Timing is everything: Longtime friends kept coming back to each other – and Alexandria

Timing is everything: Longtime friends kept coming back to each other – and Alexandria
Joey and Caitlin Kestermann. (Photo/Deb Lindsey)

By Leslie Golden | lgolden@alextimes.com

“I was dating his roommate,” Caitlin Kestermann confessed with a sheepish grin.“And when Joey walked into the room, I saw him and just thought ‘Ohhhh nooooo.’”

And so begins the story of how two people spent years living in the same town, socializing with shared friends, hitting all the same spots and spending time in relationships with other people all the while destined to be together. Nearly 20 years later, they’re happily married with three beautiful children. But first, about that roommate.

“Hey, you’re getting into the nitty gritty here,” Joey Kestermann teased as he settled onto the couch. The dog meandered into the room and their son Tucker climbed onto his lap. Joey and Caitlin are relaxed, playful and fully immersed in their life as a family of five. But it took years of missed moments, inopportune timing and unspoken connections for the couple to get to where they are today.

Though Caitlin was raised in Alexandria and Joey hailed from Dumfries, he was the one who ended up in Alexandria attending Bishop Ireton while Caitlin traveled to Arlington for school at Bishop O’Connell.

“On the weekends, when I was spending time with friends from growing up, I’d hear about Joey. A lot of my friends knew him from BI, so we kind of ran in the same circles,” Caitlin remembered.

But it wasn’t until that afternoon in 2005 when she saw him for the first time that she knew she was in trouble.

By then, Joey and Caitlin had graduated from college and settled back in the Alexandria area. They shared mutual friends and had heard of each other over the years. Whether single or casually dating, Joey just couldn’t stop thinking about her.

“When I first talked to Caitlin, something sunk in… and it never went away,” Joey said.

Years passed, relationships came and went until finally in 2010 they saw each other again. They were both invited to attend a friend’s birthday party and instantly connected.

“It was a big party in downtown D.C. and we were both there,” Caitlin said. “I immediately noticed Joey when I walked into the bar, but there were also old friends that I hadn’t seen in a while, so I wasn’t really paying attention to him. And then as our group went outside and people were just standing around talking about where to go next, he walked up to me and asked, ‘Do you want to get out of here?’”

They skipped the afterparty and caught up with each other or the rest of the night at a bar nearby. They were both dating other people at the time.

“We’d keep up with each other. We would talk, message each other or text. But nothing ever happened,” Caitlin shared.

“I can sum it up relatively well: I think what happened is that there was always something there,” Joey said. “Even when we were dating other people or involved in our own lives, even when she moved all the way across the country to California, there was something there.”

“It was funny. Even in California, yes, we would still exchange text messages and talk and send emails,” Joey recalled.

He once texted Caitlin while he was on a guys’ trip to Las Vegas: “I’m in Las Vegas. Can you come? Drive over and visit me.”

Caitlin never made it to Las Vegas. Another missed opportunity to connect.

By 2010, Caitlin felt the call to come home.

“When Caitlin moved back, I came to my senses finally. That was it. We pretty much immediately started dating,” Joey said.

Caitlin’s former roommate and lifelong friend Alison Henry was living with her when the couple finally got together. “When Caitlin and Joey finally became official, she was moonstruck. ‘Oh, Alison, I love everything about this guy.’ She couldn’t stop talking about him! It was over for her. I knew she was toast,” Henry said.

Three years later, Joey planned the ultimate Christmas surprise.

“It was the night before Christmas Eve, we were all going out in Old Town. I just told her we were going to meet a bunch of friends. But I had emailed all our friends and told them, ‘Hey guys, you really need to be at Columbia Firehouse tonight.’ So we parked nearby in front of the big Christmas tree in Market Square and I asked her to walk over to the tree to see the lights. It was perfect. I’d asked my sister to hide nearby to sneak a picture of the proposal.”

Joey’s sister Katie Larrabee fondly remembers the night.

“Joey knew getting down on one knee in front of the big tree would feel magical. Caitlin was totally surprised and it was very special for me to be able to witness that moment,” Larrabee said.

“Oh, it was so much fun,” Caitlin said. “After he proposed, I said, ‘Let’s go get a drink and celebrate!’ and when we walked into the restaurant, all our friends and family were there to surprise me. It was so, so special. Oh yes, I loved his proposal.”

Childhood friend Gillian Rice-Maupin also remembered that the engagement was special – and that she was not not at all surprised.

“It was a super fun night,” Rice-Maupin said. “It was always a tradition for our friends to get together around Christmastime and pop into different bars and restaurants around Old Town, so it was the perfect night to toast their engagement and celebrate them. Knowing Caitlin growing up and getting to know Joey during high school, I just knew they’d end up together. I don’t know another couple who passionately love each other the way those two do. They’re meant to be together.”

After many years of friendship, missed connections, courtship and an engagement, the couple wasted no time in saying “I do.” Less than a year after Joey popped the question, the couple married in September 2014 at Our Lady Queen of Peace Catholic Church in Arlington with a reception following at the Army Navy Country Club.

“We had the wedding in Arlington, because logistically it made the most sense for our guests to be able to walk from the church to my parents’ club,” Caitlin said.

“But it was an Alexandrian wedding. An Alexandrian affair. It was a reunion of sorts. Our friend, Alexandrian native and professional DJ Adam Smith, performed at the reception. We had one picture taken that was just for people from Alexandria,” Joey proudly declared.

Joey’s best man David Kaye recalled, “You just knew the were destined to get married.”

A honeymoon in Hawaii followed and by January they were expecting their first child.

“By the spring of 2015, we were house hunting and found our home in May. Our first child was born that October,” Joey said.

After years of circling each other socially and then forging a friendship, they were married with a home and a baby within a little over a year. Today, Joey works as the Service Director at MINI of Alexandria and Caitlin is an independent consultant. Their free time is devoted to family and friends and supporting their community.

Despite sometimes pondering a move to a different city, the couple found they couldn’t bring themselves to leave Alexandria.

“We always talked about how it would be fun to move somewhere else. This place … you just can’t get away from it. Because Alexandria is such a perfect place to live,” Caitlin said.

Joey expounded on what drew them to – and keeps them in – Alexandria.

“I would say it’s small enough that we know everybody somehow, some way. We have established so many friendships and our families are here. But there are plenty of people we get to meet who are new friends and there’s always something new for us here, too. The ties that pulled us to Alexandria were too strong to ever be anywhere else.”