Tag Archives: singles

Death Of The Dinner Party: Westport’s Singles Culture

“06880” culture correspondent Robin Moyer Chung writes: 

Westport has a high rate of marriage — around 66% of the population. And when there are marriages, there are divorces.

Let’s begin with a question to married people: Why do you not invite your single friends to dinners and parties? Almost every single person mentioned this invitation situation.

“You just lost your marriage and now you have lost your friends,” one woman said.

“A very good friend told me casually over lunch about the 50th birthday party she had at her house just weeks before. We’ve been friends for years,” added another.

“I threw so many dinner parties, went to so many. Suddenly I was only invited to girls’ nights.”

Single men shrug it off, assuming their old “couple” friends align with their ex-wives.

One man, whose “social life evaporated” after his divorce, said, “I think many of the wives actually forbade their husbands from socializing with me.”

Why is this? Fear that divorce is contagious? Fear of odd numbers?

In lieu of invitations, married people eagerly offer their single friends advice about divorce, when to have sex and with whom, and how to improve dating profiles.

One person said, “I find that married women are sort of fascinated with the single life. Fascinated and scared by it.”

Westport is a couple’s town. It can be felt pretty much everywhere.

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Westport is a couple’s town … from proposal (she said yes!) to social life after the wedding. (Photo/Sunil Hirani)

At a restaurant, a woman and her children were seated at a high-top with one empty chair. After a long wait she asked a waiter for service. He said he’d been waiting for her husband to arrive.

“I think businesses around here could do a better job at making single women feel welcome,” she told me.

Another woman recalls a friend telling her: No offense, but my husband and I have been married 35 years, and its been great.

“I’m like, why would that be offensive?”

Loneliness is a familiar chorus. I heard, “A lot of things have changed, and it’s much lonelier,” “I think being single here, it is very lonely,” and parties and weddings are tough because “you don’t have an anchor.”

Of course, a few concede they also felt alone when they were married.

Women tend to feel more isolated than men. Men who work outside of town have more opportunity for outings and entertainment than women who work closer to home.

A surprising number of men meet other women while they’re still married; it’s often the catalyst for finally leaving a troubled marriage. But none that I spoke with met at a dinner party.

Which brings us to dating.

Dating is fun. Even when it’s bad it’s fun, because who doesn’t love a crazy dating story?

Finding dateable people is always tricky, but Westport can be “claustrophobic.”

Singles scenes at bars have not been as robust since COVID. Still, there are options.

The Spotted Horse used to be the go-to for determined singles on Thursday nights. Now it’s, well, not. One visit revealed a sedate crowd; a second pop-in, a corporate get-together.

Nômade is a “soft launch” bar, without the faint aggression of a singles scene. People tend to come in groups and, hopefully, mingle. Fridays and Saturdays are best for meeting people, and the crowd is typically respectful and well-mannered. (But women: You need to be a bit less shy.)

The Black Duck is a good option if you’re looking for a buzz and a hook-up. However, be wary of the person slipping you their phone number; they may be married.

Black Duck bar. (Photo/Robin Moyer Chung)

Gold Coast Connect meetings are for making business connections. Yet as they skitter through the evening, they become less business and more connect.

Dating apps: ugh. Pretty much everyone has tried one. Pretty much everyone hates them. “They’re a nightmare” is a common refrain.

Okay, they’re not always a nightmare. A number of singles have met “nice” people on them. Westport men have better luck with apps, in part because they tend to date women 10 to 15 years younger, so they swim in a larger dating pool.

Sadly, for every decent match there are hundreds of people trying to catfish, gold dig, ghost, insult, and ask for naked photos.

Nômade is also popular with singles. (Photo/Robin Moyer Chung)

A lot of non-single people suggest singles should volunteer, join clubs, take classes, and do stuff like that.

But no one I interviewed met people (other than friends) in those capacities. Of course, that doesn’t mean it can’t happen.

In sum, it isn’t easy being single in Westport.

In fairness, it’s not always easy being married, either.

If it were, there would be far fewer single people.

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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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