Darien New Canaan, CT May 2026

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L i l l e D e s i g n s i s a D a r i e n - b a s e d b o u t i q u e s t u d i o s p e c i a l i z i n g i n r e f i n e d e x t e r i o r s f o r

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Power, Presence & Possibility

There’s something powerful about a woman who knows who she is—and chooses to build something meaningful from that place.

This month, we’re celebrating exactly that.

Our Women’s Issue is dedicated to the women shaping Darien and New Canaan in ways both visible and behind the scenes. Founders, creatives, mothers, leaders, and connectors who are building businesses, supporting families, and strengthening this community every day.

Our story featuring Vela Motherhood introduces a concept many don’t even realize exists, a maternity concierge designed to guide families through pregnancy and early parenthood with clarity and confidence. It’s thoughtful, intentional support during one of life’s most transformative seasons, and a reminder that women don’t have to navigate it alone.

You’ll also find inspiration in Tanya’s style column, where she shares seven spring trends that actually work for real life because getting dressed should feel effortless, not overwhelming. Megan Schinella brings us her latest local favorites, highlighting the people and places that continue to make this community so special. And in Ask Leslie, we’re reminded that sometimes the most powerful thing we can do is ask for guidance and be open to receiving it.

Each of these features reflects something we believe deeply: when women are supported, confident, and connected, everything changes not just for them, but for the communities around them.

As you flip through these pages, my hope is that you see yourself in these stories. That you feel inspired, understood, and maybe even a little more empowered to take the next step, whatever that looks like for you.

Because this issue isn’t just about celebrating women.

It’s about what becomes possible when they’re fully supported in becoming who they’re meant to be.

With gratitude,

May 2026

PUBLISHER

Laura Sabia | laura.sabia@citylifestyle.com

PUBLICATION DIRECTOR

Emma Parente | emma.parente@citylifestyle.com

MARKET SUPPORT ASSISTANT

Lara Casiple | lara.casiple@citylifestyle.com

ACCOUNT MANAGER

Adam Vohra | adam.vohra@citylifestyle.com

CONTRIBUTING WRITERS

Leslie Kumar, Megan Schinella, Tanya Meyers

CONTRIBUTING PHOTOGRAPHERS

Brook Road Photography, ChiChi Ubiña

Corporate Team

CEO Steven Schowengerdt

President Matthew Perry

COO David Stetler

CRO Jamie Pentz

CoS Janeane Thompson

AD DESIGNER Mary Albers

LAYOUT DESIGNER Rhiannon Coffman

QUALITY CONTROL SPECIALIST Megan Cagle

Proverbs 3:5-6

inside the issue

city scene

WHERE NEIGHBORS CAN SEE AND BE SEEN

business monthly

ROUNDUP

New Business: HouseGuest

HouseGuest is a Darien-based home and pet check service created by local residents Katie and Dustin Gordon. Designed for busy homeowners and frequent travelers, HouseGuest provides reliable visits to check your home, bring in mail and packages, monitor home systems, and care for pets with walks, feeding, and photo updates. Instead of coordinating neighbors, pet sitters, and vendors while you’re away, HouseGuest gives you one trusted local point person to keep an eye on everything.

Formula X Expanding to Darien and Other Fairfield County Locations

Formula X is expanding its mobile car scratch repair service in Darien and Stamford, bringing professional-grade, rapid-response auto restoration directly to driveways and offices across key Fairfield County neighborhoods, including Springdale, Glenbrook, and Noroton. Equipped with self-contained mobile units and advanced color-match technology, the expansion ensures high-precision scratch repair, paint correction, and protective coatings are available within hours.

Coming Soon to Darien: Romanacci

Romanacci is bringing its Italian fare to Darien this fall, marking the sixth location for brothers Maurizio and Graziano Ricci. The new eatery will open in Heights Crossing, expanding the Fairfield County footprint that includes Trumbull, Westport, Norwalk, Fairfield, and Compo Beach. Known for its homey Italian-style dishes and treats, Romanacci joins the Riccis’ portfolio alongside their more formal Osteria Romana restaurants, offering residents a casual, family-friendly dining option in the heart of Darien.

