Dear Westchester Date Night
Dear Westchester Date Night,
My wife and I want to have more regular date nights, but between work and kids, we’re just too exhausted to plan anything. How do we make this happen without it becoming another to-do on our list?
— Tired in Tarrytown
Dear Tired in Tarrytown,
Here’s the secret: simplify. You don’t have to reinvent the wheel every week—just commit to carving out time for you two. Look for spots with built-in ambiance so you don’t have to work too hard: think cozy wine bars or chic restaurants with live music. To make it even easier, bookmark a few go-to places now so you’re not scrambling at the last minute. And if you're too tired to go out? Bring the fun home—order takeout from a trendy spot, light some candles, and queue up a rom-com. The key is consistency, not complexity—small, regular moments together can do wonders.
-----------------------------------------------------------------------------------
Dear Westchester Date Night,
I keep trying to plan a girls’ night out, but my friends are always flaking. They’re busy with their partners, kids, or work. How do I get my crew together without pulling teeth?
— Frustrated in Scarsdale
Dear Frustrated in Scarsdale,
Group texts can feel like herding cats, so take the lead with a bold move: lock in the plans yourself. Choose a date, pick a fabulous venue—maybe a lively tapas spot or a karaoke bar—and send an invite with “RSVP by X date!” Instead of endless back-and-forths, give them the option to say yes or no. Also, remind them this is about decompressing and reconnecting. Pro tip: Pick a venue offering happy hour or late-night vibes so even the busiest friends can pop in for a bit. Consistency is key—once they see how fun these nights are, it’ll be easier to rally the troops next time.
-----------------------------------------------------------------------------------
Dear Westchester Date Night,
My husband and I have been married for 10 years, and date nights have become… well, a bit of a chore. We love each other, but it feels like we’re doing the same thing every time. How can we make our nights out exciting again?
— Bored in Briarcliff
Dear Bored in Briarcliff,
First, let’s retire the “same old, same old.” Instead of heading to your go-to spots, think outside the box: try a paint-and-sip class, a speakeasy-style cocktail bar, or even a comedy night. Westchester has incredible spots that scream adventure—hello, sunset kayaking or a rooftop wine tasting! The goal is to create moments that feel fresh, not routine. And here’s a twist: let your husband plan one date, and you plan the next, without revealing a thing in advance. The element of surprise keeps things playful and exciting!
