Where to go on a first date in Pittsburgh?

February 5, 2013 2:39 PM

27 year old straight male living in Pittsburgh. I'm doing the OkCupid thing. I would like to go on a few dates, but I don't know where to go for a first date. Elsewhere on AskMe, people have said that a first date with someone you met on Okcupid should be brief compared to a first date with someone you've known in person for a while. Makes sense. I could put together an awesome date that was three hours long, but when I try to think of something short and sweet, I'm at a loss.

Moved to Pittsburgh and worked in a kitchen in Southside for three years before getting my current 9-5 I.T. job a few months ago. Most of my Pittsburgh friends are cooks there. My social circle is very into deep-fried anything, and copious amounts of booze and weed.

My stereotypical 90%+ OKC match is an artsy/geeky, vegetarian(ish) grad student who studied in Europe for a semester. In an alternate universe, I would be too, so it makes sense.

Where are the quirky little places to grab a quick bite to eat that I would know about if I went to CMU or lived in Lawrenceville or something?

posted by UrbanEye to Human Relations (18 answers total)

I don't do the OKC thing, but one of my best friends does, and she says her first OKC meeting is always, ALWAYS at a place where you pay up front rather than waiting for a check. (Usually it's at a coffee shop rather than a restaurant.) That way you avoid any awkward who-pays negotiation at the end, and if you're not feeling it you can just say "Well, it was nice meeting you!" and leave rather than having to wait around for the bill.
posted by KathrynT at 2:42 PM on February 5, 2013 [11 favorites]

Apparently I did OKC wrong, then. I'm a 27 year old chick living in Chicago. My dates (there have been few, but successful) were all long, and involved meeting at a museum and then afterwards going to dinner at ethnic restaurant of my choosing.

Why? Because that's what I like to do. If someone is showing obvious signs of distress at being in a museum for a few hours, we will not get along. If someone is showing obvious signs of distress at eating in a hole in the wall taqueria, we will not get along. The date itself was a second layer of, erm, applicant screening, so to speak.

I will note that it was agreed upon beforehand (through messages/texts) that since it was sort of an all day thing, if at any point one person had lost interest, they were free to bail without making up an excuse, no harm no foul.

YMMV, but this is the process that has worked for me, and next time I'm back on OKC I intend to stick with it.
posted by phunniemee at 2:49 PM on February 5, 2013 [6 favorites]

Coffeeshop. Low key, public place, easy to escape if needed, also easy to extend the date if needed (just keep talking!).
posted by zug at 2:58 PM on February 5, 2013

Best answer: My stereotypical 90%+ OKC match is an artsy/geeky, vegetarian(ish) grad student who studied in Europe for a semester. In an alternate universe, I would be too, so it makes sense.

Quiet Storm.
posted by ryanshepard at 3:24 PM on February 5, 2013 [7 favorites]

Best answer: Hmmm... going on your OKC advice, if you buy into that...

In it's previous incarnation, Dozen Bake Shop. Very vegetarian friendly, good pastries and coffee, in Lawrenceville so you can stroll down a bit & window shop. Caveat: I haven't been there since they've changed hands.

I am incredibly interested in trying Waffallonia. Franktuary has veggie dogs. I can't imagine it would take a ton of time to either eat a waffle or a dog. There's also a crepes place in Shadyside.

You can go old school, to Klavon's Ice Cream parlor in the Strip. That place is a literal part of Pittsburgh history (the line from the St. Patty's Day flood is marked on the ceiling).

Or if you want to take a different twist, I'd say something like the Soup Tour on the South Side (this month?) or the Cookie Tour/Blossom Tour in Lawrenceville. It gets you out and walking, has a central activity, and if things don't go well you can always split up before the end.
posted by librarianamy at 3:30 PM on February 5, 2013 [3 favorites]

Best answer: Quiet Storm would be my first thought, too. Or Oh Yeah! - coffee, ice cream, and/or waffles in Shadyside.

Station St Hot Dogs always has interesting food stuff going on (and it's not all hot dogs - they seem to randomly do tacos, korean bbq, I don't even know what all). Their menu on the website doesn't have any of the newer stuff, but a recon mission ahead of time might discover if they have good veggie options.

In nicer weather, I'd say a trip up the Duquesne Incline for ice cream at the top. Maybe an idea to save for a future date!
posted by Stacey at 3:36 PM on February 5, 2013

Best answer: The Mattress Factory! Room-sized art installations. It is very, very fun.
posted by julthumbscrew at 3:47 PM on February 5, 2013 [3 favorites]

I'm not in Pittsburgh, but I just want to add that I am another person like phunniemee in that my okcupid first dates have all lasted somewhere between 6 hours to an entire day.

So don't make elaborate plans or anything, but the way I see it if I've chatted with the person a bit online, I have a good idea of whether or not hanging out with them for a few hours is going to be painfully awkward or not.

I would suggest something like coffee/drinks/brunch/etc. I've had a couple of really fun brunch dates where we wandered around after, went into shops, went to museums, whatever.
posted by fromageball at 4:15 PM on February 5, 2013

Best answer: Well, I'm not a graduate student that studied in Europe, but I am a single gal in Pittsburgh also doing the OKCupid thing (hi!).

Maybe it's just me, but I like first dates to involve booze. Not like crazy shot parties or anything, but just meeting at a bar for a few drinks and keeping it casual. That way, if things go well, we can continue having drinks, or go grab a late night bite or whatever. Plus, a cocktail or two makes me a lot more relaxed.

