thing written about how I still don't think downtown Cleveland is quite what you hope it is, but on seeing your most recent comment it just reinforces my first point - internet comments are no substitute for your own eyes and ears. Come on out for a visit, check us out. Maybe I'm wrong, maybe our downtown pushes all your buttons, in which case, *shrug*, Hey! Welcome to Cleveland! Maybe you'll find a different neighborhood in Cleveland that you like, maybe you're more patient than I am in dealing with our public transportation, whatevs. And even if the CLE isn't quite what you're looking for, hell, we can be a fun place to visit. (Again, though, do it while snow is on the ground. You've spent 15 years in a place that gets like 3 inches a year - 3 feet a year is a whole different animal.)
posted by soundguy99 at 7:05 PM on November 27, 2018 [4 favorites]


"I'm not sure you really grasp how the snow affects daily life."

I've lived in Pittsburgh. Twice. I grew up near Scranton. I went to college near Erie, where we often got lake effect snow daily. As a former skier, I know snow.


"Big picture: This is like the third question you've asked along these lines"

Yup. I'm probably going to ask a few more. I'm not in any rush to move, so I have lots of time to do research, which includes visiting potential cities, but it makes no sense to start visiting places before narrowing down my list. I'd tear through my entire savings trying to spend time in places a bit more research would have led me to cross off my list... and that's why I'm doing that research first.


"As far as doing fun interesting stuff for dating goes, well, *shrug*, pretty much all cities have lots of cool interesting people doing fun interesting things - that's why they're cities and that's why people live there (more or less . . . ) So I dunno that you should worry so much about that"

Yeah, but it's different in different parts of the country, which is why I asked. I've also lived in Florida and Texas. It's very different there, partly culturally, and partly because sprawl city life is so different than more compact or dense city life, which leads to differences in where or how far people are interested in going to meet.
posted by Mr Ected at 7:44 PM on November 27, 2018 [1 favorite]


For Chicago, I'm primarily interested in the area around the Magnificent Mile, from Marina City to the south part of the Gold Coast.

I mean, if you want to be where everything closes by 8pm and nobody ever wants to go there unless they're going to happy hour after work, and drinks are $14 even though they suck, and definitely none of the bars have Connect Four, then go for it? But I would NOT call that a good spot to try and date. But then again I also wouldn't call it a good spot to...anything.

What you want is Logan Square.

source: am an artsy-fartsy creative-career woman in her late 30s, have lived in Chicago my entire adult life, would absolutely never go downtown for a date. Are you kidding? This is Chicago, my entire 6-year relationship happened because we lived near enough to the same bar that neither of us had to get on a train.
posted by We put our faith in Blast Hardcheese at 8:07 PM on November 27, 2018 [3 favorites]


(I recognize that I may be a data point in the "Midwestern women are weird" category)
posted by We put our faith in Blast Hardcheese at 8:16 PM on November 27, 2018


If you need to be literally downtown and step out the door into the middle of hustle and bustle and crowds, well, you won't find all that much of that in downtown St. Louis. The closest thing we have, off the top of my head, is perhaps the loft district on Washington Avenue. I've had a couple friends who moved over there and liked it. But if it doesn't have to technically be downtown, the Central West End, which is still in the city, might do it for you, as it has a number of high-rises, it's walkable, and it's full of restaurants and cultural stuff and people all day and night long. Downtown Clayton could also do it for you, and it's a MetroLink ride away from the sometimes-bustling, walkable portions of the Central West End and downtown St. Louis. But I'm not sure it's bustling in the way you might be thinking if you've walked among the crowds somewhere like New York City or even downtown Austin, Texas. Would highly recommend trying before buying.

Other areas that are a bit more bustling and have a larger single population, like South Grand, Grand Center, the Delmar Loop, and Maplewood, in general have a lot more students and bohemian twentysomethings (or twentysomethings who prematurely behave like fiftysomethings) than you might be looking to be around. It can get a bit obnoxious. None of them have a lot of high-rises that aren't dorms or other student housing. The friends I know who have moved to the South Grand area have loved the walkable food and bar scene but I don't think have been so in love with the car culture or the detached loneliness of single-family rental houses and duplexes in the city. And you know how somewhere like New York City, if you live more than a 30-minute train ride from your friends or would-be dates, you'll never see them? Same deal here, only with cars—if someone has to drive more than 30 minutes to see you, or you don't have a car to meet up with them, they probably won't see you very often.

I think St. Louis has a lot of people who are interesting, geeky, clever, and involved in the arts in the ways you describe finding in Portland. The nice thing about a city like this is that there are no expectations, your money will go a long way, and so many cultural attractions are free or very low-cost. We have tons of great restaurants and bars. But you will want a car before long, and you will likely end up dating a lot of folks who have never left St. Louis and have no intention of leaving St. Louis (yet who, if they get serious and want to have kids, if that's at all in the picture for you, will then immediately want to leave the city for the county for reasons of schooling).

