Welcome back to Ask Leslie! Your guide to life’s everyday dilemmas.
I love where Ask Leslie lives in this issue — somewhere between etiquette and emotion. The questions we think are about fashion, calendars, or plane tickets are really about something deeper: connection, belonging and guilt.
Thank you for reading.
xx
Leslie
When you admire a standout piece on someone, is it acceptable to ask for details — or does this cross a quiet social boundary? And does the fact that they’re a complete stranger change the rules?
I love this question. Because it’s really about style, yes — but it’s also about connection.
Before I answer, let me tell you how I found my all-time favorite coat..this might not be interesting, but I’ll share it anyways.
It was a chilly October afternoon at Bloomingdale’s 59th Street. I was wandering through the jewelry department when a woman walked by in the most beautiful coat — color-blocked wool, straight cut, high Nehru collar. Chic. Timeless. I needed it.
I complimented her first (of course), and asked where she found it. The moment I had internet access, I hit the buy button on JCrew.com. That was twelve years ago and I still wear it every season. And I still get compliments every single time.
All of this to say: when you genuinely admire something, say so!
A sincere compliment can absolutely make someone’s day — sometimes even their week. And! You also get the bonus of intel on your new favorite piece. It’s a win-win.
Now, does it cross a social boundary? Not if it’s done thoughtfully.
With a friend, just be yourself. With a stranger, lead with friendliness and a smile:
“Hi — I hope you don’t mind me saying, but your scarf is stunning and I feel like I need one. Would you mind sharing where you found it?”
The fact that they’re a person you’ve just met doesn’t change the “rules” — it just calls for a bit more social awareness. Most people are delighted to share when you’re being genuine.
Style is personal, but sharing the details? That’s usually part of the fun! (Unless you’re asking for my babysitter’s contact. That’s classified.)
— Leslie
My family and friends who have more flexibility in their lifestyles and jobs will schedule extravagant trips. How do I manage the relationship when I cannot attend these trips? I feel like I'm always turning them down. How do I come up with other ways to fuel the relationship?
You don’t have to travel far or spend crazy to create rich memories. Some of the most meaningful, luxurious-feeling experiences don’t require a passport… just a free weekend and fuel in the tank.
We are surrounded by incredible places and moments right here at home. “Extravagant” doesn’t need to be about distance and dollars — it can be about how you choose to experience it.
Here are a few of my favorite little indulgence destinations, all within an hour or so of Fairfield County. These are fabulous options to spend the day, or day and night if budget allows.
The St. Regis New York - New York, NY / @stregisnewyork
Bedford Post Inn - Bedford, NY / @bedfordpostinn
The Mayflower Inn & Spa - Washington, CT / @mayflowerauberge
The J House - Greenwich, CT / @thejhousegreenwich
— Leslie
I’m an only child of divorced parents. I live on the East Coast near my mom, who’s single, and I see her often. My dad lives in Texas near his stepchildren and grandchildren, and he frequently tells me I don’t visit enough. The truth is, I don’t always want to — so I tend to avoid the conversation. How can I find a healthier balance with both parents without feeling guilty or like I’m constantly disappointing someone?
Oh, this is layered.
Being an only child of divorced parents can feel like its own emotional job, I’m sure. You’re constantly weighing: Who needs me more? Who am I disappointing this time? Who feels left out?
And I understand why you avoid the conversation, but avoidance isn’t a long-term strategy.
Try stepping into his perspective for a sec. You’re his only child. He may very well be thinking, I just want time with her while I still can. Time moves quickly.
So… at some point, you probably have to bite the bullet and go see your dad. The relationship requires presence, even if it’s not as effortless (or as fun) as the one with your mom (believe me, I get it!).
Not wanting to hop on a plane constantly doesn’t make you a bad daughter. It makes you totally human.
Consider committing to and scheduling your visits with your dad ahead of time. When it’s clear and concrete, there’s less ambiguity — and fewer guilt-filled, uncomfortable conversations to avoid.
– 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.
Extravagant doesn’t need to be about distance and dollars — it can be about how you choose to experience it.