Tag Archives: Mr. Smalls

Whether your first date or fiftieth date, Pittsburgh has it all to make it a good one.

14 May

So I’ve been thinking…I feel like people don’t make enough of the scene in Pittsburgh. This is one amazing city for romance. Whether just starting out on your first date or going out after 50 years of marriage, here are some options, bound to get you at least a kiss…

  1. “Here we go Steelers, here we go…”  Who doesn’t like seeing people beaten up while a billion people cheer them on? Now, when I came to this country (I sound like an 80 year old immigrant, but I’m not) I had no real love of football.  The first time I went to a pro football game was in Heinz Stadium (in October) and I was totally floored. It was AMAZING! The energy level of the entire thing, from tailgating to the actual game, is enough to leave you and your date smiling. Honest to goodness.  If you can’t afford tickets to a game, tailgate and then head to a bar to watch the game.
  2. Take a trip up the Duquesne incline and have drinks (or dinner) on Mt. Washington.  The restaurant we frequent is called The Grandview Salon and although we’ve never eaten there, the view from the bar alone is worth the trip up.
  3. Dine at a train station gone restaurant…the Grand Concourse.  To start, seat yourselves at the bar and start with oysters (market price) and listen to the pianoman play.   When dinner rolls around, the main room is almost overwhelming how stunning it is, but there’s a room at the back, with a river view perfect for a late night dinner.  The city lights up in front of you and it seems all the guests eating are really happy to be there.  The restaurant is hailed for its amazing seafood (the sea bass is to DIE for), but there’s also turf options if you’d like. Then take a stroll along the river, maybe popping into another bar for a final drink.
  4. For something a wee bit more intimate, Dish Osteria Bar is ALWAYS a win. The venue itself is smaller.  The tables themselves are smaller than the usual, so there’s plenty of opportunity for ‘mistaken’ footsies, hand brushing and sharing.  The staff are great and the owner (the last few times I’ve been) is usually around…which means it’s a place that takes pride in its service.
  5. Go to the theatre…there are so many live show options, I don’t really know which to recommend…just don’t take your date to see Shakespeare if they didn’t like it in high school…chances are, their taste in olde Englishe probably hasn’t changed.
  6. If live theatre isn’t your thing, how about a concert at Mr. Smalls? Before, or after, pending on the weather and whether it’s open or not, head three blocks over to the skate park to watch some talented (and not so talented) people skate. Nothing is as bond building as watching others get battered and bruised (see date option number 1).
  7. Take a Saturday morning stroll and picnic.  Head down to the historic strip district to pick out your lunch fare and then drive into Schenley Park to picnic it out. Don’t forget a blanket, and even if it rains there’s a big white tent.
  8. Let your wild side show…go to the zoo! Who doesn’t get happy seeing cute animals?? Plus you can have stories like, “our first kiss was in front of a bunch of wild monkeys”…how awesome is that?
  9. Little E’s has live jazz…I’d suggest though, you hit up dinner somewhere and then get there just as it starts (each show has its own start time, but 8:30 seems to be a safe bet) check out their website for daily event details before you go…
  10. For something a bit different, head to Gypsy Café in the south side on a Thursday night. They have a seasonal menu and live gypsy music (played by Gypsy Strings) starting at 8:30 pm. I’d reserve a table for 8 pm so you can get some talk time in with your date before the band starts up.  Desserts are made in house and, like Dish, the owners are usually there to greet you.  If you’re feeling spiritually adventurous, go on a Friday for tarot readings…

There are so many more options, and once I explore a bit more, I’ll post them.  Happy dating Pittsburgh!