I feel like you aren't necessarily looking for St. Louis, but maybe something more like Chicago. But if you think anything in my first paragraph sounds intriguing, get an Airbnb here for a week and try it, and/or switch your city on OkCupid for a week.
posted by limeonaire at 8:23 PM on November 27, 2018 [1 favorite]


What about Madison or Milwaukee? (I haven't lived in either, so these may be insane suggestions, but they're definitely vibrant cities.)
posted by Threeve at 8:48 PM on November 27, 2018


"If you need to be literally downtown and step out the door into the middle of hustle and bustle and crowds, well, you won't find all that much of that in downtown St. Louis. The closest thing we have, off the top of my head, is perhaps the loft district on Washington Avenue."

For St. Louis, I've been primarily looking near 9th & Olive ish, and even more along Washington Ave near Tucker, which isn't downtown but it is directly above an active entertainment district (if I'm not mistaken). That loft district is shocking in terms of how nice yet affordable it is. St Louis is lower on my list of maybes, but it's definitely on the list that I'm continuing to research.

Thank you so much for the info!


"I feel like you aren't necessarily looking for St. Louis, but maybe something more like Chicago."

My fear with Chicago is that it might be too big. I've visited, but never with the thought of living there, so my knowledge is more that of a tourist.


"What about Madison or Milwaukee?"

Milwaukee is on my list. They just got a streetcar, and the East Town/Historic 3rd Ward district sure looks interesting. West Town might be too. I've never been there though, so I'm just researching so far.
posted by Mr Ected at 8:55 PM on November 27, 2018 [1 favorite]


I haven't lived in STL in a few years but just want to mention - "That loft district is shocking in terms of how nice yet affordable it is" - The reason for this is it's absolutely dead after work hours. I have a lot of love for STL and I'm actually moving back in a couple years, but if you want carfree urban hustle and bustle, STL ain't it.
posted by saul wright at 6:04 AM on November 28, 2018 [1 favorite]


I live in Philly right now after living in Chicago for four years, and can affirm everything people are saying—it really is comparable only to Chicago AFAIK in terms of the combination of being a real, serious city (in really every way) and being affordable.

In terms of neighborhoods it probably depends on both budget but also whether you want to buy or rent. It sounds like you are interested in buying: how much space do you need? Rowhouses in Philly usually range from 1000 sq ft. on the small end to 2000, and the price for a liveable house from 200k to 400k depending on neighborhood, build, etc. etc. As I will explain below, condos are a little more mysterious to me, but I get the impression they are comparable. Definitely rent for a bit or visit extensively before buying, it is a city that demands experience and knowledge.

Philly has a fairly unique situation compared to other cities of its size in that more people buy small houses rather than live in high-rises, even in the denser parts of the city. The only area that I'm aware of where people live in big high-rises like you are saying is the Rittenhouse Square / Center City zone. There are a few well-known buildings whose names I can't remember off the top of my head (the Phoenix Building, etc.), and I've heard that those who live in them really enjoy it. It will feel very much like a bustling downtown, but I would say much nicer than its equivalent in NYC / Chicago, primarily because it is much more compact, kind of like if midtown, the Upper West side, and the Upper East Side were all jammed together.

All that being said, if you are interested in classic Philly rowhouse-land (which is really the most common options) there are some great high-density, car-free areas to consider. Look into Queen Village (some of the most beautiful old houses but might be too expensive), Fishtown (a little too cool and overpriced IMHO but the classic hipster neighborhood here), and really anything South Philly down to Snyder Avenue and near the Broad Street Line (one of the two big subways). I would say especially east of Broad (Passyunk, Dickinson Square) might tick your boxes, although I would say those areas are probably best if you are comfortable on a bicycle; parking is a nightmare but they are just a touch far from other neighborhoods.

We just bought a rowhouse and ended up in West Philly, on the northern edge of a large neighborhood called Kingsessing. West Philly in general is a mixture of student-oriented (especially north of Baltimore and out through the 40s) crunchy/professor-y around Baltimore, and middle-class African-American from the 50s to the border of the city. It's one killer edge is that it has a great and to my mind well-functioning trolley network that can zoom you into Center City. It was one of the main reasons I moved where I did, because in Chicago I lived in Hyde Park and wanted to avoid that kind of feeling in the future.

