Amy Osmun ended up sat next to stranger Mike Gilberstadt on a flight from the US to Amsterdam. They hit it off right away, and the course of both their lives was changed. Illustration by Leah Abucayan/CNN. Photos courtesy Kelli Gase and Amy Gilberstadt.
Amy Osmun assumed she’d never see Mike Gilberstadt again.
They’d met only 10 hours before. Now they were standing in Amsterdam’s Schiphol Airport, facing one another, both putting off the farewells. But time was ticking. They were both set to catch connecting flights – Amy to Scotland, Mike to Greece.
“I guess we have to say goodbye,” said Amy, reluctantly.
In a gesture of farewell, Mike leaned in to hug Amy. He kissed her, briefly, on the cheek.
Then Mike readied to leave, adjusting the bag on his shoulder. He was about to turn away when Amy spoke:
“Is that all I’m going to get?” she said, smiling.
Even as she said it, Amy knew this was a moment she’d remember.
“That’s when he gave me a real kiss,” Amy tells CNN Travel today. “It was absolutely electric.”
For a moment, Amy and Mike stood, kissing, amid the crowds of travelers at the airport. And then it really was time to say goodbye. Mike took Amy’s number, writing down her details on a scrap of paper. Then they went in different directions.
As Amy walked away from Mike, she tried to make sense of what had just happened. She never usually spoke to strangers while traveling, let alone kissed them. And she couldn’t figure out how her airport embrace with Mike fit into the wider context of her life.
Was Mike just a stranger she’d quickly forget? Would this become a funny story someday? Would she always wonder what could have been? Or would she look back and feel sadness, regret?
As Amy lined up at her gate, she tried to shake herself out of her reverie and swipe Mike from her mind. After all, she wasn’t just traveling to Scotland for a vacation — she was visiting someone. And not just anyone: her boyfriend.
Mike couldn’t be someone, Amy told herself, because she already had her someone.
An airplane encounter
Amy and Mike met on March 23, 2006, on an airplane about to depart Los Angeles International Airport.
Back then, Amy was a 24-year-old trainee dietician at California State University, flying to Scotland for spring break.
She’d ended up with the middle seat – an unenviable prospect for a long-haul flight. But while there was someone sitting next to Amy by the window, there was no one sitting in the aisle seat.
“It looked like I had an empty seat next to me for the long-haul flight – so I was pretty excited,” Amy recalls today. “And then I swear, right before the plane doors closed, he came sauntering down the aisle.”
“He”, of course, was Mike — who is, by his own admission, “not a punctual man.” He was the last person to board the plane, and he bounced into the empty seat next to Amy, who couldn’t help but roll her eyes.
“I was not impressed in the moment, as I faced a 10-hour flight squished in a middle seat,” Amy recalls.
But then Mike apologized – half jokingly, half sincere – for ruining Amy’s flight. And then, noting her eye mask and travel neck pillow already wrapped around her head, Mike – half jokingly, half sincere – offered Amy his shoulder to sleep on instead.
Amy smiled despite herself.
Later, once they were in the air, when Amy’s food choice arrived and looked less-than-edible, Mike insisted she help herself to his meal tray.
As she picked food off his plate, Mike and Amy started chatting – realizing they were a similar age, both living in Southern California, both interested in travel.
Amy thought Mike was funny and self-assured – and while she noted he tried to mask it under his jokes and bravado, he seemed kind. Feeling comfortable in his presence – and desperate to sleep – Amy accepted Mike’s offer of sleeping on his shoulder.
Several hours later, Mike and Amy landed in Amsterdam. As they disembarked the airplane, Mike suggested they grab a coffee together.
First in the coffee line, and later as they walked through the airport, Amy and Mike continued chatting. Amy noted how easy conversation was – even though they barely knew one another and were both bleary-eyed from the overnight flight.
And then, somehow, they ended up kissing in the middle of Amsterdam Schipol Airport.
“I thought I’d never see him again,” says Amy. “So I was like, ‘Why not go out there a little bit?’”
From long haul to phone calls
As for Mike, he’d liked Amy from the moment she scowled at him, eye mask perched on her head, as he boarded the plane at LAX. Throughout his time in Greece, Mike regularly replayed the airport kiss in his mind, hoping he’d see Amy again, wondering if and when he should get in touch.
