Hannah O’Brien-Rupert grew up in Westport. Her schools were Coleytown El and Middle, Bedford Middle and Staples (Class of 2001).
Then came Emory University, Georgetown, and important positions at Bear Stearns. She landed on her feet after the firm collapsed, and is now a credit analyst with Raymond James.
Conrad DeQuadros was born in Vancouver. He was 3 when his family moved to Toronto, 5 when they went to Perth, Australia and 9 to Oman. He finished high school there; attended college back in Canada, and ended up at Bear Stearns too.
When that imploded he founded an independent economic consulting firm with his former boss. It’s now the 3-person RDQ Economics.
Hannah and Conrad met at Bear Stearns. Even before marrying in 2010, they talked about where they’d live when they had a family. They had an apartment in midtown Manhattan, not far from work, but realized it’s tough (and very expensive) raising kids in the city.
Hannah said, it’s Connecticut — no ifs, ands or buts. Conrad had no ties here, but had visited friends and played golf in the area. He liked it.
They looked briefly at Darien, more closely in Westport.
“The whole process happened quicker than we thought it would,” Conrad says. “We really started seeing ourselves living here.”
They bid on 2 homes, on Compo Road North and Arrowhead Road. Neither worked out.
Eno Lane did. They got a good mortgage rate, and 2 years ago became Westport homeowners. Hannah says, “I could never see myself living anywhere else.”
Her mother laughed. “You didn’t always love it when you were living here,” she teased.
“I was 14!” Hannah retorted. “Of course I complained!”
She and her husband expected to use their Westport house only on weekends. Within 6 months of closing, however, it became their real home. “The apartment was just a place to sleep,” Conrad says. “This is such a different pace here in Westport. We feel so much more relaxed.”
“We’re very social, but ‘home’ is important to both of us,” Hannah explains. “This is a space where we feel comfortable. An apartment is temporary. No matter how much you decorate, there’s always a lease.”
The couple love entertaining, and eating out. They enjoy trying new restaurants here. Hannah says, “We don’t feel like we’ve given up anything.”
Last year they rented a kayak from Down Under. Paddling up to the Post Road bridge and back, they felt as if they were on vacation. “It was an amazing 2 hours,” Conrad says. “We just saw everything from a different perspective.”
Perspectives are interesting. Hannah’s is that Westport began changing in the early 200s — when she was in college.
“Things started getting fancier. There were more chain stores downtown,” she says.
But Westport still has plenty of charms — and the couple is happy to share them. “It’s not too difficult to convince friends to come out from the city,” Conrad notes.
Hannah is still close to many Staples friends. Some are recently married; as they start planning families, they too think about moving back here. Those who are single or not yet settled down have a harder time envisioning life in the suburbs, Hannah admits.
Returning to her hometown is not without surprises. Hannah has been shocked by poor driving habits. “We all have bad days and busy lives,” she says. “But I don’t see how so many people blatantly ignore traffic laws, and common courtesy. Sometimes I’m petrified.”
Conrad is amazed that people blithely take up 2 spots at the dump, where parking is at a premium. He’s also surprised at the lack of sidewalks. He’d love to walk to the station, but — especially in winter — feels he’d take his life in his hands on busy Saugatuck Avenue.
Yet those are minor quibbles. A big and pleasant surprise, according to Conrad, is “how quickly we’ve become comfortable here. Almost immediately, we realized we didn’t want or need our apartment. This is home. That speaks a lot about the type of town it is.”
And, of course, there’s the beach.
“We absolutely love it,” Hannah says. “We’ll take a quick 20-minute walk at night. On Friday it’s a great way to start the weekend, and on Sunday we get ready for the week with a potluck dinner with friends. Some nights we’ll just take a quick 20-minute walk. It’s a great stress reliever.
“Even in January, we’ll put on our coats and go down. I can’t imagine not having the beach.”
Even if, when she was 14, Hannah could not have imagined living — with an international husband — back in her old hometown.