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8 Top-Rated Date Spots for Professional Pittsburgh Singles

July 28, 2021

Summer dating in Pittsburgh is a double treat! You can get to know someone new, and enjoy the outdoors at the same time. You’ll want to take your date to a location that promotes conversation and involves a shared interest. There are endless possibilities in the Pittsburgh area that range from beautiful outdoor dining to exciting summer events. Take a look at this list of the 9 best places to dine, play, and explore while dating in Pittsburgh

8 Incredible Date Places To Enjoy

Bridges and Bourbon

a fancy cocktail with smoke
Image courtesy of Bridges and Bourbon

Bridges and Bourbon is the perfect place to take your date out for a cocktail. The restaurant focuses on contemporary drinks that are not only visually appealing but also delicious. They have an appetizer menu and an extensive drink list that includes bourbon, whiskey, cocktails, international drinks, mocktails, and more. Meet your date for happy hour to enjoy cocktails and charcuterie. Dating in Pittsburgh does not always have to include a full course meal — Bridges and Bourbon proves that even a happy hour can be classy and enjoyable for both you and your date.


a plate of food
Image courtesy of Altius

If you are searching for a contemporary, romantic restaurant, Altius is an incredible place to take your date. Altius is a fine dining experience, and the restaurant has been recognized locally, nationally, and abroad for its excellent food and drinks. The executive chef’s approach to the cuisine is contemporary America that is refined and modernized. Not only is the food delicious, but you will also have a stunning view of the city from Mount Washington. 

Pittsburgh Winery Tasting Room

bottles of wine in a row
Image courtesy of Pittsburgh Winery

The Pittsburgh Winery produces bold dry wines in Pennsylvania with world-class grapes grown in California. It is a boutique-urban winery that doubles as a venue to unwind and listen to relaxing music. Although you may not expect much from a winery that is not in wine country, they will exceed your expectations. The Pittsburgh Winery’s tasting room offers a comforting atmosphere with perfectly paired wine and cheese platters. 

Pittsburgh International Jazz Festival

a saxaphone on sheet music
Image courtesy of Visit Pittsburgh

Take your date to the Pittsburgh International Jazz Festival to enjoy the music of talented artists in the city. This year’s event has been moved to the Highmark Stadium in Station Square to ensure there are COVID-19 precautions to make sure that all attendees are safe. The ticketed event will be September 17-19, 2021, and features jazz icons, some of the most exciting in the scene right now, such as Marcus Miller, Dianne Reeves, Gregory Porter, Jazzmeia Horn, and many more. 

Phipps Conservatory

a room full of tullips
Image courtesy of Phipps Conservatory and Botanical Gardens

The Phipps Conservatory and Botanical Gardens is a beautiful iconic date spot. The conservatory is a serene oasis in the middle of Oakland and encompasses 15 acres. There are 14-room glasshouses and 23 distinct gardens that are great for photo opportunities with your date. It is also a relaxing place to chat and get to know each other better without the background noise of a bar or restaurant. 

Andy Warhol Museum

inside the Andy Warhol Museum
Image courtesy of the Andy Warhol Museum

Since Andy Warhol was born in Pittsburgh, the Andy Warhol Museum holds the most extensive collection of Warhol’s artwork and archived materials. The artwork serves as great conversation starters for you and your date. In addition, it can be interesting to compare how both of you interpret the art that icon Andy Warhol put together. 

Pittsburgh Restaurant Week

a plate of pasta
Image courtesy of Pittsburgh Restaurant Week

Pittsburgh Restaurant Week is the most delicious time of the year and the perfect way to help local businesses in the post-pandemic world. The event’s mission is to highlight wide-ranging dining experiences in the Pittsburgh area while also offering delicious meals at exclusive prices. From August 9-22, you can choose from various participating restaurants to take your date out to — from BYOB spots to fine dining restaurants. 

Hartwood Acres Park Summer Concert Series

Summer Concert Series lineups
Image courtesy of RAD Works Here

The Hartwood Acres Park Summer Concert Series is the perfect way to enjoy the summer weather and spend time with your date. Throughout the summer, Allegheny County Parks will offer free concerts every Sunday at the Hartwood Acres Park. There are also summer concerts every Friday at the South Park Amphitheater. Enjoy the music and grab a bite to eat at the food trucks for an amazing summer date. 

Dating in Pittsburgh can be fun, with endless date venues this summer The Modern Matchmaker is a boutique matchmaking service for upscale singles looking for a committed relationship. Contact us to get started so that you can take advantage of these date night ideas this summer that’ll be sure to impress your date!

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