MOST IMPORTANT CONVERSATION

Inside Greenwich’s on Women’s Health

160 WOMEN GATHERED FOR AN UNFILTERED, SCIENCE-BACKED DIALOGUE REDEFINING HOW MODERN WOMEN APPROACH HEALTH, LONGEVITY, AND INFORMED DECISION-MAKING TODAY

ARTICLE BY LAURA SABIA | PHOTOGRAPHY BY BROOK ROAD PHOTOGRAPHY

On a beautiful Friday morning in early March, something different unfolded in Greenwich.

It wasn’t just another wellness event. It wasn’t a panel built on trends, soundbites, or surface-level advice. Instead, it was a room filled with over 160 women who were engaged, curious, and ready for a more honest conversation about their health.

The Women’s Health Revolution, brought to us by Penny Goffman of That Penny Connect and powered by ESSE Care, delivered exactly that.

From the moment guests arrived, the energy in the room was unmistakable. There was a sense that this wasn’t just about gathering information, it was about gaining clarity. About asking better questions. About finally having access to conversations that, for too long, have been either overlooked or oversimplified.

At the center of the morning was a clear mission: to bring together leading voices in women’s health to discuss what is actually happening in women’s bodies and what can be done about it.

The result was a powerful, science-backed dialogue that challenged outdated narratives and replaced them with something far more valuable: understanding.

Throughout the day, three highly respected physicians, Dr. Karli Provost Goldstein, Dr. Alicia Robbins and Dr. Tania Elliott took the hot seat moderated by host, Penny Goffman, each offering insight grounded not only in research, but in real clinical experience. Topics ranged from hormone health and metabolism to longevity, preventative care, and the often-misunderstood realities of perimenopause and menopause.

What made the conversation so impactful was its tone.

It was direct. It was nuanced. And perhaps most importantly, it was honest.

There was no one-size-fits-all solution presented because there isn’t one. Instead, the experts emphasized a more personalized, proactive approach to care, one that reflects the complexity of women’s health and the individuality of each patient.

For many in attendance, that message alone was transformative.

Women today are navigating more information than ever before, yet often feel less certain about what actually applies to them. Social media, conflicting advice, and outdated assumptions have created a landscape that can feel overwhelming, even for the most informed.

This event cut through that noise.

Rather than simplifying the conversation, it elevated it. Offering attendees a deeper understanding of how different systems in the body interact, why symptoms often have multiple contributing factors, and how modern medicine is evolving to better support long-term health.

A major theme throughout the evening was the shift from reactive to proactive care.

Instead of waiting for symptoms to escalate, the experts emphasized early intervention, consistent monitoring, and lifestyle habits that support health over time. Strength training, nutrition, sleep, and stress management were discussed not as trends, but as foundational pillars.

At the same time, the conversation acknowledged the critical role of medical innovation.

Advancements in hormone therapy, metabolic treatments, and diagnostic tools are changing what is possible for women allowing for more targeted, effective care than ever before. For many attendees, this represented a turning point: a realization that suffering through symptoms is no longer the expectation.

It was a message that resonated deeply.

Equally impactful was the sense of community in the room.

While the information shared was powerful, the experience of being surrounded by other women and asking similar questions, navigating similar challenges, and seeking similar answers created an environment that felt both validating and energizing.

This is where events like this extend beyond education.

They create connection.

They foster confidence.

And they remind women that they are not navigating these experiences alone.

Behind the scenes, Penny played a pivotal role in bringing this vision to life. With a focus on elevated, intentional experiences, the event was not only informative, but thoughtfully curated from the caliber of speakers to the overall atmosphere.

It reflected a deeper understanding of what women are looking for today: not just information, but access. Not just answers, but guidance they can trust.

And perhaps most importantly, a space where conversations about women’s health are taken seriously.

