Date night for parents is a time to step away from the to-do list and have fun. However, not all families have a trusted village to call on to watch the kids for the night. Sure, we take the kids to family-friendly restaurants or attractions, but let’s face it — not all adults find these places enjoyable or chill.
Adults with children must rethink date nights — it won’t always be getting dressed up, eating overpriced tapas, and hours of deep conversation. Sometimes, it will look like jeans and sneakers, your child in tow, ordering off the kid’s menu. And that is OK.
There are places in Pittsburgh where you can take your kids on a date night and still feel like grown-ups stepping away from the daily grind. Pittsburgh City Paper compiled a list of places you can go with or without the kids, where weary parents will find free babysitting, kid-friendly deals, and more.
Pins Mechanical at SouthSide Works
407 Cinema Dr., South Side. pinsbar.com/locations/pittsburgh/events
Despite being described as an “adult playground,” Pins promises fun for the whole family while unlocking nostalgia for when you didn’t know how to change a diaper. Before 9 p.m., the SouthSide Works bar and entertainment venue provides a safe space for all ages to be playful, inviting the entire family to unwind with friendly competition over foosball, pinball, or giant Jenga.
The kids can wander around the free-play arcade while you and your partner lovingly talk trash during a game of ping-pong. There is also bocce, table soccer, and a two-story slide big enough for adults. Every Sunday, kids enjoy a complimentary soda and free duckpin bowling.
While the weather is nice, you can enjoy the outdoor seating and life-size patio pong. You can even bring the furbaby because Pins loves dogs.
Pins focuses more on beer and cocktails than food, but SouthSide Works has several family-friendly dinner options within walking distance. You may even find a food truck or two parked outside some nights.

Pittsburgh Public Theater at the O’Reilly Theater
621 Penn Ave., Downtown. ppt.org
Pittsburgh Public Theater (PPT) offers diverse and entertaining plays season after season. Some of these shows are family-friendly, but getting most children to sit quietly through two hours of anything can be challenging.
Thankfully, PPT’s Sitter Sundays has entered the chat. During select Sunday matinees, PPT offers childcare for all ages led by Jovie of Pittsburgh, described in a news release as a “trusted care resource for the Pittsburgh region.” Enjoy the show while the little ones experience themed workshops in the O’Reilly rehearsal hall.
“We wanted to open up opportunities for families to come to the theater and not have to worry about childcare,” Dominique Briggs, PPT’s senior manager of Public Works and Partnerships, tells City Paper. “We chose Jovie because they are a reputable, trustworthy service that cares for children — they are experienced in event childcare, and we wanted nothing but the best for our patrons.”
Sunday Sitters is available during several shows for PPT’s 2024-25 season, including the adaptation of J.R.R. Tolkien’s The Hobbit, the holiday hit A Christmas Story: The Play, the Pittsburgh premiere of Trouble in Mind, and Edward Albee’s intense drama Who’s Afraid of Virginia Woolf?
Childcare can be reserved during checkout or as an add-on to previous ticket purchases. There are limited spots for each show, so plan ahead.

Pittsburgh Opera at the Benedum Center
Seventh St. and Penn Ave., Downtown. pittsburghopera.org
Pittsburgh Opera has launched free childcare during the Sunday matinee performances of its latest productions, Tosca, Cavalleria Rusticana, and Pagliacci, at the Benedum Center. Let the bel canto wash over you with no worries as the kids are cared for by trained, certified professionals in the Benedum’s multipurpose room.
The Pittsburgh Opera website states that the organization “worked closely with their partners at the Pittsburgh Cultural Trust, which owns and operates the Benedum Center, and Priya Amin, the founder of on-site childcare provider Flexable, to bring this program to life.”
“For families with young children, finding and paying for a reliable babysitter can be a real barrier to attending arts and entertainment events,” Chris Cox, Pittsburgh Opera’s director of marketing and communications, said in a press release.
Space is limited, so pre-registration is required for children ages 2-12. Children 6-12 are welcome to sit in the audience at a discounted ticket rate.
“We hope to offer this again at future performances later this year, and that our childcare program inspires copy-cat offerings from other arts organizations once they see how successful it can be,” said Cox.
Museum of Illusions on the North Shore
267 North Shore Dr., North Shore. moipittsburgh.com
The Museum of Illusions encourages the family to think outside the box, inside the box, and on top of it. Kids like to touch everything, so let them explore this museum, where touching the exhibits is accepted and encouraged.
The museum is self-led, so how long you engage with the interactive wonderment is up to you. Take your time — you may get lost in one of the mind-twisting installations. This can also be an excellent time to capture the family photo for this year’s holiday card, as the perspective-changing illusion rooms make for artful photo ops.
This article appears in Oct 9-15, 2024.