Meanwhile Amy was enduring a “disastrous” visit with her long-distance boyfriend. She left Scotland single.
The break-up wasn’t really anything to do with Mike, says Amy today. She just realized this particular guy wasn’t right for her.
Back in California, Amy returned to her classes and doubled down on her studies. From time to time, Amy’s thoughts drifted to Mike – on their immediate rapport, on the airport kiss – but when he unexpectedly phoned her one day and asked her out, Amy said no. She was still reeling from her break-up and didn’t want to jump into anything new too quickly.
But over the next several weeks, Mike kept calling. Soon, Amy and Mike were chatting on the phone for hours at a time.
Mike’s roommates teased him about these lengthy calls, but Mike laughed off their jokes. He enjoyed talking to Amy, and she liked talking to him too.
“Mike was still just as charming as he was on the plane and at the airport,” says Amy. “So I finally took him up, and we went on our first date.”
That first evening, Amy and Mike met up for sushi and then went for a walk on the beach which turned into Mike giving Amy a piggyback ride. They collapsed onto the sand, laughing.
Later, back at Mike’s apartment, Amy marveled at the fact Mike’s television set had TiVo – a recording device that allows viewers to record live television to watch later.
Right away, Amy wrote down a list of her favorite TV shows and asked Mike if he could record them on her behalf. Amy was genuinely excited at this prospect – but it was also a bit of a ruse: if Mike was recording Amy’s favorite TV shows, she’d definitely be returning to watch them.
A week or so later, Amy and Mike enjoyed their second date at the themed dinner entertainment venue Medieval Times. Afterward, back at Mike’s apartment, they caught glimpses of distant fireworks illuminating the skies at Disneyland.
Over the next weeks, Amy and Mike continued meeting up regularly.
“A month or so in I had met his parents,” recalls Amy. This felt especially significant because Amy had never met her previous boyfriend’s family or friends.
There were other signs that Mike was in it for the long haul.
“He let slip that he had told a friend that he thought he was going to marry me,” recalls Amy.
Nevertheless, Amy worried her happiness with Mike had an enddate. She was set to leave the US for the UK for several months as part of her dietetics degree.
Amy worried her new relationship wouldn’t survive this distance, and she debated what to do, eventually ending things with Mike before she left for the UK.
Or, possibly, Mike ended things with Amy.
“He still maintains that he was the one that broke up with me, but I distinctly recall having a conversation with a friend just before about if I should break up with him,” says Amy.
The truth was both Amy and Mike were concerned about the impact of long distance on their fledgling relationship. Mike didn’t want Amy to leave, but Amy wasn’t going to abandon a great career opportunity.
They both – reluctantly – came to the conclusion the relationship must have run its course.
“So we broke up,” says Amy. “But we stayed in touch.”
Staying in touch
As soon as Amy left, Mike was flooded with regret. He found himself wishing he could have gone to the UK with her, and he thought about her often.
Amy missed Mike too. They kept up to date on one another’s lives via email and the occasional phone call. Social media was still in its infancy back then, so Mike also resorted to old school methods, sending heartfelt cards to Amy across the Atlantic.
Today, Mike jokes that this “never happened.” He’s not generally prone to putting pen to paper, and rarely sends cards to anyone on any occasion.
But Amy has the proof – she kept all Mike’s long distance correspondence, including a Valentine’s Day card sent to her in February 2007.
“It was fate I met you,” reads Mike’s message in the card. “If I wasn’t tied to Orange County, I would follow you anywhere. But most of all I wish you all the happiness in the world. You’ll always be my Valentine.”
Not long after Amy returned home to California that spring, she reunited with Mike. They picked a pointedly non-romantic spot for the reunion: Target, in San Diego. Amy was shopping with a friend of hers, and Mike came along too. The group walked around, browsing, laughing and joking.
“It was one of those Targets with two floors,” recalls Amy. “So you have a cart elevator – I was super excited about that.”
Amy was also excited to see Mike again. And it was clear he felt the same way. The two kept stealing glances across the Target aisle.
Within days, Mike and Amy were a couple again.