As the day came to a close, it was clear that this was not a one-time event.

It was the beginning of something larger.

A shift in how women approach their health. A demand for better conversations, better care, and better outcomes. And a growing recognition that informed, empowered women are changing the standard not just for themselves, but for the future of healthcare.

Because when the conversation changes, everything else follows.

THE WOMEN’S HEALTH REVOLUTION

Powered by ESSE Care in Greenwich, this sold-out event brought together over 160 women and leading medical experts for an unfiltered conversation on hormones, metabolism, and longevity, signaling a powerful shift toward more informed, proactive, and personalized approaches to women’s health and wellness.

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TERESA ALASIO MD Owner & Medical Director

7 SPRING TRENDS THAT ACTUALLY MAKE SENSE FOR REAL LIFE

modeT GUIDE:

Spring dressing always feels exciting to me. It is that moment when everything starts to feel lighter, fresher, and full of possibility. Yes, the weather can still be a little unpredictable, and getting dressed during that in-between time is not always as effortless as it looks, but that is also what makes spring such a good time to rethink what you already own and bring in pieces that make your wardrobe feel new again. It is not about buying a whole new wardrobe, it is about finding what feels current, easy, and right for real life. When I shop for clients or edit closets, I am never looking at trends just because they are trends. I always want to know what actually translates into real life, what feels current without feeling forced, what works with pieces you already own, and what makes getting dressed feel more fun instead of more complicated. What I like about Spring 2026 is that the season feels expressive, but still very styleable. These are the seven trends that feel fresh and current, but still easy to wear in a way that feels personal and real.

ARTICLE BY TANYA MEYERS, FASHION STYLIST

1. STRONG COLOR, USED IN A SMART WAY

Spring 2026 is colorful, but not in a soft pastel-only way. The mood feels bolder and more personal, think tomato red, violet, and cobalt blue. There is definitely more color in the mix this season, and it is making even simple outfits feel more alive.

The modeT way:

You do not need to wear bright color head to toe. Start with one piece. A strong blouse with denim, a bright knit with neutral trousers, or a colorful flat with your basics is usually enough.

2. SHEER LAYERING

Lace layers, corset shapes, slips, and sheer pieces are all part of the conversation, but the version that works in real life is about balance, not revealing too much.

The modeT way:

A slip skirt with a simple knit, a lace-trim camisole under a blazer, a softly structured corset top with denim, or a sheer layer under something more tailored can look incredibly beautiful when styled the right way. Something delicate almost always looks better with something a little more grounded.

3. SPORTY POLISH

Sporty silhouettes are still a big part of spring, but they feel cleaner, more polished, and much easier to wear now. Easy layers, utility details, zip-front pieces, shell jackets, sleek sneakers, and practical shapes are all part of the mix, but styled in a way that feels intentional rather than too casual.

The modeT way:

This is where dressing up track pants can actually look incredibly chic. A track pant with a blazer or crisp button-down, a sporty shell with trousers, or a sleek sneaker with a fuller skirt all work beautifully. The key is to mix the sporty piece with something more refined so the overall look feels balanced and polished.

4. DIRECTIONAL SHAPES AND NEW PROPORTIONS

Spring 2026 is not only about color or texture, it is also about shape. Peplums, puffed pants, dramatic shoulders, bubble hems, fringe, and other sculptural details are part of what is making the season feel fresh.

The modeT way:

When a piece has a stronger shape, I like to keep everything around it simpler. A peplum top with straight jeans, puffed pants with a fitted tank, or a sculptural jacket with a slim trouser can look incredibly chic. Let one shape lead so the outfit feels balanced instead of busy.

5. STATEMENT SKIRTS, INCLUDING PLEATS AND MOVEMENT

Skirts are having a real moment this season, especially styles with movement, texture, pleats, or stronger proportions. It is one of the easiest ways to make an outfit feel current without trying too hard.

