Lynn Shanahan loved Westport, Conn. It was restful, beautiful and close to New York—an ideal escape from the city on sticky summer days. And then she moved there.

 

“I was standing on the train platform in the dark at 6:15 a.m. when I realized I had made a mistake,” she recalled.

 

“We had this vision of the perfect life,” said Ms. Shanahan, the CEO of apparel conglomerate Kellwood Company, describing the tranquil suburban existence she’d imagined: The long morning walks, the serene return in the evenings. Even the move was a breeze—she and her husband already owned a house in Westport, which served as a beloved, quasi-bucolic summer escape for the couple and their three children.

 

The reality was far less idyllic. The house and yard required constant tending, weekly grocery shopping trips proved a chore compared to casually picking things up throughout the week and dinner options after 9:30 p.m. dwindled to pizza or Chinese takeout. Fine every now and again, but “when you’re 50 years old, you’re kind of over that.” Worst of all was the commute, which quickly solidified into a dreary pattern: “Get back, go to sleep and get back on the train again.”

 

The Shanahans couldn’t return to New York fast enough. Once their oldest daughter finished out her last two years of high school in Westport, they fled back to their apartment in Carnegie Hill, which they’d rented to a family that was itself enacting a suburban exit.

 

For many a New Yorker, moving to the suburbs is more a compromise than a cause for joy, a decision that’s made all the more difficult by its grim finality—you’d often think moving trucks were crossing the River Styx rather than the Hudson—done with the understanding that a return to the city, if there ever is one, is at least 15 to 20 years in the future. But a small percentage of newly-minted suburbanites double back in a matter of months, desperate to return even if it means taking a loss on a house or squeezing back into a tiny rental again.

 

For some, even a brief exposure to the realities of suburban life—shoveling snow and having to get into a car to pick up the dry cleaning or takeout—is sufficiently traumatic to cure longings for expansive lawns, swimming pools and vast storage spaces.

 

“Whenever I hear a client is moving to the suburbs, I wish them well and figure I probably won’t ever see them again,” Corcoran broker Deborah Rieders told the Observer. “But more often than you’d think, I get a call—‘It’s not working’—a few months or a year later.

 

“Maybe they’ve lived in Brooklyn for 10 or 12 years, they hear about a lot of people moving to Maplewood and they think it will be just like Brooklyn,” she continued. “Then they move and they don’t like the community or lack of community, they don’t like the fact that they can’t walk, they miss their friends. They don’t realize how alienating it will be until they get there.”

 

But whatever compels city-dwellers to beat a hasty retreat from the comforts of suburbia, they share a common trait—they not only want out, but immediately.

 

“Usually they move straight into a rental while they’re looking,” said Ms. Rieders. “Once they’ve made the decision, they don’t want to wait.”

 

Like many penitent suburbanites, Scott A. and his wife Leah were lured out of the city by a friend, in their case one with a spacious apartment in Jersey City. Their building on East 76th had been bought by Sloan Kettering and they were looking for a new place when the friend told them about a two-bedroom available on the top floor of her building. At $2,456, it was both a little bit cheaper, and a little bit larger, than their current place. Plus, the development had its own dog park, a big plus for two people with a large husky mix. Of course, Jersey City isn’t exactly a suburb, but it may as well have been for the long-time Upper East Side denizens.

 

“It seemed a bit like living in Greenpoint, it was like, ‘What’s the difference?’ ” said Scott, the CTO of a software company who was, at the time, doing most of his work from home. “Then I discovered what the difference is. You’re in Jersey.”

 

Small dissatisfactions quickly added up. “Little things that you don’t even think about at first, like no 24-hour diner within walking distance,” he said. They were the only people who used the dog park in their development. The novelty of eating at places like Joe’s Crab Shack soon wore off. And then they found out that none of the hospitals in Jersey City accepted their health insurance.

 

When the building raised their rent to $2,700, they called their broker, Cyla Klein at Citi Habitats, who herself had spent decades as a Long Island exile raising four sports-obsessed boys—“You do things you’d never think you’d do when you have kids.” Ms. Klein found them half-a-dozen places on the Upper East Side for comparable rents. When we spoke, the couple had moved into a $3,010 two-bedroom in Gracie Square less than a week before. “It’s like we never left, like I woke up from a dream or something,” Scott said.

