If You Want to Say: “I’m Sporty”
Make a Date For: Biking the Schuylkill River Trail. Set a slow pace so you can talk. (No need to prove you’re a Weekend Warrior just yet.)
If It’s Going Well: Pedal to the Conshohocken Brewing Co. (it’s past Manayunk if you’re coming from the city) and have suds and snacks—the bar is located along the banks and has plenty of bike parking. Conshohocken, 610-897-8962.
If You Want to Say: “I’m a Beer Lover”
Make a Date For:The Philly On Tap beer tour. Urban Adventures leads a small group through some of the city’s most popular and historic bars. Walk, learn just enough history, drink good beer.
If It’s Going Well: The tour ends in Rittenhouse, so head on over to the dark Good Dog Bar, grab a booth, and chat over another round and a great burger. Center City, 215-985-9600.
If You Want to Say: “I’m Crafty”
Make a Date For: Paint Nite Philadelphia. It sounds cheesy (okay, it is cheesy), but the combination of booze and an easy art project is the perfect ice-breaker. Held at bars around the city. Multiple locations.
If It’s Going Well: Tack on a classic cocktail from the moody, sexy Ranstead Room, where you can discuss the nudes that line the walls. (Arty … or not?) Center City, 215-563-3330.
If You Want to Say: “I’m Into Kitsch”
Make a Date For: Cherry Hill Skating Center. Roller skates. Black lights. Pop music. Arcade games. And the first Friday of every month is adults-only. Need we say more? Cherry Hill, 856-795-1919.
If It’s Going Well: Keep things classy at The Pub with “Texas Size” frozen drinks, cheap (but tasty) meats, help-yourself sides and endless kitsch. Pennsauken, 856-665-6440.
If You Want to Say: “I’m Outdoorsy”
Make a Date For: Forbidden Drive. Walk this easy, popular, hilly (the doable sort of hilly) path and appreciate urban nature. Park near Lincoln Drive to start your journey. Wissahickon Valley Park.
If It’s Going Well: After an hour, you’ll wind up at the quaint and historic Valley Green Inn, which has brunch, booze, hot chocolate and a waterfront view. Chestnut Hill, 215-247-1730.
If You Want to Say: “I’m Dark and Complex”
Make a Date For: Laurel Hill Cemetery. The monthly tours are intriguing and entertaining. (This month: “Victorians After Dark: Love and Lust in the 19th Century.”) North Philly, 215-228-8200.
If It’s Going Well: At Time restaurant, the mood is dark and sultry, live music is usually playing, and the absinthe is free-flowing. Midtown Village, 215-985-4800.
If You Want to Say: “I’m Urbane and Quirky”
Make a Date For: The Mütter Museum. This compendium of medical oddities can spark some pretty interesting discussions (and make you appreciate modern medicine). Center City, 215-560-8564.
If It’s Going Well: Museum-hop. Pay an extra $11 at the Mütter and get a ticket to the Penn Museum, too. After, grab an affogato (espresso poured over gelato) at Capogiro. Penn Museum, University City, 215-898-4000; Capogiro, multiple locations.