How they met: Olivia and Ryan met through mutual friends on a Halloween boat cruise on the Hudson River. Olivia was dressed as Cruella De Vil and Ryan was dressed as Superman.
How he asked: They were on vacation in California and on their drive from Napa to Monterey, they stopped at an overlook of the Golden Gate Bridge. Ryan set up his tripod to supposedly take a picture of them with the bridge in the distance but it ended up being a beautiful video of his proposal.
How they met: Naomey and George met at a Lebanese church festival. Naomey was talking to her cousin and George’s sister walked over to see Naomey’s cousin’s baby. George followed and ended up getting Naomey’s phone number that night.
How he asked: George had told Naomey the month he was going to propose because it coincided with Naomey moving back home after her final year of pharmacy school. It happened one night when George and Naomey were at a family gathering and he got down on one knee right in the living room, taking Naomey completely by surprise.
How they met: Jennifer and Brian met during their freshman year at Providence College. They both went over to a party with their friends and Brian challenged Jen to a game of beer pong. They agreed that the loser had to buy the winner a drink at the bar later that night. To this day, Brian says he lost the game on purpose, so that he had an excuse to hang out with Jen again. After Brian bought Jen her winning drink, the two were inseparable.
How he asked: Brian took Jen to the Brooklyn Bridge, one of their first date spots and a place they love to visit every year. They walked across the bridge and down to the water with the city skyline in the background and Brian popped the question as a photographer documented the entire proposal. They then celebrated their engagement with a two week California road trip down Route 1!
How they met: Kenesha was a bridesmaid in her best friend Kelly’s wedding; Frank was a groomsman and cousin of the groom. They first met at the rehearsal dinner but it was at the reception where they really connected. They could not get off the dance floor.
The proposal: They went out for a date night at one of their favorite restaurants on Staten Island. Kenesha remembers getting home and noticing that the lights in their house were on. She walked inside and the house was filled with red roses and handwritten love notes. She followed the trail of roses and at the end was the ring in its box. As she turned around, she found Frank down on one knee asking her to marry him.
How they met: It started with two right swipes, Dan’s cute dog, and Ally’s bright smile. They had over twenty mutual friends, grew up in neighboring towns, and had taken the same train for eight months commuting into the city. They had even been at the same parties before without meeting. They now like to tell all the Tinder couples out there that there’s hope!
The proposal: Dan planned a romantic vacation in California for the two of them visiting Monterrey, Big Sur, and Napa Valley. Eager to relieve the stress of having the ring in his possession, Dan decided he was going to ask the big question the second day of the trip as they planned to drive along the coast down Highway 1. After a full day of driving, stopping and hiking, Dan pulled off the road to an empty lookout spot. After Ally made him pose for a few pictures, he got down on one knee, apologized for it being an odd-numbered day, and asked her to spend the rest of her life with him.”
How they met: Devin and Bobby met on Match.com. They were both on Match for about two weeks before they first connected. They chatted for a few days before the conversation went dead, leading Bobby to think Devin wasn’t interested in him. Luckily, Devin reached out again a few days later and their first date shortly followed.
How he asked: Devin and Bobby planned a trip to Greece and Bobby thought it would be the perfect place to propose. Once they were in Santorini and in front of the caldera overlooking the ocean, Bobby knew it was the ideal spot. He asked an American tourist to take a picture of them and Bobby popped the question in front of the most stunning ocean views.