 

Did he like anything better in Jersey City?

 

Such is the mistake made by people who drive up to the suburbs on weekends to house hunt, particularly in spring months like April or May, according to William Raveis managing director Kathy Braddock. Few actually practice the commute before moving—she recommends going to a hotel in the town on a Sunday night and commuting to work on Monday to truly get a sense of what it will be like. A commute that looks like 40 minutes on paper may actually end up averaging double that.

 

Even then, there can be unpleasant surprises. Many families move out after the kids finish school in June, when the days are long and they can enjoy a drink on the patio as the sun sets. Then the winter comes.

 

It’s also common for people to think that they’ll save vast quantities of money, only to discover that the cost-of-living difference is marginal. Taxes are often very high in New York suburbs and for commuters, the cost of monthly MTA passes must be added to monthly train and car expenses. And whereas rent is a fixed expense, much like common and maintenance charges, owning a house means lots of unplanned costs—from small plumbing hiccups to major roof jobs, not to mention the expense of yard work, alarm systems and pool maintenance.

 

“It’s a big transition, and it’s not necessarily a less expensive transition,” noted Ms. Braddock. “Are you used to really taking care of a home? People in New York are usually not.”

 

Saving money is not the only fantasy. New Yorkers accustomed to schlepping groceries on foot, hauling strollers up and down the subway steps and waiting in long lines often imagine a suburban life of preternatural ease only to discover that in the suburbs, they’re taking the car to the train to the subway just to wait in those same lines.

 

“The challenge for most people is logistics,” said Douglas Elliman broker Gabriele Sewtz. “There are very few people who don’t like some aspects of living in the suburbs, but the city is so convenient. You just walk two steps and get what you need.”

 

Sellers who used to live in doorman elevator buildings have a particularly hard time adjusting, she said. “It’s not only difficult to live in a different neighborhood, but it’s difficult to take out your garbage. And no one is there to take out your mail; you actually have to get in line at the post office. It’s not that you can’t do it, but like commuting, all things eat into quality time.”

 

It’s a more complicated life, observed Halstead broker Deborah DeMaria, who rented out Ms. Shanahan’s apartment and herself spent several years living in Charleston, S.C. Which isn’t a suburb of course, but it felt like it to Ms. DeMaria. She suddenly had a townhouse, a yard, two cars, school carpools to be scheduled, trash cans to be taken out and house sitters to be arranged when they went out of town. Strangest of all, she said, was that despite having a whole house to occupy, everyone hung out in the same few rooms.

 

“We had three floors, with a playroom on the third, but the kids never wanted to go upstairs by themselves,” said Ms. DeMaria. “A lot of time, people move because of space, but you’re only in one room at a time.”

 

She and her family moved to a three-bedroom Financial District a few years ago and her kids couldn’t be happier—their building has a pool and a billiard room. Indeed, as kids get older, a small Manhattan apartment with good amenities and nearby parks can actually be a lot less claustrophobic than a three-bedroom house on a cul-de-sac.

 

“People get so nutty about their children, they think, ‘Oh I have to do this for my kids,’ ” but they totally adjust,” said Ms. DeMaria. “If you’re fine in a two-bedroom apartment, the kids will be fine in a two-bedroom apartment. If you move to the suburbs, you have to do it for you.”

 

“The first time we put my son down on the grass, he cried,” said Tracy Beckerman. “We had to play recordings of city sounds to get him to sleep.” Ms. Beckerman lobbied her husband to move back from Summit, N.J., until they had a second child, at which point she accepted the inevitable. She subsequently vented her frustrations by writing a book—Lost in Suburbia: a Momoir, a blog, and newspaper columns.

 

A former TV producer-turned-stay-at-home mom, Ms. Beckerman said that one of the most difficult things for recent transplants is the one-two punch of losing their friends and in a lot of ways, their identity.

 

“When you live in a city as vibrant as New York, you don’t realize how much the city is your identity,” she said. She and her husband both had “cool jobs,” she said, they went out to restaurants every night, even with baby in tow—one of his first foods was sushi—and running together in Central Park. She loved her impractical Upper West Side duplex so much that when she was too pregnant to get up the spiral staircase, she told her husband she’d rather hook up a pulley system than move. Leaving behind all the things which she thought defined her, she wasn’t sure what did.

