A Heartwarming Rooftop Proposal in Old City
“Philadelphia is a place that has allowed us to love openly and proudly.”
Kelly Hollis (left) and Allie Millevoi at their Old City engagement / Photography by Jennifer Syl Photography
Proposal season is here, and we’re kicking things off with a touching rooftop “will you” in Old City, which took place shortly before Thanksgiving. It’s filled with surprises (of course), but is most importantly a powerful tale of love. Photographer Jennifer Gordon of Jennifer Syl Photography captured each moment so beautifully, which you can see below. And if you have a proposal story you’d like to share, do so here!
The couple: Allie Millevoi, 28, and Kelly Hollis, 25, both of Old City
How they met: The duo connected on TikTok when Allie, who was living in Philly, posted a video — what she says may have been a “thirst trap” — and Kelly, who was based in Los Angeles at the time, commented. “She won me over with her comment, which was ‘woah,’” says Allie. The two exchanged DMs, began texting, and hit it off. They made long distance work for more than a year, then Kelly moved to join Allie in Philly.
The proposal plan: Allie and Kelly dated for two and a half years before getting engaged — though Allie says she would’ve proposed within the first month. “When you know, you know,” says Allie. She also says she knew she’d be the one to pop the question. She wrangled their family in Florida, North Carolina, Ohio, and Pennsylvania to be there for the big moment, found their photographer in the Philaqueens Facebook group, and tapped their friend Lily for the proposal spot — the rooftop of her home in Old City. The decoy: a wine night at Lily’s, naturally.
The pre-question nerves: Allie was “shaking like a leaf” in the days ahead, because she knew Kelly had no idea. “Her nails weren’t even done — oops,” says Allie.
Kelly’s reaction: She was “floored,” cried, and made a lot of “Are you kidding me” exclamations. “I felt like I was on cloud nine and, just a couple weeks later, still feel the same,” she says.
Allie’s reaction: Relief, excitement, and gratitude — particularly for their photographer, who stood in the cold for more than an hour to “capture the most beautiful pictures we could’ve asked for,” she says. “She helped me with every aspect of the proposal and kept me calm as I was about to experience one of the most exciting moments of my life.”
The post-proposal plot: Allie had more up her sleeve. She surprised Kelly again by gathering their friends and family at The Plough and the Stars to raise a toast. “We ate and drank and celebrated this milestone with our favorite people, in our favorite bar,” says Allie.
The wedding plans: Nothing yet, as they want to enjoy the holidays as future to-be-weds before planning begins.
A word on their love story: “As a couple in the LGBT+ community, we feel so incredibly blessed and lucky to have the support of our family and friends and everyone in between,” says Allie. “Philadelphia is a place that has allowed us to love openly and proudly.”
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