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Perfect Proposals that Flashed Back to First Dates

Return to your roots before your relationship blooms into a beautiful marriage.

photo by TimeSmart Images


At the core of every romantic relationship is the first date. Back before the joint bank account, sharing a bathroom, meeting each other’s families and falling in love, every couple had that first — most likely nerve-wracking and potentially awkward — date.

These first dates often signify the beginning of something wonderful for couples, which is why people often return to — or reminisce on — the location of their first date.

These couples are prime examples of how a blast from the past can make a proposal that much more special.

Gabriella DaPra & Leo Gigliotti

Photos by Araujo Photography

After having breakfast in the Strip District and spending the morning strolling around Pittsburgh, Leo Gigliotti asked Gabriella DaPra a very important question: Will you check out this pavilion with me?

Leo told Gabriella that his friend wanted to rent a pavilion in a park for a summer party, and he needed there to be a playground nearby. The only place that fit the criteria was the South Park Fairgrounds.

The Fairgrounds — particularly the Oval and clock building — held significant importance to Gabriella, as that was the place of the couple’s first date.

When they arrived at the Fairgrounds, Leo asked Gabriella to get out of the car so that he could take a picture. Though annoyed she had become an active participant in the seemingly random errand, she finally complied, and the couple began to walk to the park.


Leo mentioned that this was the place of their first date and first kiss three years prior. Gabriella responded, saying that she thinks about their first date every time she passes the clock building.

“How crazy would it be if we kissed here, three years later, as fiances?” Leo asked.

Out of surprise, Gabriella physically jumped away from him as he got down on one knee. He encouraged her to move closer, as they had hidden friends recording the moment.

After reciting a loving speech, Leo asked Gabriella to marry him. The surprises continued when he brought her to an engagement party he had planned for her.


Gabrielle Spina & Joseph Monaco

Photo by TimeSmart Images

Garbrielle Spina had a very clear vision of how she wanted her boyfriend of five years to propose. Gabrielle told Joseph Monaco that when he finally popped the question, he should make sure her nails, makeup and hair were done and that he have a photographer hidden somewhere.

Joseph did not heed her advice.

The couple’s five-year anniversary fell on a Sunday. Though Gabrielle is the first of the pair to be up and moving, on this day, Joseph sprang out of bed before her and retrieved their memory box. He presented the box, filled with ticket stubs from sporting events and movies, to an annoyed, confused and not-yet-awake Gabrielle.

“He’s not super sentimental, and it’s not something he would usually do,” Gabrielle says.


However, as they went through the box, memories began to come back, and the couple ended up laughing and reminiscing until Gabrielle came across a silk bag. She assumed the bag, which clearly had a box in it, was a watch she had bought Joseph that he never wore.

Upon opening the box, Gabrielle discovered an engagement ring, along with the movie ticket from their first date — The Lion King 3D.

“It was not what I thought it would be at all,” Gabrielle says. “But it was perfect.”

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