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.)

(Speaking of singles: You can support this hyper-local blog with singles, hundreds, credit cards, PayPal, Venmo, even Zelle. Please click here to learn how to donate to “0688o.” Thank you!)

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

  1. Some people have “stick-to-it-iv-ness.” For example, I had the same dentist for 50 years (Dr Oliver on Center St.), the same barber for 43 years (Mario from South Maple & Fairfield.) Actually only five people have cut my hair. I’ve had the same wife for almost 44 years. I’ve only had one brand of coffee in my entire life; I had my first cup of coffee when I was age 44, and it was a Starbucks. I’ve never had a different brand. I’ve annoyed 06880 readers since 2011 or 2012, and have never read another blog in my life! I do applaud Jill, though, for identifying a “need” and filling that need.

    • Richard Fogel

      your funny

      • Eric William Buchroeder SHS ‘70

        You’re not. (but at least you’re staying on Dan’s topic thread)

        • Eric, Dr. Oliver was my dentist from 1967 to 2017, and where ever I lived during those 50 years, I returned to Westport to go to the dentist. I traveled from Florida, New Jersey and Maryland to keep a dental appointment with him! I even wrote an e-mail last week, to his daughter, Kim, and his wife, to keep in touch with them.

  2. Please stop 🥲

  3. Meanwhile, dontcha think it’s sort of strange that so many married folks can’t stand each other when they actually have to be TOGETHER? WTF brought ’em together in the first place…just sex and money….can’t be, can it?

    • Richard Fogel

      what’s wrong with sex and money ?

      • Well, Richard, seems something’s wrong with it since it does not, by itself, hold up under mandated togetherness …..apparently.

        • Richard Fogel

          Dan your very smart. What is the secret.?

          • Been married 60 yrs, Richard, and I still ain’t got no answer…but bowing to sex as I do, and weak kneed as I get in the face of money, I dont think they cut it over the long run.

            • Richard Fogel

              I agree I’ve been married 44 years. My experience is to keep emotions in check. Be kind. Don’t hold grievance. Forgive. Don’t keep a grievance lust

        • Richard Fogel

          As the wise person you are what’s the answer ?

  4. Let’s discuss what works. Be kind and supportive of others. A kind word goes a long way. Everyone sometimes argues, but one can argue without getting angry! Be humble. People like humble people. A sense of humor also is very positive in relationships.

  5. Dan let’s go back to three😂

  6. If Tom doesn’t mind, I’d like to make another comment about JillianIt. There is very fertile ground in a 25 mile radius of DC. For example, Arlington, Va has more single, educated young people than any place in the country. (Of course we’re talking percent of population.) The young people come from North Dakota, Kansas, Arizona etc… and they come for government work and don’t know anyone in the area! If she (Jill) ever considers a second location, may I suggest “JillinitinDC.”

  7. Dan What’s with the advertising for a dating service. Let’s keep to the topics that make you as effective and Germaine as you have been. If I wanted ads I can just open the internet.

    • Not an ad. I got an email from Jill about what she’s doing. I followed up, and found it intriguing. “06880” tries to cover all aspects of life in Westport. Divorce, singles and dating are all important parts of life here, to a segment of residents. Not all stories resonate with all readers — nor should they. Feel free to recommend stories you’d like me to cover.

  8. Doesn’t it cost $3,000 to get set up at a mixer with six dating candidates? Mind blown.

  9. I have one last comment left. What this woman is doing is actually needed! This posting really piqued my interest and I passed it on to someone in the medical field at the University of Maryland Medical Center who found it interesting. Shame on anyone who thinks this posting is somehow inappropriate!

  10. David J. Loffredo

    Some of you should send Dan a monthly check for the mental health outlet he provides you. Maybe he can create a “private” blog that the rest of us don’t have to read.