From high school prom-goers to wedding parties, just about every couple has made a stop on Grandview Avenue in Mount Washington to snap a photo of themselves in front of Pittsburgh’s city skyline. And why not? Up on Mount Wash, you get an unobstructed — and romantic — view of Pittsburgh’s three rivers and the impressive steel buildings and bridges that first put this city on the map. To top it all off, nothing could be quainter than riding up ol’ Coal Hill on Pittsburgh’s last remaining vehicular incline planes—the Duquesne or the Monongahela.
We Pittsburghers are obsessed with our three rivers and 446 bridges and relish any opportunity to revere them. That’s why, every now and again, we spring for a romantic evening of dining, drinking, and dancing aboard the Gateway Clipper. Whether it be a sunset cocktail cruise or special holiday event, setting sail on the Gateway Clipper guarantees you and your date will get cozy together to take selfies with the dazzling city skyline as the backdrop.
No, this date doesn’t entail a late night out at seedy strip club. In fact, just the opposite: it involves an early morning of breakfasting on diner food at Pamela’s or DeLuca’s before shopping at crowded local produce stands, ethnic grocers, and sidewalk vendors. While you have to forfeit some extra ZZZs for this date, it’s always worth it: not even Giant Eagle Market District can provide this selection of culturally-diverse goods — Italian, Mexican, Asian, Peruvian, Polish, etc. — at such low prices.
While outsiders may know Pittsburgh for its sports culture, the city also boasts a thriving arts community. What’s even better is that much of our art can be enjoyed for free during Unblurred: First Fridays on Penn (held monthly) and the Cultural Trust’s seasonal Gallery Crawls. You and your date can do some serious art analysis (or not) while enjoying a courtesy glass of wine at each venue.
Some may see drive-in theaters as an artifact from a bygone era, but Pittsburghers still understand their true value. After all, why would you spend $10 on a single movie ticket when you could pay $6.50 for a double feature? Plus, being in the comfort and privacy of your own car means you can talk, cuddle, and, uh, smooch with your date as much as you’d like. Whether you prefer the Twin Hi-Way Drive-In in Robinson Township or the Dependable Drive-In in Moon Township, these “passion pits” (as they were once labeled) make for a great summer date night.
Pittsburghers love hanging out in churches, especially those that house our favorite spirits (and beers and wines, too). The Church Brew Works — where the former altar area is now used to brew craft beer in giant steel and copper tanks — is a sure conversation starter on a first date. The Altar Bar in the Strip, Charlie Murdoch’s in the South Side, and Mr. Small’s Fun House in Millville are all former churches-turned-entertainment venues that make for an enjoyable date night out. And Pitt students looking for a super chill way to get to know a cute classmate better can head to The Sphinx Café in Oakland to smoke hookah and eat traditional Arabic food.
Pittsburgh’s Cultural District boasts some first-rate venues, from the regal Heinz Hall, Byham Theater, and Benedum Center to the contemporary O’Reilly Theater and August Wilson Center. For a small city, Pittsburgh has an impressive performance schedule jammed packed with musicals, plays, concerts, comedy groups, dance troupes, and operas. With several new, hip restaurants opening in the Downtown area, we have plenty of options when it comes to planning “dinner and a show.”
A night in the South Side usually starts with good intentions but ends a little sloppy, mostly because the neighborhood has the greatest concentration of bars per block in the entire city. That means you can stumble from speakeasy to saloon to nightclub to dive bar in one evening without ever interrupting your buzz. After it’s all said and done, you and your lover can curb your hangover by devouring some late-night fare. Or, you could just head back to Jack’s Bar bright and early to start drinking again: it opens at 7 am sharp every day but Sunday. 