The special-occasion date

Celebrate those very big-deal nights with these very big-deal dates.

You’re going to propose…
You found the girl of your dreams, you saved up, you bought the ring—it’s time to close the deal. Advance warning: This is the one night of your life that being over-the-top cheesy is a very good thing. Start by having her meet you at the Ledge at the Willis Tower (233 S Wacker Dr), à la An Affair to Remember …but in Chicago. After admiring your beautiful city via the glass cube dangling 1,353 feet above the street, bring her back down to earth by walking hand-in-hand over to theWit (201 N State St, 312-467-0200). She’ll think you’re headed up to ROOF for a cocktail—but instead press “4” in the elevator and whisk her into just-opened Screen, an intimate screening room that hosts private viewings ($500 for two hours). Because you’re smooth and thoughtful, you already dropped off a DVD with dozens of photos of the two of you set to Eric Clapton’s “Wonderful Tonight.” (Too cheesy? Fine, wuss, just pick a romantic flick she loves.) You also pre-ordered bubbly and her favorite foods off the menu from theWit’s State & Lake or cibo matto. Get comfy in the cushy, reclinable chairs and watch your memories unfold. Okay, now she’s perfectly primed. Pull out the ring, tell her you love her and prepare to hear the sweetest sounding “Yes!” of your entire life.

Your mate just scored a major job promotion…
Whether she’s officially the big cheese at the office or just making strides in the proverbial rat race, it’s a fitting evening to indulge in some fromage. The informed servers at Eno(505 N Michigan Ave, 800-971-4654) will happily help you select a wine flight with tasty cheeses to go with it. Congrats!

You’re celebrating an anniversary…
Set the mood for romance by swinging by the Art Institute of Chicago(111 S Michigan Ave, 312-443-3600, artic.edu/aic) on a Thursday evening from 5–8pm, when admission is free. Rather than crowding into a predictable destination—like the Impressionist Gallery—wander into the under-the-radar Ando Gallery in the department of Asian Art. This elegant little room, designed in 1992 by famous Japanese architect Tadao Ando, is dark, quiet and secluded (a.k.a. totally romantic), and it always displays something beautiful. After browsing, walk about 15 minutes north to Trump Tower(401 N Wabash Ave). Splurge on a decadent dinner at Sixteen (it’s your anniversary, cheapass, suck it up), where you’ll get a close-up view of architectural gems like the Wrigley Building and Tribune Tower. If you’re a super high roller, finish your evening by staying overnight (rooms start at $395 a night).

It’s your S.O.’s birthday…
He may not be dreaming of this present, but trust us and give it to him anyway: Take your guy to the revamped Shedd Aquarium Oceanarium(1200 S Lake Shore Dr, 312-939-2438, sheddaquarium.org), where the two of you will get up close and personal with the Shedd’s ten-year-old whale, Kayavak, at the Beluga Encounter Habitat ($250 for non-members, $175 for members, includes admission and a photo, call 312-692-2730 to make a reservation at least three weeks in advance). After donning chest-high waders (dude bonus: He gets to wear jeans on this date), enjoy an hour-long lesson followed by one-on-one interaction with the colossal beluga in a private pool. After an hour of flicking your palm to elicit whale spit and other neat tricks, your guy will be armed with memories he’ll gloat about to his buddies for years to come. Start the reminiscing right away with low-key drinks and grub at Little Branch Café(1251 S Prairie Ave, 312-360-0101). Tucked behind the Field Museum, it’s a mellow spot to seal the birthday mood.

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