Chicago is full of indulgent little pleasures—and while I’ve had the joy of exploring a few, there are still so many places I’ve been dreaming of experiencing. Places I haven’t quite tasted yet… but fantasize about often.

If you’ve ever wanted to treat me to something unforgettable, here’s a little hint: I love new experiences, especially when they involve good food, fine wine, and even better company. These are a few of the Chicago restaurants still on my “someday soon” list—and maybe, just maybe, we’ll try one together.

Because men are visual creatures, I’ll share a photo of a dish that attracted me to these restaurants in the first place. Along with a description of the dish; let’s be honest, most of this food looks like art, can’t quite tell what it is but we’ll figure it out together.

🍽️ Boka

Everyone talks about Boka like it’s the kind of place where sparks naturally fly—cozy, romantic, with food that’s almost too pretty to eat. I haven’t been yet, but it’s on the top of my list. I imagine slipping into something elegant, taking your arm, and letting the evening feel like a slow dance of flavors and flirtation.

Photo Credit: Instagram.com/bokachicago

“Grilled Hokkaido scallops with green garlic, strawberry and buckwheat” If you’ve already read my bio, you already know that I’m a seafood lover. Who would have thought to pair scallops with strawberries? Not me.

🎨 Esmé

Esmé has this artistic, thoughtful reputation that I can’t help but be drawn to. I’ve never been, but it feels like the kind of place that celebrates the senses—perfect for someone like me who craves beauty, taste, and connection all in one experience. Maybe we could discover it together?

Photo Credit: Instagram.com/esme_chicago

“Grilled Rouget” paired with a nutty sauce “drizzled with blood orange and persimmon preserves” topped off with pine nuts. Call it a craving… I just can’t keep my hands off a nice pair of nuts.

🍺 Moody Tongue

I’ve heard Moody Tongue is known for their incredible beer and unforgettable tasting menu… but I’ve only admired it from afar. I’d love to go with someone who enjoys pairings that surprise you—and who doesn’t mind taking their time with a woman who appreciates every little detail.

Photo Credit: Instagram.com/moodytongue

Grilled octopus, a classic. Described as “Spanish octopus with confit eggplant, apple chutney, Greek yogurt and harissa.” Surprisingly, I have never tasted eggplant but I love everything else mentioned. I imagine this dish will be delicious.

🌹 Elske

Elske has been calling my name for a while now, and I’m just waiting for the perfect evening (and the perfect dinner date) to finally answer. I scroll through their menu or spot one of their artful dishes online, I find myself daydreaming. Delicate Nordic-inspired plates, candlelit ambiance, and that cozy-chic patio? Yes, please. It feels like the kind of place where time slows down and every bite feels intimate.

Photo Credit: Instagram.com/elskeresturant

“Mafaldine with braised escargot, artichoke, hazelnut, and chervil.” This… is pasta?! No way. I must try this.

🌿 Smyth

There’s something mysterious about Smyth. Maybe it’s the way people talk about the courses like they’re unfolding a story. I haven’t had the pleasure yet, but it’s definitely the kind of place I’d love to get lost in—with someone who enjoys long dinners, soft touches, and good wine poured slowly.

Photo Credit: Instagram.com/smythchicago

“Maine lobster poached in dried chili butter, glazed with fermented melon & gooseberry honey.” There’s just something so irresistible about tender lobster dripping in warm, silky flavored butter… it’s pure indulgence on a plate. Just the thought makes my mouth water.

🍣 Omakase Yume

I’m such a sucker for an intimate sushi experience, and Omakase Yume seems like the perfect kind of night: quiet, intentional, and full of delicate little surprises. I haven’t been, but I imagine being seated close together, sharing glances between courses, letting the energy stay soft and suggestive all night long.

Photo Credit: Instagram.com/omakaseyume

Uni… Caviar Royal… Ikura… Kegani… come on… this is literally everything! Delicious, yummy, yes! They have a cheesecake for dessert that I would love to get my tongue on.

🌶️ Topolobampo

Bold, spicy, and full of flavor—Topolobampo sounds like my kind of place. I haven’t had the pleasure yet, but I’d love to see what all the heat is about. Maybe a mezcal cocktail, a little laughter over shared bites… and a bit of heat that carries on long after dessert. By the way, is this place a market or a restaurant? Or both?

Photo Credit: Instagram.com/topolobampo

“25-layer chocolate mousse-crepe cake, dark chocolate sauce, whipped cream with cocoa nibs, hibiscus-poached Klug Farm cherries.” I have a soft spot for chocolate cake—decadent, fudgy, and dangerously delicious. It’s my kind of guilty pleasure.

Let’s Try Something New… Together

I believe in firsts. First glances, first touches, first tastes of something unforgettable. If you’re the kind of man who enjoys showing a woman a new experience, then I’m already intrigued.

Let’s make a reservation. Let’s linger. Let’s turn a “someday” into something real, rich, and deliciously ours.

Because I don’t just want to be taken out—I want to be taken somewhere I’ve never been.

xoxo,

A Taste I’m Still Craving: Chicago Restaurants I’m Dying to Try (Michelin Star Edition 🌟)