 

Plus, she had a terrible time making friends at first.

 

She recalled going to a neighbor’s barbecue where a group of women was animatedly discussing someone in the hospital for a miscarriage, who found out her husband was cheating on her and that she had an incurable form of cancer. “All these terrible things,” Ms. Beckerman said. “I finally said to one woman, ‘That’s awful. This is one of your friends?’ And she said, ‘No, it’s Victoria on Days of Our Lives.’ ”

 

After writing the book, she received hundreds of letters from other women who feel similarly displaced and her blog is a hotbed of discontent. Though the suburban mom-rage is such that Ms. Beckerman must often clean up the expletive-laden comments section. “It’s run on some family-family newspaper sites, so it can’t be all ‘What the fuck,’ and ‘Fuck that,’ ” she said.

 

Social isolation is, perhaps, the most common complaint of suburban refugees.

 

“I think what people miss most is the ability to go out, the opportunity and the options,” said Ms. Sewtz. “Even if people have a newborn and won’t be going out all that much, it bothers them that they are an hour away if they want to go to a show.”

 

One woman said that whenever she had dinner with friends, she was constantly checking her watch to make sure that she didn’t miss her train. Eventually, she started making all her dinner plans by Grand Central.

 

“When you have to look at a schedule, it changes your whole outlook,” said Ms. Klein. “All of a sudden you’re not willing to do things on the spur of the moment.”

 

Still, for all those who regret relocating, only a small number reverse the decision.

 

“I think two out of three have instant regrets, but no one likes to admit a mistake,” said Ms. Sewtz.

 

“Who could afford it?” shot back one friend when we asked him if he knew of anyone who did it.

 

“It’s hard to find rentals outside the city, so most people buy a house, and it’s not always easy to sell the house,” said Ms. Braddock. “Then there’s the question of whether the kids can get back into their schools. It’s hard to recreate your life in the city when you move out. It takes a lot of money.”

 

It’s not only re-selling the house, but also many of the furnishings, the yard maintenance apparatuses, one or both of the cars. Combined with the fact that real estate prices in the suburbs don’t appreciate as fast as prices in the city, many couples realize that they can’t even afford to reclaim the one-bedroom apartment they were so desperate to leave.

 

“I think people underestimate that it might be financially impossible to reverse the decision,” said Ms. Sewtz. “A few years ago I had a couple with a one-bedroom condo in Park Slope. They moved to Westchester, had a baby, typical story, then they called me up and said, ‘We want to come back.’ ” But the couple couldn’t afford to buy the two-bedroom they may have been able to get if they’d stayed in the city, so now they’re stuck renting one, trying to save enough to buy. If and when they do, she said, it certainly won’t be in Park Slope.

 

Shortly after Amy and Matt Kitt started renting in Rye, they contacted the broker, Steve Snider of CORE, to see if he could find a good-sized two-bedroom for less than $800,000.

 

But disappointed with the options—many of them were only a hair bigger than their old apartment—and expecting a baby, they felt but they had no choice but to stay. So they bought a house whose primary selling point, they say, is that it’s only a mile from the train station.

 

Even though they moved in June, they still spend three or four days a week hanging out in the city—dinners, Rangers games, visiting Amy’s parents in Brooklyn. “I can’t imagine not being part of the city,” said Mr. Kitt. “Even if we can’t come back until we retire.”

 

New York may be even further out of reach by then. “If you have the money to live in a $3 million apartment in New York, you have the means to come back, but if you’re a regular person who doesn’t want to leave the city, but can’t physically live in the city, I don’t think there’s any chance,” said Mr. Snider.

 

While it can be near-impossible for a couple like the Kitts to return to New York, those who do manage the feat say that it’s an easy transition: They hardly mind downsizing, learning to sleep amid the blare of sirens again or sharing their favorite greenscape with hundreds of other people.

 

“The noise at night was hard at first, but the adjustment happened really fast,” said Lynn Shanahan. “It’s such a joy to be home from work in 15 minutes. And I can’t believe I can just call a friend to meet for a drink.”

 

Best of all, living back on the Upper East Side, she can finally enjoy being in Westport again. “I’m back to being able to love the suburbs.”

 

*Correction: a previous version of this article stated that Deborah DeMaria lived in Battery Park City. In fact, she lives in the Financial District. The Observer regrets the error.