The modeT way:

If the skirt has volume, pleats, or movement, keep the top simple. A fitted tank, slim tee, or easy cardigan usually works best. I also love a beautiful skirt with a sneaker or flat because it keeps the look relaxed and wearable.

6. LEATHER JACKETS

A good leather jacket still earns its place every spring, but this season the shapes feel a little fresher. I especially love the slightly cropped and slouchier moto styles right now, and rich brown feels like a really nice update if you already own black. The modeT way:

Throw it over a feminine dress, wear it with jeans and a white tee, or layer it over lace to make the whole look feel a little less sweet and a little more personal.

7. SOFT ELEGANCE, WITH ROOM FOR PERSONALITY

One of the things I like most about Spring 2026 is that it does not feel too rigid. There is a softer, more fluid kind of polish this season, and that is a big part of why the trends feel so wearable. The modeT way:

A fluid trouser with a tank, a soft blazer over denim, or an easy dress with a beautiful flat hits that sweet spot. Polished, but not stiff. Put together, but still comfortable.

What I like most about this season is that you do not have to pick just one trend and fully commit to it. The best outfits usually come from mixing a few elements in a way that feels right for you, a strong color with denim, a statement skirt with a sporty jacket, lace with leather, or a directional shape with something simple. And sometimes it is the finishing pieces that really make the look, oversized sunglasses, a great silk scarf, a polished belt, or a statement earring can completely change the feel of an outfit.

That is always the modeT way: not chasing every trend, but choosing the pieces that make you feel your best and fit naturally into your life.

And do not forget to check your local boutiques when the new collections start coming in. That is often where you find pieces that feel special and wearable, not just trend-driven for the sake of it. Some of my go-tos are I Am More in Scarsdale, Pologeorgis and Nobelle in Greenwich, and Saujette in Larchmont, with Darien coming soon.

Happy Spring!

ARTICLE BY LAURA SABIA

THE SUPPORT

Every Mother NEEDS

“THE EASIEST WAY TO THINK OF US IS AS A WEDDING PLANNER BUT FOR BABIES, GUIDING FAMILIES THROUGH PREGNANCY WITH CLARITY, CONFIDENCE, AND TRULY PERSONALIZED SUPPORT.”

For many women, pregnancy begins with excitement and quickly turns into overwhelm. Between endless product lists, conflicting advice, and the pressure to “get everything right,” preparing for a baby can feel less like a joyful milestone and more like navigating uncharted waters.

For Danielle Beale and Chelsea Zlotnick, that realization wasn’t theoretical, it was personal.

A MODERN MATERNITY CONCIERGE HELPING FAMILIES NAVIGATE PREGNANCY AND EARLY PARENTHOOD WITH CLARITY AND CONFIDENCE

The two met on a tennis court while Chelsea was pregnant with her first child. What started as casual conversation soon turned into a shared question they couldn’t ignore: why is there so much support for planning a wedding, but almost none for planning a baby?

That question became the foundation of Vela Motherhood, a modern maternity concierge designed to guide families through pregnancy and early parenthood with clarity, confidence, and personalized support. (“Vela” means to sail or navigate—a fitting name for such a transformative journey.)

“The easiest way to think of us is as a wedding planner but for babies,” they explain.

Vela helps eliminate the decision fatigue that so often defines this season of life. From registry building and postpartum preparation to fertility guidance and assembling a trusted care team, their approach is deeply personalized. Every recommendation is tailored to a family’s lifestyle, down to their home layout, daily routines, and support system ensuring each decision feels aligned, not overwhelming.

While many clients initially come for registry support, what they gain is far more impactful: clarity, confidence, and a sense of calm during a time that can otherwise feel chaotic.

That impact is perhaps best illustrated through one client experience.

While preparing for her first baby, one mother was also managing a cross-country move and placing her own mother into memory care. “She told us she didn’t have the mental space to think about anything else,” they recall. After building her registry and creating a clear plan, the client shared that it felt like a physical weight had been lifted from her shoulders.

