Tinder and the Single Life: Coaches Are Booking Clients Who Thought They’d Never Have to Swipe in 2022

Updated: 07-2022

Many dating and lifestyle consultants are divorced women who want to provide the kind of guidance they found lacking when they were starting over.


“I’m not a selfie type of guy,” said Joe Ragusa, who hired Alyssa Dineen, the founder of Style My Profile.CreditCreditHolly Pickett for The New York Times

About five years ago, Joe Ragusa, a city Sanitation employee who works in the Bronx, got fed up with traffic and construction and all the other stuff and decided to move out of the city. He bought a house in the country, in the hamlet of Mahopac, and moved in with his girlfriend. Naturally, they broke up.

Now Mr. Ragusa, 36, has an hour commute to his garbage route in Throgs Neck. He often wakes at 4 a.m. to start his shift, he does not like the bar scene, and, well, dating has been a challenge. He has tried dating apps, like Tinder and Bumble, but the responses have been underwhelming.

“I’m not a selfie type of guy,” Mr. Ragusa said. “If I have 1,000 pictures, 998 are of my dog, and I’m squinting,” he continued. “I’ve been wearing the same clothes since high school.” He doesn’t meet many women at work. “How many people are out flirting with the garbage man?”


Joe Ragusa’s profile pic, before he asked for help.CreditJoe Ragusa

He knew he needed help. After an online search, he found Style My Profile, a company started by Alyssa Dineen, a fashion stylist who, at the age of 41, found herself divorced with two young children. Ms. Dineen is part of a network of women in New York City who have transformed their divorce experiences into careers, helping others navigate splitting up and starting over.

When Ms. Dineen divorced her husband of 13 years, she hadn’t dated since the 20th century. Dating apps felt awkward.

“It was like a foreign language. A friend helped me — she held my hand through it,” Ms. Dineen said. “I realized so many people didn’t have that. People’s bios were horrible. They were good-looking but put up selfies in the mirror with their shirt off.”


Ms. Dineen, left, and Michiko Boorberg help Mr. Ragusa perfect his look.CreditHolly Pickett for The New York Times

After two years, she met a mate. But she almost didn’t write to him, she said, because his photos were terrible. It sparked a business idea.

Drawing on her experience styling models for photo shoots, she started Style My Profile in 2017. Ms. Dineen, who lives in Brooklyn, now has clients all over the country, whom she helps through email and video chats to buy clothing, edit bios and get photos that “make the person feel good, not make them look like a different person.”

For $300, Ms. Dineen’s baseline service is a one-hour call during which time she’ll edit bios and advise on photos. For a more thorough overhaul and consultation, the fee can go up to $3,000.

Amy Nobile, 49, takes things a step further. When Ms. Nobile split from her husband of 20 years in 2018, she “attacked” dating “like a job,” she said. The co-author of four books, including “I’d Trade My Husband for a Housekeeper,” scheduled four to six dates a day — coffee, drinks — until she met the man that she is now happy with, she said.

But she had friends who were struggling to click with people. So she started experimenting with writing text messages on their behalf.

“I found I have a knack for taking on people’s voices,” she said. She had become a modern-day Cyrano de Bergerac. A business, Love, Amy, was born.

“People get weird on these apps. They don’t even talk like themselves,” Ms. Nobile said. “After three or four meetings with my clients, I can banter as them, I can be them.”


Mr. Ragusa’s makeover continues at Bloomingdale’s. CreditHolly Pickett for The New York Times

Ms. Nobile finds matches and sets up dates, taking over the initial back-and-forth messaging (with clients looking over her shoulder.) She hands everything over once dates are set.

“It takes away the emotional roller coaster that people get on,” Ms. Nobile said. “People ghost you; it’s depressing, and people will walk away from it. I can maintain the dating rhythm for months until they can get used to it.”

Ms. Nobile recently worked with Jenni Luke, 46, the chief executive of Step Up, a nonprofit mentorship program that links professional women with girls from under-resourced communities.

“I don’t even accidentally bump into a man at my work,” said Ms. Luke, who is single and who has never married.

During the first month working with Ms. Nobile, Ms. Luke said, she went on eight dates, more than she had in a year of swiping and texting on her own.

Ms. Luke is not worried about telling men that they were initially communicating with a hired gun, she said. She credits Ms. Nobile with willing her confidence forward.

“There’s not a ton of stuff said,” Ms. Luke explained. “It’s a little back and forth and then, Hey, I’ll call you, or let’s get a coffee.”

Some men — fathers, in particular — need an overhaul of their real life before they can start to tackle the virtual one. This is the focus of Lisa Dreyer’s business, the Divorce Minder.

Ms. Dreyer came up with the concept after experiencing what she calls the “2008 financial crisis effect.” In 2009, as she and her husband were splitting, so were six couples whom she knew. Her male friends, she said, were successful professionally, but began regressing as humans.

“They can run a trading desk, but six months later they’re still eating off paper plates,” Ms. Dreyer said. They were coming home, she continued, “to an apartment that would have been depressing at age 25.”


“How do they feel?” Ms. Dineen asked Mr. Ragusa. “Snug,” he said. “I’m used to wearing everything big.” CreditHolly Pickett for The New York Times

So for divorced men, Ms. Dreyer provides full-service home management. She will find and decorate an apartment, get laundry and groceries delivered, work with the ex-wife to organize a digital calendar, buy birthday presents, plan vacations, hire a nanny and a cleaning lady, and buy extra sets of pajamas for the children.

Newly divorced women have their life issues too, like simply asking for help or advice, which can affect their dating confidence, said Liza Caldwell, a former stay-at-home mom from the Upper East Side who divorced 10 years ago. She runs SAS For Women, which provides coaching and support throughout the divorce process. “You have to reinvent,” Ms. Caldwell said. “What are you going to be in the new life?”

Ms. Caldwell knows about this firsthand. When she entered the dating scene at age 44, the “online meat market” did not appeal to her, she said. “For two years I kept waiting to be introduced to someone I could go out to dinner with. It never happened.”


Mr. Ragusa’s current profile pic. “I’m hoping to find the right one, someone special,” he said.CreditHolly Pickett for The New York Times

As a divorce coach, Ms. Caldwell thought her profile looked great, but Ms. Dineen, of Style My Profile, whom Ms. Caldwell had hired, insisted that she get new photos. “It tripled my responses,” Ms. Caldwell said.

Ms. Dineen’s work with Mr. Ragusa, the garbageman, was more involved. Before he got new photographs, he would need a new wardrobe and some grooming.

On a rainy Sunday afternoon, Mr. Ragusa, whose shift was scheduled to start at midnight, drove to SoHo to meet with Ms. Dineen. After getting a beard trim, they hit Bloomingdale’s.

“Are you O.K. with me picking out some stuff?” Ms. Dineen asked.

“Sure, I’m game,” Mr. Ragusa said. “I’ll just gravitate to what I already wear: jeans with holes.”

After two hours, Mr. Ragusa emerged from the dressing room in a tight fitting cotton shirt and gray jeans.

“How do they feel?” Ms. Dineen asked. “Snug. I’m used to wearing everything big,” Mr. Ragusa said. “Don’t worry, you’ll ease into it,” Ms. Dineen told him.

Back at Ms. Dineen’s work space, Mr. Ragusa posed for some photographs.

Later he said he was cautiously optimistic that the time and expense would be worth it.

“Overall, not to sound corny and cliché, but I’m hoping to find the right one, someone special,” he said.

“I definitely have hope.”

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