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. Certain parts of Fairfield County 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, like-minded 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.