If We Had the Day...
Or an afternoon. Or an evening. Or a weekend.
Some of my favorite memories have nothing to do with where I was. They have everything to do with who I shared the experience with.
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A long lunch that turns into cocktails. Wandering through a museum with nowhere else to be. Sitting in a beautiful hotel suite watching the city change from day to night. Finding a restaurant we’ll both talk about months later. Even something as simple as walking through a neighborhood neither of us knows very well.
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I think that’s what draws me to this life.
Not checking destinations off a list, but sharing experiences that make life feel a little richer, a little more beautiful, and a little more memorable than it did the day before.
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Sometimes we make reservations a week in advance. Other times we unexpectedly discover a place and decide to stay longer than planned. I like leaving room for curiosity and spontaneity. For the possibility that the best part of our day hasn’t happened yet.
My goal isn’t just check off all the beautiful hotels, incredible restaurants, or first class experiences... although I’ll never say no to any of those. It’s having the time to actually enjoy them. To linger over dessert. To order another cocktail because the conversation is too good to end. To wander without needing a destination. To laugh until we forget what time it is.
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The ideas below aren’t rules or itineraries. They’re examples of the experiences I enjoy most. Perhaps they'll inspire an idea of our own.
A First Taste
90 Minutes
It’s just enough time to satisfy your curiosity… and often enough to leave us both wanting another date. Sometimes all it takes is enough time for introductions to turn into easy conversation, for the nerves to disappear, and for curiosity to become comfort. I’ve always believed chemistry isn’t something you force, it’s something you feel. This is where we begin.
The Slow Burn
Three Hours
There’s no need to rush through conversation or glance at the clock every few minutes. We have time to simply let the afternoon or evening find its own rhythm. Sometimes it’s the conversations I remember most. Sometimes it’s laughing over something completely ridiculous. Sometimes it’s realizing we forgot about our phones hours ago.
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It’s long enough to become comfortable with one another, but just short enough that you’ll probably find yourself wishing for one more hour. And the best part? Three hours often feels like it passed in thirty minutes when you’re with the right company.
The Classic Date
Four to Six Hours
Long enough for lunch or dinner to become much more than just a reservation. Say we start with a bite at our hotel bar before walking to find dessert someplace else. A dinner ends with a walk because the evening is too nice to waste inside. A gallery, live music, a rooftop, a hidden speakeasy, or discovering somewhere new together.
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Or perhaps we keep it beautifully simple. Great food. Easy conversation. A bottle of wine. No agenda beyond enjoying each other’s company. My favorite memories begin exactly this way.
The Adventure
Up to Eight Hours
By now, we’ve stopped asking “what should we do?” and started asking “what sounds fun?” That matters more than it sounds like it should, it’s the difference between filling time and actually curating a day together.
Sometimes the best adventures aren’t planned, they’re discovered. Maybe it’s a museum we didn’t expect to spend two hours in. A helicopter tour, a show, an afternoon spent shopping with no real agenda. A couples massage at the hotel spa, followed by drifting back to the suite because it suddenly feels like the better plan.
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I love experiences that resist being recreated exactly the same way twice. Give me eight hours and I promise you: the itinerary will matter far less than what we’re both like by the end of it.
The Overnight
Some dates start well and only get better from there...
This is where the version of me you haven’t met yet tends to show up. A little less "on", a little more myself. The conversation that wanders somewhere unplanned around midnight. Falling asleep still talking. Waking up to the version of each other that doesn’t perform, we just get to be.
A suite just for us. Room service, music low, no particular plan for the morning. We can talk until 2am, sleep in, and see who we are before either of us has had coffee. That’s not a small thing. And it's one reason why this is my personal favorite.
Twenty-Four Hours
A day together has its own arc: morning, afternoon, evening, and the version of me that meets you at each one is a little different.
By midday, the small talk is long gone. By evening, we’ve probably changed plans twice because something better came up, and neither of us minded. This is where I stop being someone you’re getting to know and start being someone you already do.
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There’s time to linger over breakfast, revisit somewhere we loved, or discover something new entirely. The day stops feeling scheduled and starts feeling like ours. Those are the experiences I still think about months later... because of how much of each other we got to see.
Seventy-Two Hours
By day three, this stops being a date and starts being something closer to our own little world, brief... but deeply enjoyed.
Day one has its own energy: a little formal, a little electric. By day two, that’s replaced by ease. By day three, we’ve built inside jokes, routines, a shorthand that didn’t exist 48 hours earlier. That’s not something any shorter experience can offer, no matter how spectacular it is... it requires time to exist at all.
Perhaps we’re exploring a new city, or returning to one we’ve both loved. Long dinners, lazy mornings, the kind of familiarity that only comes from uninterrupted time. Three days lets life stop feeling scheduled. It just happens. Those are the stories that stay with us for years.
Bespoke Experiences
Not every memorable experience fits neatly into a category. Sometimes there’s a destination you’ve always wanted someone to share with you. A special occasion worth celebrating. An evening you’ve imagined but haven’t quite known how to create.
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I enjoy thoughtful planning as much as spontaneity, and I’d be delighted to help design something that feels personal to us both. The most memorable experiences are rarely the ones anyone could have planned in advance. They’re the ones that couldn’t have happened with anyone else.
A Few Things I Love
I have a soft spot for hotel lounges where beauty, atmosphere and desire naturally converge. I’ll almost never say no to architecture, an interesting dining experience, art museums, rooftops with a view, or discovering a neighborhood neither of us has explored before. I love environments that invite us to slow down rather than rush through dinner.
Favorite Chicago Spots
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Tre Dita
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Oriole
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Momotaro
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Adalina Prime
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Asador Bastian
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The Bar at The Peninsula
A Few Things Still On My List
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Glamping at The Gwen
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A helicopter tour over Chicago
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A private sail at sunset
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A concert at Ravinia
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A weekend at a Winery
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A fall trip to Paris or New England
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A beautiful suite just because the view was too good to pass up
The most amazing days I’ve ever had began with a simple conversation and no particular expectations. If something here resonates with you, I’d love to hear what kind of day you’ve been imagining.
Let's Start Something Special
Now that you've had a chance to read about me and peruse my site, you’re ready to take the next step... reach out to me.
I’m confident that with a little bit of effort, you’ll find I’m the kind of woman who knows exactly how to make you feel like the best version of yourself.
After all, the sweetest things often begin with a simple Hello...
I eagerly await yours,
Chase