“That’s when it really clicked,” they say. “This isn’t just about baby planning, it’s about giving people peace of mind.”

Rooted locally, Vela has built a trusted network of vetted providers across Fairfield and Westchester counties, allowing them to connect clients with high-quality professionals they know and stand behind. Their work reflects a broader shift: parents today have more information than ever, but less clarity. Vela bridges that gap with thoughtful guidance and trusted support.

As they look ahead, Danielle and Chelsea are focused on growing intentionally, expanding their services while maintaining the personalized experience that defines their work.

Because when families feel supported, everything changes.

ARTICLE BY MEGAN SCHINELLA

Local Experiences

THE BEST PLACES AND THINGS TO DO IN OUR AREA.

1. Kiin Sauna | brings the restorative power of a handcrafted wood-burning sauna and cold plunge. With a focus on nature, connection, intentional living, and reconnecting with friends, each other, and the natural world. Fairfield CT.

2. Clubhouse | offers incredible food and fun activities, including two private karaoke rooms, golf, darts, virtual sports, along with a rooftop deck. Check them out for your next girls night! Westport, CT.

3. Forever Young Head Spa | head spa for 2, specializing in scalp health and head spa treatments, including scalp analysis, massage, and facials. Self-care quality time with a friend. This is your sign to indulge in relaxation. Stamford, CT.

4. Felice Restaurant | new and inspired by the Tuscan countryside, family-owned neighborhood restaurant rooted in warmth and authenticity. Rustic Italian classics, an Italian-driven wine list, and genuine hospitality come together in a vibrant, welcoming setting. Westport, CT.

5. La Beaute Artistry | time to grab the girls and get your nails done together. Penny and her team are known for their exceptional nail artistry. Westport, CT.

Megan Schinella

Grab your gal pals and plan a relaxing or upscale day, weekend, or Girls night out with these local experiences!

ARTICLE BY KALI KASORZYK

PHOTOGRAPHY PROVIDED

BECKY HILLYARD

From Side Hustle to Style Empire

The power of taste, trust, and the courage to “just start.”

She didn’t have a business plan, a media budget, or even a name anyone could pronounce. What Becky Hillyard had was taste, a young family, and the instinct to just start. Today, her lifestyle brand Cella Jane commands an audience the size of Vogue’s, she’s nine collections strong with Splendid, and she’s built it all while raising three kids — refusing to sacrifice one for the other. In an exclusive conversation for the Share the Lifestyle podcast, Becky shares what it really takes to build a brand, a career, and a life you love. Read the highlights below, then scan the QR code for the full conversation.

Q: WHEN DID YOU KNOW CELLA JANE WAS MORE THAN A HOBBY?

A: Two moments. Women started emailing me saying they bought something I recommended and felt amazing — asking me to help them find a dress for a wedding. That felt incredible. Then I looked at my affiliate numbers for one month and realized I could cover our mortgage. I thought, I can actually do this. I never set out to build a business. I started it because I genuinely loved it.

Q: WHAT WAS THE BIGGEST RISK YOU EVER TOOK WITH THE BRAND?

A: Designing my own collection. It’s easy to point at items on a website and say I love these. But to create something from scratch, put your name on it, and wait to see if people connect with it — that’s terrifying. I had an incredible partner in Splendid, and women loved the pieces. It was the biggest risk and the biggest accomplishment.

Q: HOW HAS INFLUENCER MARKETING CHANGED SINCE YOU STARTED?

A: When I started, brands didn’t know whether to take it seriously. Now it’s a legitimate line item in their marketing budgets — sometimes bigger than TV. Because what we’ve built is trust. People trust a real recommendation from someone they follow far more than a commercial. There’s no question about it now.

Q: YOU’RE A MOM OF THREE RUNNING A FULL BRAND. WHAT DOES YOUR DAY ACTUALLY LOOK LIKE?

