Tag Archives: Divorce

In Post-COVID Singles World, Matchmaker Is “Jillin’ It”

Among the many casualties of COVID: marriages.

Forced to spend all day, every day together, many spouses skedaddled. The reasons varied, but the results were the same. Tons of single Westporters have joined those who were already divorced, or never married.

The good news: What they look for in a new mate is not what they previously sought.

“I used to always hear, ‘They’re just looking for my money or status,'” Jill Dunn says.

“These days, people don’t care about superficial qualities. Coming out of COVID they want true compatibility, a connection on a deeper level. They want love. There’s much less checking the boxes of income or height.”

Jill Dunn

Dunn should know. The founder and “lead matchmaker” at Jillin’ It, she’s seen the Fairfield County dating scene evolve in the 8 years since starting the personalized, online-and-in-person service.

Plus, she’s been there herself.

Newly divorced in 2016, Dunn found it hard meeting single men outside of New York.

Leveraging her background as an event planner, she organized speed dating and mixers, in Norwalk and surrounding areas.

The business evolved into full-service matchmaking. Today her clients range “from 28 to 88,” she says, though most are men and women in their 30s and 40s. She works with LGBTQ as well as heterosexual clients.

She does not take her work lightly.

“I understand the raw, empty space crated when you’re single,” says Dunn. “That’s especially true with people who are divorced or widowed, whose space was once occupied.”

Many new singles have “forgotten how to date” — just as Dunn had when she found herself single, in her early 30s, with 2 young children.

She helps her clients figure out who they are, and what they’re looking for. She’s a coach and a sounding board.

She solicits feedback after a date — from her client, and the client’s date — about what went well, and what did not, to help fine-tune subsequent searches.

“It’s an intimate, beautiful process,” Dunn says. Often, it last for 3 to 5 months. Then “they fly the nest. They don’t need me anymore.”

The first match is the most important. It’s always the same: “between the client and the matchmaker.” Dunn will not work with anyone she does not feel a trusted connection with. (“I’ll only date a 6-2 billionaire with a goatee” is a non-starter.”)

Once that trust is established, Jillin’ It is all in. She offers both private, personalized matchmaking and small group meetings.

“For me, it’s quality matches over quantity,” Dunn says. “I’d rather send a client on 2 dates in 6 months, than be a service that promises one date a week. You could do that yourself, standing in a CVS aisle.”

Working with a matchmaker is like hiring a personal trainer, she notes. “You open yourself up, because you want to grow. And the benefits are not just the hour in the gym or the dates you go on, but the new mindset you’re in.”

This time of year — between Thanksgiving and Valentine’s Day — is the busiest for matchmakers, Dunn says.

And the hardest for singles.

The world is filled with Valentine’s Day images.

“People don’t want to go through the holidays alone. They’re surrounded by so many images of love and partnership.”

The good news is that “as you’re looking for someone, they’re looking for you.”

Still, she says, “you have to put yourself out there.” It doesn’t have to be with a matchmaker: “Just go to events in the community.”

But — in a town filled with post-COVID divorced people, and those who have never been married — she sure can help.

(For more information on Jillin’ It, click here, or email hello@jillinit.com.)

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COVID And Divorce: Carole Orland Splits The Difference

The crucible of COVID drew many couples together.

Spending much more time than usual together, sharing parenting and household and professional duties like never before, they found strength and bonds that may have frayed over the years.

But the pandemic also caused many marriages to founder.

Stuck at home, without the usual distractions of offices and friends, some couples grew apart. Partners magnified their spouses’ flaws — real or imagined. Add in kid issues, mental health challenges and more, and the stresses mounted.

Maybe they had talked about divorce before the virus. Maybe not.

Either way, Carole Orland says, they’re talking about it now.

She should know. A partner at Westport-based Broder Orland Murray & DeMattie, she — and the firm — specialize in family law.

Which often means “divorce.”

Carole Orland

It sounds like a difficult specialty. But, the Worcester native and longtime Westport resident says, it is “an opportunity to help people who are in a bad way. It’s rewarding to see the process. By the end they feel better about themselves and their circumstances. They’re ready for their lives to really take off.”

Orland also likes the chance to be involved in other areas of law, like trusts and estates, and torts. She has a wide range of clients — in finance, business, sports, entertainment and blue-collar jobs — and learns something new in every case.

She learns about law. And she learns about human nature.

Is it depressing?

“That’s not the right word,” she counters. “It’s sad, sometimes. You see emotions, afflictions, addictions, abuse — bad stuff. My challenge is to get them to a better place. It’s not just about the divorce itself. We don’t just drop them off at the end.”

COVID shut down her office in March 2020, as it did many others. But they reopened in mid-May. Courts were closed; remote proceedings had not yet begun.

But the floodgates opened. And she has been busy ever since.

The pandemic changed how divorce looks, Orland says. As more fathers work and spend time at home, child custody arrangements evolve.

Employment is different too. COVID caused some people to reassess their work. “High flyers may not be in jobs that are as lucrative now,” Orland notes. “And other people lost their jobs.”

At the same time, people used the pandemic to move to higher-paying careers. Others found themselves in industries, like real estate, which boomed.

All of those situations force new looks at divorce settlements already in place. That’s even more work for Orland.

Not all of her job involves splits. She also arranges pre-nuptials. Marriages declined during the worst months of COVID. Now there’s a rush to the altar — and more clients.

“We were crazy busy before,” Orland says. “Now it’s really insane.”

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