Moving forward
From then on, Amy and Mike’s relationship was unwavering and solid.
“Once we got back together, we were together,” is how Mike puts it.
Amy finished her studies and started working as a dietician in a hospital. She and Mike moved in together.
Then, in late 2007, Amy and Mike went on a trip to Ireland and Italy. While on a stopover in Venice, Mike asked Amy to marry him.
“We get in that gondola and then under the Rialto Bridge he popped down on his knee on the gondola and proposed,” Amy recalls.
She wasn’t expecting the proposal at all, but Amy was thrilled, and said yes immediately.
“It was a fun surprise,” says Amy. “And we got to spend the rest of the trip engaged, which was fun.”
Amy remembers excitedly phoning her parents and sister, discovering Mike had let them know his intentions before the trip. They were thrilled for her too.
Back home in the US, Mike and Amy started planning their wedding for the following year. That’s when they realized their parents shared a wedding anniversary: November 1.
As a nod to that coincidence, Amy and Mike got married on November 2, 2008. Amy took Mike’s name, becoming Amy Gilberstadt.
During their ceremony, Amy and Mike toasted their parents’ long marriages and their own future. The heartfelt speeches from friends and family also included several references to Amy and Mike’s cinematic airplane meeting.
Right after their wedding, Amy and Mike boarded another plane together – traveling to Hong Kong and then India for their honeymoon.
“We had a lot of fun,” says Amy of the trip. This kickstarted a pattern – each year, Amy and Mike committed to two big vacations a year. They’ve since traveled to destinations including Japan, China, Australia, New Zealand and Tahiti.
“Even when our son was born, he was only six months old and we were in the United Kingdom for a trip,” recalls Amy.
Amy and Mike welcomed their son in 2010. They were both delighted to become parents.
“I’d always wanted children – I wanted to have a son and named him after me, which I’ve done, so that they could know my pain of having their calls answered and their mail opened,” says Mike, laughing.
Mike and Amy later welcomed a daughter in 2013. The couple describe their two kids as “pretty darn fabulous.”
Over the years, Amy and Mike have enjoyed watching one another find their footing as parents.
“I can keep the play dates, the organizational stuff going. But I was not, and I’m still not, very good at playing,” says Amy to Mike. “You’re really good at that. I would give myself about five minutes of playing Barbies and I was like, ‘I’ve got to go do something else.’ And you could be up there for ages with our daughter.”
“We had a whole world going on,” says Mike of his years playing Barbies with his daughter.
In recent years, Amy and Mike have also supported each other through tougher times. In 2020, Amy’s aunt passed away suddenly and her mother became extremely ill with Covid-19. That same year, Mike’s mother was diagnosed with lung cancer.
“That was a really tough time,” says Amy.
She and Mike rallied together around their loved ones and “survived loss and illness,” as Amy puts it.
“We’re still going strong,” she says.
Going strong
Today, Amy and Mike are forced on family, travel and adventures. The Gilberstadts recently headed to Alaska to catch the Northern Lights and then on to Vermont to see April’s solar eclipse.
“I had never seen a total solar eclipse before. So I wasn’t expecting much from that. But that was way more amazing than I thought it would be,” says Mike. “It was quite a celestial trip.”
“We had a blast,” says Amy.
Later this year, Amy and Mike hope to take their kids to Japan – an 11 hour plus flight from LAX. Amy and Mike joke that they still operate on long haul flights very similarly to how they did on that first flight over 18 years ago: Amy tries everything and anything to get some sleep, while Mike will always offer her his shoulder or lap.
The main difference is Amy and Mike have since perfected “playing with travel points,” as Mike puts it, and like to travel in the premier cabins if they can.
And they always avoid the middle seat – even though it’s what brought them together all those years ago.
Today, Amy and Mike look back on their first meeting with a mix of joy, surprise and gratitude. For Amy, it makes her a little “teary-eyed” as she puts it, to reflect on their random meeting and everything they’ve been through since.
“I can’t believe it,” she says.
As for Mike, he possibly said it best in one of his other rare forays into card writing – on Amy’s first Mother’s Day in 2010:
“Who would’ve thought all these things would happen,” he wrote. “Hopping on that flight to Greece was the best and most rewarding thing I have ever done.”
