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I’m old enough to remember when some publication or other (OK, Forbes in 2007) declared that Pittsburgh was one of the worst cities for singles in America.
Let’s just say that it wasn’t the worst thing that had ever happened to us — that was when the Steelers lost to Tim freakin’ Tebow in the playoffs — but it was in the ballpark. For some, it was confirmation of dark suspicions. For others, it was a conspiracy (led by Cleveland, probably). For a few, it was a return to the bad old days of being a national punchline.
But who’s laughing now? Because a new survey says that Pittsburgh is the 4th BEST CITY FOR SINGLES — so Forbes can kick rocks. WalletHub has us a hair behind coffee/tech/rain mecca Seattle, then only Atlanta and Las Vegas. The score came from “35 key indicators of dating-friendliness” including “the average price of a two-person meal.” (WalletHub plays the clickbait game all too well but is at least fairly transparent about their methodologies).
What does this have to do with housing? Well, spending all your money on rent doesn’t leave much left over for dating, right? (My single days are long gone, but my advice to drink at home and skip dessert probably won’t get you many second dates.) Since we know that rents have skyrocketed everywhere, including here — but from a much lower starting point — then that sort of checks out. Maybe it would be a stretch to say that we’re objectively great. But when every other place is just a lot worse, that will have to do.
For sale: 2521 Spring St., Arlington, $120,000.
I wish I had some ideas for great date ideas in Arlington-adjacent areas, but Arlington is oddly isolated for being in the middle of a densely populated city. If we brought back the Brown Line — the long-dormant Hilltop connection for Pittsburgh’s “T” light rail — then you’d have more to work with. As it is, there are some nice places to eat in Mt. Oliver and Allentown. I’d suggest lunch at Echt Coffee House, not Alla Famiglia (a little pricey!). This cute little 1,000-square-foot Pittsburgh grandma house is charming, even though I’m not sure if that façade is really stone or some kind of inert industrial byproduct.
For rent: 131 W. 13th Ave., Floor 2, Homestead, $1,100/month.
Homestead is a place that seems to invite great optimism and pessimism, often on the same block, or when the light hits a certain way. It’s a good thing when a place is this affordable so close to major job centers, however, the hangover from losing a mill the size of Homestead Works (where my dad worked, as a teenager) isn’t something you can just shrug off. This brick triple-decker is especially useful and hard to build anywhere nowadays, so we have to hold on to the ones we’ve got.
For sale: 1017 Grand Ave., Woods Run, $129,900.
We like our street names literal in this part of the world — Grandview Street is on a street with a pretty grand view, right? This Grand Ave. roadway is probably named for, well, something else; maybe homes cost a grand when this house was built in 1907. $130,000 is still a bargain, though. That was the heyday of sturdy, compact brick four-squares with ample porches and windows, a combination that still works 100+ years later.
For rent: 218 Four Mile Run Rd., Greenfield, $1,000/month.
One of Pittsburgh’s most fascinating micro-neighborhoods is a wooded ravine below Greenfield and Oakland called “The Run.” If you’ve been there, it’s because you either ride your bike a lot (there are some good, secluded bike paths cutting through here) or because you need to eat at Big Jim’s in the Run once a year, just to feel something again (that feeling is “full.”). This house has two big red porches, and you know I have to commend it for that (you probably only get one, though).
For sale: 238 Alries St., Carrick, $75,000.
Put this in my personal ad: “If beautiful isn’t in my price range, weird will do.” What is even happening here? I was just in New Orleans and got to appreciate the appeal of the slim, long “shotgun shack” home — the closest thing I can think of to this. Oddly, this Cyclopean abode’s non-Euclidean geometry doesn’t seem to correspond to its oddly roomy interior — indicating, perhaps, some kind of wormhole to another reality where one would usually place a Pittsburgh potty.
For rent: Walnut Towers at Frick Park, 7070 Forward Ave., Squirrel Hill, $1,347/month.
This gigantic apartment tower overlooking the romantic, picturesque Squirrel Hill Tunnel is pretty weird. In fact, it seems to exist entirely out of spite; the attempts to bring another large apartment to the decrepit, abandoned Pittsburgh Irish Centre site nearby was met with a resounding fury from neighbors (and, well, the kind of nebby people who make obstruction their job). High-density housing in places people want to live, like Squirrel Hill, is good, actually. You don’t even need to go through the accursed tunnel most of the time.
This article appears in Dec 4-10, 2024.






