This Massachusetts couple jumped out of a plane — then got engaged
Alissa Litchfield sprung 8,000 feet to find Ryan Richards on bended knee.
As Pembroke’s Alissa Litchfield, 24, prepared to jump out of a plane for the first time earlier this month, her instructor turned to her and chose his words carefully.
“I said, ‘Are you ready to take the plunge?'” recounted Alex MacKenzie, general manager and instructor at Go Skydive Boston in Hanson.
MacKenzie knew something that Litchfield did not. Litchfield’s boyfriend, Ryan Richards, who had already dived from the plane, was falling through the sky on a mission. Richards intended to propose as soon as Litchfield’s feet touched the ground.
“Everyone was in on it except her,” MacKenzie said.
Litchfield, a preschool teacher, and Richards, 29, an orthodontic assistant, both grew up in Pembroke and shared mutual friends, but didn’t meet until four years ago at Quincy’s now-closed Iron Furnace restaurant and bar. The duo loves adrenaline-filled adventures. Their first date was at Water Country in Portsmouth, New Hampshire, and they’ve gone zip lining and cliff jumping together in the Dominican Republic. So it only made sense for Richards’ proposal to involve something daring.
However, Richards’ plan for a sky diving proposal was thwarted last summer when Litchfield became pregnant with their daughter, Mila Rae, who was born June 2. Richards thought about proposing in other ways over the past year as the couple excitedly prepared for the birth of their daughter, but decided he’d stick to his original plan once their child was born. After asking Litchfield’s parents to babysit, he surprised Litchfield on the morning of July 2 by saying he was taking her to Water Country, the location of their first date.
Thinking she was in for a day of water slides, Litchfield dressed in a bathing suit, summer dress, and flip flops, prompting Richards to hurriedly pack the sneakers and athletic wear more appropriate for skydiving and smuggle them to the car wrapped in a towel. When they arrived at Go Skydive Boston, a short drive from their home, Litchfield was caught by surprise but ready to go, Richards said. Because it was something they had talked about doing, she said she did not suspect a proposal.
The couple dedicated their jump to their friend Tim Engel, a paratrooper in the U.S. Army who passed away in March.
“He was always so excited about us being together,” said Litchfield, who choked up while talking about him. “We were like, ‘This one’s for Tim.'”

Alissa Litchfield and Ryan Richards pose after becoming engaged at Go Skydive Boston in Hanson earlier this month.
Litchfield and Richards each completed a tandem skydive from 8,000 feet, said MacKenzie, who jumped with the bride-to-be. Richards was waiting below, beside silver balloons and a banner that said, “Alissa, Will You Marry Me?” At about 1,000 feet, when Litchfield didn’t yet see the banner, MacKenzie felt compelled to help her out.
“I said, ‘Oh, gee, I wonder what those balloons are for?’ — trying to clue her in,” he said.
“I had no idea,” Litchfield said. “So when I was going down, I was just taking in the landscape. It’s so beautiful.”
Then she saw the banner.
“I just lost it and was absolutely happy sobbing,” Litchfield said. “I couldn’t believe it.”
“She was all emotional. She came over, and I got down on one knee,” Richards said. “I asked her very simply. [I said,] ‘I love you [so much], Alissa. Will you marry me?'”
“It was so sweet,” said MacKenzie, who said he has witnessed about 20 marriage proposals during the approximately 6,000 jumps he’s completed with his customers over the past eight years.
Litchfield’s best friend of 20 years, Kristina Tom, was standing nearby. Tom had set up the engagement spot while the couple was in the plane, prepping the banner, balloons, and champagne. She also kept the ring safe until Richards landed.
“I was in utter shock,” Litchfield said. “It took me 10 minutes to realize that my best friend was standing there too.”
The couple plans to marry next summer.
When asked how her future husband could possibly top this adventure, Litchfield said, “I don’t know, but I’m sure he’ll come up with a way to do it.”
Watch the proposal in a video shot by Tom: