...I live in an older community in the burbs, which I chose because I wanted a big organic garden to grow thing to share more than I liked the city. My neighbors introduced themselves to me with homemade treats. On holidays I do the same for them. We talk to each other, share things. We've build a community in the burbs. Maybe it's different in the McMansion areas, I don't know. But where I am it's community, sharing, little cars. A good place.

When my (ex-) wife and I bought a house together around San Jose, I was panicked for at least the first year about the mortgage payments versus our salaries, like, ohmygod, what have we done? But then she and I both got raises, and got raises again the next year, and after awhile the mortgage and taxes weren't a big deal. Now the house, which she still lives in, is worth 3x what we paid, and she's in good shape for equity.

When we split up, I couldn't handle the idea of yet more time in the suburbs and worked my way into a loft in San Francisco, and it's great, best place I've ever lived, about as urban as you can get. It would never have worked for her, though - she likes the safety and quiet of the 'burbs. It would have been hard to choose another place to live together that satisfied both of us.

As much as I like city living, though, there's a lot I've given up- no good place to barbecue, no garden space or options for fruit trees, no parking for guests, no storage space for bikes and stuff. I'm envious of a friend of mine, still in the 'burbs, who's able to throw casual dinner parties and have people just show up and have parking.

I recommend that the LW try to slow down a little to match the pace of the home ownership process. Give it a year or two and let the current real estate craziness bubble on for awhile to see if things pick up again, like they always have before. Think about this from an experiential, timing, and change-management viewpoint- yes, there's surface BS that makes living in a big house in the suburbs seem kinda odd, but there are a number of experiences you can have with it that can be kinda cool- the aforementioned gardening and trees, a yard for a dog, space and a yard for kids if he's so inclined. What could he do with the house now that would make it a cool place to live (for him or someone else) in 5/10/20 years? What can he do with the space? Maybe use it to throw great parties, or for meetings on interesting / worthwhile subjects.

Re timing and change management, the LW could look at all the changes he's gone through over the last couple years and decide that a bit of stability could be a good thing for awhile. Moving is stressful and disruptive. Rather than adding yet more change, maybe it would make more sense to hang out and let everything settle in for awhile. Don't give up the idea of moving somewhere more urban, but look at it from an optimal timing viewpoint. Your soul is pretty durable- it can take a bit of discomfort, as long as you don't let it go on forever.

I've never found that any place I've lived has sucked me in and glued my feet to the floor, including where I'm living now. Hang on to the idea of "what's next?", but look for a better set of indicators saying, OK, let's do something else now, than the panicky feeling that can happen within the first few months of new home ownership.

I tried the city, bought a very nice, quite expensive really, condo in Washington DC. It sure wasn't what Cary described! I had Saudi neighbors who beat their wive(s)? regularly, so I called the police on routine basis. A nice health club was nearby, but it was always crowded, unless I could get there at 5am or 10pm. Sure the coffee shops and musuems were great, but I didn't live in any of those places. The metro is great, but costwise more expensive than driving to my work. Oh yes, let's not forget public services. The schools there looked like they were from the developing world, and 911 actually put me on hold one night. City life? Ughh.

Unfortunately, the LW's sense of self seems to be tied to his surroundings.

But is he really "not himself" unless he's wearing skinny black jeans, carrying a latte, and stepping over winos on the way to work? How could that be?

Basically, it's ridiculous. It's also ridiculous that the LW sees himself as a victim of a decision he didn't make----except he did.

Own it, LW: you made the decision to move there, and to work for a hedge fund, and your wife likes it. And you're getting old. Maybe it's time to acknowledge that and deal?

Why not try start by rejecting the false idea that you are defined by where you live? It's sure to make you miserable, eventually, anyway. For example, what are you going to do when you get old? A 40 or 50 year old wanna-be hipster stuck in his own past is the definition of path-e-tic (rolls eyes).

If you stopped stereotyping long enough to check it out, you might find some pretty cool people are living in the burbs.

Throw a block party and get to know your neighbors, set up an organic garden in your back yard, xeroscape your front yard, volunteer to organize soccer or hockey games after school at your local park (there's always a neighborhood park in the burbs), etc.

Oh, and like others say, have some kids and your views will change. I used to live in the urban core, but now I'm living in a close-in, older burb. I'm really really glad my kids don't have to get mugged periodically like I used to, the schools are decent, and my kids love mucking about in our little back yard.

I also enjoy my eccentric neighbors....the policeman, the special ed teacher, the coot who grows heritage tomatoes and leaves piles of them on everyone's front steps whether they want them or not, the performance artist (you know, they have to live somewhere!), the anglican priest & his wife & family, the Somali immigrants whose kids are the only ones in the family that speak English, the guy whose hobby is demolition derby racing (its hard to miss the wreck(s) in his driveway, and parked all up and down the street), etc. Also, there is this older lady who dresses up life-size dolls and sets them up in seasonal dioramas in her front picture window (OK, I haven't gotten up the nerve to knock on her door yet, but honestly, it is surreal)