Struggling to think of something fun to do this Valentine’s Day? Tired of looking for an open restaurant reservation? Skip the hassle and spend this Hallmark card holiday skating, petting cute cats, taking in the city’s natural beauty, or playing a few games, all without breaking the bank.
Fish for fun at Kura Sushi and Pins Mechanical
The SouthSide Works has come a long way from its days as the place where you go to raid the clearance section at Urban Outfitters. Visitors to the complex will find a diverse array of new food and entertainment concepts, and events ranging from outdoor pro wrestling to beer festivals.
The author discovered firsthand that it also makes an attractive, affordable dating destination. Stop by Kura Sushi (415 Cinema Dr., South Side. kurasushi.com) for plates of raw fish, beef, and other entrees — most priced under $5 — delivered right to your booth by a constantly moving conveyor belt. Kura also has a Valentine’s Day chirashi bowl special that comes with a heart-shaped sauce dish.
Afterward, take a few steps to the nearby Pins Mechanical (407 Cinema Dr., South Side. pinsbar.com), where duckpin bowling, pinball, and other retro delights await. Even better, the console arcade games are free to play, meaning you can develop some romance over rounds of Pac-Man or BurgerTime.

Walk the Allegheny RiverTrail Park and into the Market District Giant Eagle bar
Aspinwall is a study of opposites. The borough offers the abundant, sprawling, suburban-like retail of the Waterworks, yet also boasts plenty of natural beauty, including several surrounding trails. Sure, there’s the kind of ample parking you’d expect at a strip mall, but bus commuters will also find surprisingly decent access via the 75, 91, and other routes.
Regardless of how they end up there, couples can check out the Allegheny RiverTrail Park, taking in scenic views of boats, marine life, and other Allegheny River sights.
From there, head to the Waterworks Market District Giant Eagle bar (910 Freeport Rd., Aspinwall. marketdistrict.com/stores/72), a hidden gem often occupied by WFH laptop jockeys and shoppers looking for a break. (A friend once called the bar the best casual date for parents due to the availability of temporary childcare at the in-store Eagle’s Nest). What the space lacks in hipness it makes up for in cheap craft beer and wine pours.
Plus, if you’re hungry, the adjacent market provides prepared foods, all of which will be far less expensive than a typical dining experience at a restaurant crammed with V-Day diners — that being said, make sure to generously tip whatever Market District employees are assigned to bartend that day.
Thrift, eat, and drink in Garfield
Garfield has a decidedly punk vibe that prioritizes affordability, accessibility, and inclusivity. The classic date trifecta would be to search for second-hand goods and records at Fifty One Ten Vintage (110 Penn Ave., Garfield. fiftyonetenvintage.com), then cross the street for pizza and beer, respectively, at Spak Brothers (5107 Penn Ave., Garfield. spakbrothers.com) and Two Frays Brewery (5113 Penn Ave., Garfield. twofraysbrewery).
There are more options than that, however, all within a short walk on Penn Ave. Meet furry friends at Black Cat Cafe, check out the goods at East End Community Thrift, support local artists with a small gift purchase at Workshop PGH, or challenge your honey to a boardgame while sipping cups of Lapsang Souchong at Bantha Tea Bar.
Don’t be a jagoff at Frick Park and Evergreen Cafe
Evergreen Cafe (7330 Penn Ave., Point Breeze) has earned the reputation as being home to the 2023 winner of Pittsburgh City Paper’s Best Jagoff award, aka the occupier of the city’s most infamous parking spot. Beyond that, though, those looking for a proper dive bar with affordable menu options could do worse, especially after working up an appetite walking around Frick Park.
Depending on how far you and your date are willing to go, the section of Frick Park located closest to Penn Ave. (where Evergreen is located) has well-maintained, walkable trails perfect for a quick, scenic stroll. If the weather seems less than favorable, opt for The Frick Pittsburgh — conveniently located at the park’s edge on Reynolds St. — where it’s free to enter the gardens, the Frick Art Museum permanent collections, and a section of the Car and Carriage Museum.
After a Frick-filled time, head to Evergreen (about a 10-minute walk from The Frick Pittsburgh) for draft beer, unpretentious Mexican food, and a laid-back atmosphere, all curated by the most hated person in all of Pittsburgh. If your date is unfamiliar with this bit of lore, it makes for a colorful conversation topic sure to get the night off to a good start.
Boogie into Neville Roller Drome and Carmody’s Grille
Rom-coms often portray rollerskating as the ultimate aphrodisiac, and the pastime became more popular among adults over the pandemic, both as a way to stay active and to capture some joy in a bleak time. Strap on some quad skates and head to Neville Roller Drome (5109 Neville Rd., Neville Island. nevillerollerdrome.com) where, for a small fee, couples can take a few spins around the floor, all while a DJ spins everything from “contemporary hits to old school tunes,” according to the facility’s website.
A short walk from the Drome brings you to Carmody’s Grille (4905 Grand Ave., Neville Island. carmodysgrille.com), a cozy restaurant/bar located in a historic hotel. Pittsburgh City Paper News Editor Colin Williams personally suggested this location for its above-average pub grub, decent beer selection, and friendly staff. Overall, you and your date are sure to find something to sate a post-skating appetite.
This article appears in Feb 7-13, 2024.