A: I try to get up at five and not hit snooze — that first hour before the house wakes up is the most productive, most peaceful hour of my day. Then it’s all hands on deck with the kids and school drop-off. After that I work — planning content, connecting with my team, editing. After pickup, the day shifts completely and it’s all about them. I’ve learned to protect both halves fiercely, because both matter.

Q: WHAT WOULD YOU TELL SOMEONE WHO WANTS TO BUILD SOMETHING OF THEIR OWN BUT KEEPS WAITING?

A: Don’t wait. Don’t wait for the perfect camera, the right strategy, or enough followers. We find every excuse to stay comfortable. Just start, be consistent, and be authentically yourself. The right people will find you — and they’ll stay.

This conversation is just the beginning. Becky goes deeper on the risks that almost stopped her, the design process behind her latest Splendid collection, and what she’d tell her 2012 self today. Scan the QR code for the full, exclusive City Lifestyle interview on the Share the Lifestyle Podcast.

“Trust is the only metric that actually compounds.”

— Becky Hillyard

The Community Fund of Darien - Designed to Dine

Woodway Country Club, Darien CT | 2:00 PM

Designed to Dine returns bigger and better with two signature events in one day, celebrating The Community Fund of Darien's 75th Anniversary and nearly $30 million granted since 1951 to local nonprofits supporting the basic needs of our neighbors in Stamford, Norwalk, and Darien.

MAY 7TH

9th Annual Lecture & Luncheon with Featured Speaker Kathryn Herman

New Canaan Country Club | 11:30 AM

The New Canaan Nature Center invites you to join them for their 9th Annual Lecture & Luncheon! With Kathryn Herman as the featured speaker, this luncheon is more than a gathering—it’s an opportunity to come together as a community and support the New Canaan Nature Center!

MAY 10TH

Mother’s Day at the New Canaan Farmers Market

244 Elm Street New Canaan, CT | 10:00 AM

Celebrate Mother’s Day at the New Canaan Farmers Market with a charming morning filled with fresh flavors and local finds! Stroll through the market to discover seasonal produce, flowers, baked goods, and artisan treats from Connecticut vendors. With live music and a community atmosphere, it’s the perfect spot to pick up a  gift or enjoy a relaxed outing with mom.

MAY 17TH

Cars and Coffee Darien

Goodwives Shopping Center

7:00 AM

Mark your calendars! Join Cars and Coffee Darien for their May event, when they will be featuring the cars of England and the United Kingdom. As usual, all make and models are welcome! Come on down and enjoy a diverse display of classic, sports, and exotic cars, bikes, and trucks.

MAY 29TH

2026 Annual Gala

Celebrate New Canaan

New Canaan Museum & Historical Society | 6:30 PM

Join the New Canaan Museum & Historical Society under the moonlight for their annual gala and fundraiser! Dance to the music of Fake ID Band and dine on delicious food prepared by Diane Browne Catering. This year longtime Board Governor and current president Tom Monahan, and his wife Cynthia, will be honored for their years of dedication to the Museum.

MAY 31ST

New Canaan Dog Days

New Canaan Nature Center

11:00 AM

Get ready for a tail-wagging good time! Hosted by Pet Pantry Warehouse, New Canaan Dog Days is a beloved community event that is free and open to the public,  and it all benefits AdoptA-Dog and the Nature Center. This annual celebration brings together pet lovers, families, and furry friends for a great cause.

Want to be featured?

ASK LESLIE!

Welcome to the May Ask Leslie!

In February, Ask Leslie guests gathered at N. West Gallery in New Canaan to celebrate the official launch of the column. It was one of those evenings that will stick with me and remind me why starting something new feels so exciting.

During my remarks, I shared a little about how Ask Leslie began. I started this column because I wanted to do something different, something creative, something fun, and something that felt very me. I’ve always loved writing, and have been fascinated by advice columns and the subtle role etiquette can sometimes play in our everyday lives. Not to mention, I have a thing for dishing out advice even if nobody asked for it…

One of my favorite details of the party was a pink telephone, stationed in the gallery on a pedestal like a piece of art, where guests could record their own Ask Leslie questions. The questions in this issue came straight from that phone!

