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Kaylin & Sydney – A Surprise Rooftop Proposal

Kaylin & Sydney – A Surprise Rooftop Proposal

Nicole Kiesling photography USA Lesbian gay same-sex queer surprise proposal engagement Dancing With Her online wedding directory magazine

Kaylin and Sydney first “met” when Kaylin was the teaching assistant for the statistics course that Sydney had been putting off for years to pursue her degree at The University of Iowa. Although they never really interacted throughout the semester (Sydney hates speaking in class), Sydney started crushing on Kaylin hard, from afar, of course.

In the past, Sydney has always been pursued rather than the pursuer. So naturally, she did nothing about this crush except interrogate her bar patrons for any information she could get on Kaylin’s social and dating history. Meanwhile, Kaylin only knew Sydney as the student with the best handwriting in the class. That would sometimes crack jokes in her homework (Kaylin likes to think that these were subtle flirting attempts).

Months passed with no real developments between the two. Except for an Instagram follow request from Sydney that Kaylin reluctantly accepted given the dynamic of their former teacher/student relationship. Mind you, they are only a year apart in age. It wasn’t until Valentine’s Day in 2019 at a planned parenthood fundraiser that their paths finally crossed for real. Ironically, the fundraiser was held in a bar that both Kaylin and Sydney despised and would not usually go to. But HELLO, a planned parenthood fundraiser on V-Day? Come on!

Sydney arrived with her coworkers after she got off and spotted Kaylin at the bar with her friends. Kaylin was wearing a blazer/bow tie combo that gave Sydney heart palpitations. After months of hearing about this girl, Sydney’s friends encouraged her to “go say hi.” To which Sydney replied, “ARE YOU CRAZY?! I can’t do that!”.

This nervous/excited back-and-forth between Sydney and her friends took place for nearly twenty minutes. Then suddenly, Kaylin was nowhere to be found, and Sydney panicked. She went looking on the back patio and spotted her. Keep in mind, this is February in Iowa, and it was below freezing outside. So Kaylin was one of the only people on the patio.
Sydney pretended to be looking for a friend and even walked as far as the back alley to avoid being obvious. Finally, Kaylin noticed Sydney walking back inside and casually said, “what’s up?”

From that moment, the two were inseparable. They stayed up that whole night just chatting at Kaylin’s apartment, and a month later, they were officially dating. Fast forward two years and two dogs. A master’s degree, a house together, job changes, and a pandemic later, Kaylin knew the proposal had to be just as epic as the origin story. She enlisted the help of one of her childhood best friends-now, wedding-photographer, Nicole, and spun a tale to Sydney about Nicole needing more queer couples in her portfolio. Just like that, the photoshoot was booked, and Sydney hadn’t sniffed it out.

Kaylin and Sydney were traveling to Kaylin’s hometown of Jacksonville, Florida, and were scheduled to do the photoshoot the first day they were there. Usually, Sydney is quick to figure out when something “was up,” but for the first time, she was genuinely surprised.

Atop a rooftop, with a view of Kaylin’s college apartment building and the Jacksonville skyline, Kaylin popped the question. After lots of screaming, happy tears, and kisses, Kaylin led Sydney to a small speakeasy-style bar where Sydney was surprised AGAIN by her sister and brother-in-law. Who had flown in, as well as Kaylin’s friends and family.

Cheers to the best beginning of the new year and a new life together!


Photography by Nicole Kiesling

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