That being said, if you want a hipster but sorta pricey restaurant with a cool vibe, I really like Salt in Garfield. D's Six Pack and Dogs in Regent Square is popular and chill (though potentially not super veggie-friendly), and there's a few bars nearby should the evening go well.

I haven't lived here long enough to offer any more good suggestions, but I'll be taking notes from this thread for future reference. =)
posted by tryniti at 4:39 PM on February 5, 2013

Best answer: Waffallonia is one of the top reasons why I refuse to move out of Squirrel Hill. It's better for summer, though - you can grab your waffle + ice cream (go for the Speculoos ice cream) and then go to the church on the corner of Forbes and Murray.

There are Gallery Crawls downtown four times a year - there was just one a couple of weeks ago and the next is April 26th.

One of my best dates in Pittsburgh was going to La Gourmandine on a Saturday morning, getting a couple of pastries, and then eating them while we walked over to Jean-Marc Chatellier's French Bakery in Millvale.

The Carnegie Art Museum has a bunch of little events on weeknights - like this Thursday there's a guy coming to talk about Tiffany glass at the World's Fairs. This weekend they're hosting a cake competition. They're doing some pretty special stuff.
posted by punchtothehead at 4:47 PM on February 5, 2013 [3 favorites]

Best answer: I'd recommend The Church Brew Works — they have vegetarian food and tasty beer, and the building is pretty damn scenic.
posted by klangklangston at 4:59 PM on February 5, 2013 [2 favorites]

Best answer: The cafe at Phipps Conservatory. Beautiful scenery. A place to take a walk if things are going well. Great food with plenty of vegan options, and they serve alcohol and coffee.
posted by bfranklin at 5:37 PM on February 5, 2013 [1 favorite]

Best answer: I love Te Cafe in Squirrel Hill if you're looking for a coffee shop type date. Waffallonia, mentioned above, is awesome, but their seating might not be great for a first date.
posted by asphericalcow at 6:08 PM on February 5, 2013 [1 favorite]

Not a girl or in Pittsburgh, but I always make OKC first dates at a bar and this seems totally normal. If you don't have anything to talk about you can just have a drink or two and leave, there's no pressure and you're not locked into an all day/night thing and like someone else mentioned there's no awkward bill negotiation or having to get a check from someone.

Save the super awesome/fun/cute creative date ideas for the second date.
posted by bradbane at 8:26 PM on February 5, 2013

Best answer: It's not super quirky, but Over the Bar is a biker (as in cyclist) bar in the southside. And all of my vegetarianish grad-student friends are fans of it, as well. (If you ask me, I also think that a bike date is the greatest idea ever, so I'm biased.)
posted by vulgar_wheat at 10:12 PM on February 5, 2013 [1 favorite]

Just a word on *why* I (and a lot of people) prefer to schedule short/sweet OKCupid dates - I can't tell from an OKCupid interaction whether I'm going to like a guy enough to spend four hours with him (there are lots of people I love dearly IRL who would be totally unattractive to me online). Hence, I am much more likely to agree to a quick "let's see what we're like in person" coffee date.

However! If I like you in person, I might well be willing to spend another four hours with you. So plan for the best - don't have firm plans for right after the quickie date and and try to have the quickie date somewhere that allows for date extension. I also think it's a good idea to have a second-date suggestion ready going into the quickie date, to be deployed if things seem to be going well. Plan that three hour date! But be ready to bail or be bailed-upon after the meet-up part.
posted by mskyle at 5:59 AM on February 6, 2013

Best answer: Yeah, I met my wife on OKC in Pittsburgh, and she always made it a practice to have the very first date just be for coffee, for the above stated reasons.

Specifically, we went to Coffee Tree Roasters in Squirrel Hill.
posted by Chrysostom at 6:07 AM on February 6, 2013 [1 favorite]

Best answer: Guy in Pittsburgh here.

Bad venues:

-Coffee shops, especially the ones in Squirrel Hill/Shadyside. So many of them are filled with The Laptop Army and are deathly quiet. The only thing worse than an awkward first date conversation is an awkward first date conversation that EVERYONE can hear because no one else is talking. If you MUST do a coffee date, I'd suggest Barnes and Noble at the Waterfront - a little more traffic, movement, and noise, and you can go out to do other things if you hit it off over coffee.

-Sit down restaurants. This isn't a knock against any sit-down restaurant in particular, but it's too formal for a first date.

-Museums. It can be awkward to navigate the right ratio of looking/wandering/talking/joking. An exception might be a quirkier museum like the Warhol on the North Shore.



Good Venues:

-Mad Mex/BRGR/Spoon along North Highland are good, especially if you can grab two seats at the bar. Lots of noise and energy, no one really paying attention to your particular conversation.

-Pool at Dave and Buster's at the Waterfront. It's usually not crowded, pool is a low key activity. Lots of opportunities for flirting if the date goes well.

-Pub trivia nights. Hough's Tavern in Greenfield has one on Tuesday nights; there are others around the city. Trivia is great - it provides some conversational fodder as well as takes away the pressure to keep the conversation going constantly.

-Hikes/meetups. Venture Outdoors runs a lot of hikes, even this time of the year - being with other people can take some of the pressure off. Some of the hikes end in other activities (beer/wine tastings, soup, etc).

Message me if you need more ideas, and good luck!
posted by sherlockt at 9:45 PM on February 6, 2013 [1 favorite]