The really great thing about Philly (other than its obvious affordability) is that it has all of the amenities of a city like Chicago (probably not like NYC, just isn't enough money or people for that I think, NYC is really really really in a class of its own, but of course, you can go for the day from here!) but is much more compact, especially in terms of the urban-feeling areas. It has suburban-ish neighborhoods that stretch for miles (seriously) but you can go from one cool thing to another by bike or public transportation in about a half-hour. I have a car but like half of the city drive it once a week for the following things: roadtrips; parks (check out the Wissahickon, it's amazing); and groceries. That brings me to a big downside: although it's improving fast, Philly's grocery game can't touch Chicago's. I lived in the neighborhood of Edgewater and could bike w/in twenty minutes to three spectacularly high-quality grocery stores; in Philly, it just isn't the same. I drive to Netcost, a massive Russian supermarket in Northeast Philly, every few weeks, and minorly gripe otherwise as I go to either the Co-Op (OK produce) or Whole Foods (which is like every Whole Foods). I think this might change but honestly I also think a great grocery store needs a deep history and well-developed connections to wholesalers etc., so I'm not holding my breath.

Milwaukee is... I don't know. Someone must like it, it just gave me a weird feeling the one time I visited. A weird kind of edge. Someone mentioned Madison, which is one of my favorite small cities but probably needs a car.

I was married even before Chicago (and didn't even use apps before I met my partner) so I can't speak to that. Dining out indicates that the Tinder date and its weird conversational rhythms are alive and well in the gastropubs of Penn's City.

Really the more I write this the better Philly sounds. The only downside for most people is that they don't have a job here, so if you can freelance, it's sort of the obvious choice. I'd love for there to be other Phillies out there, and there are lots of great small cities in America that aren't on people's radar, but that combo of being big, well-connected, affordable, and walkable? Just not seeing it elsewhere.

Apologies for the length, but hope this is helpful to you or someone else.
posted by Stilling Still Dreaming at 7:06 AM on November 28, 2018 [3 favorites]


"It sounds like you are interested in buying: how much space do you need?"

I love small spaces. A 500 to 650 square foot open layout is ideal. My current loft is 580 square feet, and it's more space than I need (not complaining of course!). My previous loft was one open room, 18x20, plus a bathroom & closet. Maybe 460 square feet? LOVED IT.

I'm looking as high as $225K, but only if taxes and HOA are very low (to balance out the higher mortgage). Most of the spaces I've been considering are in the $180K range, putting over a third of it down (maybe a bit more, maybe less, depending on the situation).


"Apologies for the length, but hope this is helpful to you or someone else."

Oh, no, thank you for taking the time to write that! I appreciate it!
posted by Mr Ected at 12:36 PM on November 28, 2018


I've spent some time in Madison recently, with a friend who lived there, downtown. You can get around pretty easily by bike, but I don't think there's a grocery store downtown. It feels a lot smaller than Portland. Car-free would probably be a challenge. My friend, a guy in his now mid-40s, dated a lot there, and felt like it was a pretty small place. And he also commented that he felt like midwestern women were a bit more conservative socially. Not weird, exactly, but maybe more traditional.

The dates you are describing sound very Portland-y in that sense that we tend to embrace our quirkiness here. So in a different city, you might be able to do some of those same kinds of dates if you initiate them, but I'm wondering if you're what enjoying here is the part where we let our freak flags fly.
posted by bluedaisy at 12:37 PM on November 28, 2018


Ok, if you are happy with small spaces them definitely look into condos in center city, you might find something in your budget. You could also keep an eye out for very very tiny trinities (3 story small houses) around Washington Square. Rare to find one at that budget I think but if you do it would be amazing, not least because it will be a real 250 year old house.
posted by Stilling Still Dreaming at 4:04 PM on November 28, 2018


Also, feel free to send me a message if you want a realtor rec or anything more detailed!
posted by Stilling Still Dreaming at 4:05 PM on November 28, 2018


For St. Louis, I've been primarily looking near 9th & Olive ish, and even more along Washington Ave near Tucker, which isn't downtown but it is directly above an active entertainment district (if I'm not mistaken). That loft district is shocking in terms of how nice yet affordable it is. St Louis is lower on my list of maybes, but it's definitely on the list that I'm continuing to research.

Ah OK. Well, the intersection of Ninth and Olive streets is indeed downtown. Depending on which side of Washington Avenue near Tucker Boulevard you're looking at, that might be downtown too. West of Tucker is only not part of the Downtown neighborhood on a technicality. It's part of Downtown West, which is basically the same thing. See the city of St. Louis' neighborhoods page.

Anyway, as saul wright mentions, "active entertainment district" is a bit relative. The other areas I mentioned seem to have more people around at night than I think Wash. Ave. does. But yeah, absolutely, the price is right here!
posted by limeonaire at 6:15 PM on December 1, 2018 [1 favorite]


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