It took you three months to ask her out on a date. And you were sweating bullets each and every moment.

But you did it (congratulations btw), and now you’re sweating bullets all over again, thinking, dinner and a movie? Too cliché. A stroll in the park? It’s too cold for that. The local hole in the wall? Not nearly special enough.

And that's the thing—it needs to be super special. Maybe like a diminutive room in a tower, or a riverside dome catered to by an award-winning winery, or a sultry speakeasy hidden in the depths of a Chinese bakery.

Yeah, you're welcome.

The Robey

The Robey, @AdrianGaut courtesy of GRUPO HABITA

The Grotto at The Robey

When Wicker Park/Bucktown’s iconic Coyote Building was reinvented as The Robey hotel, the 13th floor outdoor/indoor cocktail lounge now known as The Up Room was nothing more than a desolate rooftop accessed by a flight of stairs. In the corner stood a tower, and within it a recess, used by engineers to perch a precarious ladder in order to light the lantern at its very tip.

The lantern shines on to this day. But post-renovation, the tower has another reason to be.

The Coyote’s "Grotto" was built out and embellished with chandeliers, cushy benches and heaters, an amber glow emanating from its open entry every evening. It’s a natural extension of The Up Room, with its amazing views stretching across the city.

Although the Grotto can occupy 10-15 people, turn the dial up on the romance-o-meter by booking the space for just the two of you (minimum food and beverage package applies). And yes, more than a few people have heard the words, “Will you marry me?” uttered in this sultry, intimate space.

Oh, and just so you know, The Robey was named one of 2017’s “Best New Hotels in the World” by Travel + Leisure. Your date will love that you know that.

Visit The Robey or call (872) 315-3046 for more info.

River Domes - City WineryPhotography by Paul Crisanti, courtesy of City Winery

River Domes, City Winery at Riverwalk

Imagine savoring a bottle of award-winning wine, looking out onto the cool waters, and drinking in the city’s glittering skyline from an intimate, inviting dome situated along the Chicago Riverwalk. Rather than imagine it, why not just book it.

Chicago favorite City Winery is offering its guests access to six heated River Domes—a unique experience that allows you to enjoy the outdoors without freezing your…well, getting cold. Each dome comes complete with a Bluetooth speaker and is exclusively outfitted by Wayfair Professional. 

Reservations already are being taken, with availability between March 20 through May 6, from 11am - 9pm daily. Each reservation lasts two-and-a-half hours and costs $85 per person, which includes a $60 food and beverage minimum spend. You’ll enjoy full service from City Winery’s spring Riverwalk menu, which features the most popular starters, salads and sandwiches from the restaurant’s distinctive small-plate, sharing-and-pairing concept, plus items unique to the Riverwalk such as house-made tap wines, beer and cocktails.

Oh, and by the way, City Winery (1200 W Randolph) has produced dozens of in-house wines sourced from vineyards in California, Oregon, Washington, Argentina and Chile, including a Wine Enthusiast 90-point 2012 Bien Nacido Vineyard Reserve pinot noir. It was also recognized by Wine Spectator with a 2014, 2015 and 2016 Best of Award of Excellence “for having one of the most outstanding restaurant wine lists in the world.” 

City Winery at the Riverwalk is located on the south bank of the Chicago River between Dearborn and State Streets, 11 W Riverwalk South. Reservations can be made online through OpenTable.

The Ladies Room - Fat RiceCourtesy of Fat Rice

The Ladies’ Room, Fat Rice

For all the feels of a clandestine, uber romantic meeting, head to this tiny, reservations-only Chinese speakeasy, so well hidden you have to enter through a curtain near the restrooms and around the pie racks at Fat Rice Bakery.

Chicago Magazine named The Ladies’ Room one of “Chicago’s 50 Best Bars” for a reason. Subdued vermillion lighting, vintage pin-up art and 1920s Chinese decorations draw their inspiration from Macau’s red light district, making the space irrepressibly fun, exotic and exclusive. You’ll also find a board game at every table, reinforcing the Chinese gambling hall vibe.

There’s a small snacking menu, but the cocktail menu is the showstopper. The classics are reimagined with such tantalizing names as A Dangerous Summer (Neissen Agricole, Feni, Rose Cordial, Grapefruit, Lime) and John Was The Teeth (Calvados, Yellow Chartreuse, High West Double Rye, Great King Street Glasgow Scotch Rinse). “New Mad Style” cocktails take your wild imaginings to a whole new level, with drinks like Surfer On Acid On Acid (Blended Scotch, Braulio Amaro, Yellow Chartreuse, Pineapple, Avocado Leaf Tincture, Salted Coconut Foam) and Onu You Didn’t (Onu Tuica Romanesca, Gin, Plum Shrub, Umeboshi Vinegar, Visinata). Or you can go large-format, each grabbing a straw, staring into each other’s eyes, and sharing the likes of Hot Tea (Onu Tuica Romanesca, Letherbee Gin, Rare Tea Cellar’s Freak of Nature Oolong) and Burning Bird (Plantation Pineapple Rum, Aperol, Campari, Palm Sugar, CH Amaro, Calamansi, Pineapple), which actually serves four, but who’s counting?

The Ladies’ Room is located at 2957 W Diversey Ave in happening Logan Square. Want to know more? Visit online or call (773) 661-9170.