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Christmas season really is the time for engagements.

Just ask famed Philly jeweler Steven Singer, who says Christmas is easily his busiest time of the year selling engagement rings. New Year’s Eve ranks right behind it. And over on the 1700-block of Addison Street in Rittenhouse, neighbors keep champagne ready for when people get engaged in front of the iconic lights.

If you’re planning to get engaged this season, you need a ring — if that’s your thing. But you also need a plan. Here’s where a few experts say you should pop the question in Philadelphia.

Steven Singer, jeweler

Singer is a fan of the classic tourist spots: The Rocky Steps, Independence Hall, the Liberty Bell, the top of City Hall and the Philadelphia Zoo. He said you can also never go wrong with the first restaurant you took your significant other.

Maybe once or twice a month, Singer witnesses engagements at his own store on Jewelers Row.

“We recently had someone make a sign put it in the window, put the actual ring in the box in the window and pretend like they were window shopping,” he said. “She looked in the window and came in and got it. We had a little love seat set up.”

Hughe Dillon, photographer/Philly Chit Chat proprietor

“I think the best place to propose is at the Waterworks, on the pier that overlooks the waterfall,” Dillon said. “There’s a beautiful view of Boat House Row as it glows in glorious holiday colors, and then behind you is one of the most spectacular views of the Philly skyline and the Art Museum. It’s very romantic, and very Philly. Plus in a decade when you bike by the spot with your kids, you can point out the spot to them.

“Too cliche would be Rittenhouse Square, but it really is magical with all the trees beautifully lit, as the hustle and bustle of people make their way through the park. It’s cliche, but memorable Philadelphia.”

Cara Schneider, media relations director Visit Philly

Schneider has almost the same recommendation as Dillon. But rather than pick the pier, she recommends climbing above to the light gazebo overlooking Waterworks, the Schuylkill and Boathouse Row.

“It is 100 percent successful,” she said. “That’s where my husband proposed in late December [last year].”

Schneider also recommended the LOVE or AMOR statues, the Pennsylvania Academy of Fine Arts, favorite restaurants and the City Hall observation deck. These are some of her more off-beat picks:

Tribute to Abruzzo, Italy mural: It’s an Italian wedding countryside scene on Le Virtu on East Passyunk Avenue.


Sixth and Chestnut: Schneider recommends this place for gay couples. The intersection features a historical marker and is where many of the earliest LGBT protests occurred in the city. “That’s a cool location for how far we’ve come,” Schneider said.

Saint Stephen’s Church at 10th and Ludlow: “On this spot Ben Franklin did his famous kite experiment,” Schneider said. “If you want to rekindle or recapture the electricity there’s that spot.”

The Whispering Benches at Memorial Hall: Over in Fairmount Park, you can sit on one side of a bench and whisper to your significant other on the other side.

Bonus: Holiday photo ops

If you want your engagement photos to be filled with holiday spirit, stop by any one of the city’s top destinations. Time your shot perfectly at the Macy’s light show or the new City Hall light show. Have someone at the ready on one of the ice rinks, or center yourselves around any of the neighborhood Christmas trees.

Mark Dent is a reporter/curator at BillyPenn. He previously worked for the Pittsburgh Post-Gazette, where he covered the Jerry Sandusky scandal, Penn State football and the Penn State administration. His...