The party would not have been possible without wonderful partners who helped bring it to life. Thank you to Owl’s Brew, who debuted their new Spiked Pop beverages at the event, Palmers Darien for the delicious catering, and The Vintage Horse — Jennifer Milano’s fabulous mobile bar — for the on-brand specialty cocktails. I’m also grateful to Junction Studio, owned by my dear friend Laura DeRemer, for planning and

setting up the evening (love you!), RooNee for the beautiful florals and Nabil West for generously hosting us in his New Canaan gallery space and of course, Darien New Canaan Lifestyle, the magazine that gave Ask Leslie a home. And! I’m thrilled to share that Ask Leslie is now also appearing in Upper Westchester Lifestyle, bringing even more readers and questions into the conversation!

Thank you so much to all these companies for your support and making the Ask Leslie launch party an event to remember.

Hope you enjoy this month’s column. As always, thanks for reading!

xx Leslie

How should I think about aging? I recently turned 50 and am finding it difficult to wrap my head around this milestone.

Dear Chapter 50,

First of all, congratulations! Turning 50 is indeed a milestone, and milestones deserve to be celebrated. I think people spend time worrying about how quickly they’re getting older instead of appreciating how great it is to be exactly the age they are right now. You’re 50, not old. Your 20-year-old self may have thought 50 sounded ancient, but when you’re 70, how do you think you’ll feel about 50? My guess is you’ll think, Wow…50 was pretty great. This may simply be a matter of shifting your perspective. We do this with other stages of life too. When your kids are toddlers, you can’t wait for them to finally start kindergarten. When you’re on a week-long vacation, by day five you’re already feeling sad that it’s almost over (guilty!). Instead of simply enjoying where we are, we tend to focus on what’s coming next or what we’re about to lose.

For the record, I’m five years behind you and I’m already brainstorming my 50th birthday bash (no judgment, please). Planning the celebration makes the number feel far less important, because that’s really all it is, a number. Until someone discovers the fountain of youth, time is always undefeated. Move your body, eat well, travel, celebrate milestones (!!), love people, and let yourself be loved.

As Pablo Picasso once said, “It takes a long time to become young.”

And honestly, 50 is pretty prime. You’re established, experienced, and hopefully savvy enough to enjoy life in a way your younger self couldn’t.

Not a bad place to be.

— Leslie

I’m a single female in my 20’s living in Fairfield County. Where do you meet people in CT when most people are older, established and have families? Where do other young singles hang out?

Dear Single & Ready to Mingle,

While I have no direct experience with today’s dating scene, I do know it can be challenging to meet people these days.

I’m definitely not well equipped to answer this question and I owe it to you and all Ask Leslie readers to give my best advice, so I tapped Jill Dunn, a dating expert and founder of Jillin’ It to help out here. Here’s what she had to say:

You’re not imagining it . C ertain parts of Fairfield Count y can feel like they jump quickly from college towns to family life. But plenty of young professionals are here; they’re just not always gathering in obvious “singles” environments.

In my experience as a professional matchmaker, the best place to meet single people , at any age really, is less about traditional “dating scenes” and more about putting yourself in social environments where interesting, active , likeminded people naturally spend time. Fitness communities, recreational sports leagues, volunteer organizations, alumni events, and social interest groups can all be great ways to meet people organically because you’re already starting with something in common.

Another reality of modern dating is that introductions still matter. Because the community is smaller than a big city, people often meet through friends, events, and curated networks rather than just randomly bumping into someone at a bar.

The key is to stay socially engaged, keep expanding your circles, say "yes" more than you say "no" and remember that great connections often happen through community and personal connection rather than chance encounters.

I hope you find this helpful and hope you find what you’re looking for...or it finds you.

— Leslie

Want to submit a question to Ask Leslie? Email darien@ citylifestyle.com or DM Leslie directly on Instagram (and follow along!): ask_leslie_official. All submissions are confidential and anonymous.