Dating isn't hard. Expectations are.
So let us reset them. Don't worry about setting up the perfect date — just focus on being the perfect date.
With this countdown of Chicago’s top 5 first dates, all you have to do is be on time.
5. Sunset Boat Cruise
Nothing is more romantic than the skyline at sunset, and this cruise from the Wrigley Building to Buckingham Fountain will have her curling up to you for warmth. Afterwards, walk over the garden-style outdoor patio at Howells & Hood and relive the experience over a round of vodka tonics.
Wendella Boat Tours Sunset Cruise, 400 N. Michigan Ave., Loop (312-337-1446). $26.60 here.
Howells & Hoods, 435 N. Michigan Ave., Loop (312-262-5310).
4. Rock & Roll Bowling
For a random experience for the adventurous, take her to this bowling alley/nightclub where you can bond over your mutual hatred of the 7-10 split. Sure you could take her to a club, but this place is way more fun. Where else can you show off your Kingpin dance moves during a laser light show?
Diversey River Bowl, 2211 W. Diversey Ave., Lakeview (773-227-5800). $19 and up per hour.
3. A Day at the Beach
The quickest way to see her in a bikini? Take her up to the more laid-back Montrose Beach, where she’ll be in the mood for a romantic stroll in the sand away from the noisy chaos of North Avenue Beach — especially after you tip a few Mai Tais at the waterfront bar/café known as The Dock.
The Dock at Montrose Beach, 200 Montrose Drive. (773-704-8435).
2. Dinner & a Movie
Take the prototypical first date to a whole other level. Dine in grandeur on the gorgeous outdoor patio of the city’s most romantic restaurant, Piccolo Sogno. Afterwards, take her to the new Logan Theatre where you can keep sharing that bottle of wine right there in your seat.
Piccolo Sogno, 464 N. Halsted St., West Loop (312-421-0077).
Logan Theatre, 2646 N. Milwaukee Ave., Logan Square (773-342-5555). $5.50-7.
1. An Outdoor BYOB Concert
Fill your backpack with booze and take the Metra to Ravinia, a lush suburban park that just happens to host the oldest (and one of the best) outdoor fests in the U.S. Spread a blanket out on the lawn and clink your champagne glasses together as you take in the music and scenery in total serenity.
Ravinia Festival, 200 Ravinia Park Road, Highland Park (847-266-0641). $27 and up here.