First Dates in Chicago

So, you’ve met that special someone; that skip a beat, knot in your throat, palms sweaty someone that might be THE one. What to do? Where to go? Of course, for a first date, from a woman’s perspective (and an older woman I might add), you don’t want to be extravagant or overbearing. A first date should be a nice easy, relaxing, getting to know you kind of atmosphere. An atmosphere that’s conducive to talking, laughing, or if things play out, touching, kissing, cuddling. It’s been known to happen on the first date – – a lot. You can always go the traditional route of dinner and a movie, or dinner and dancing, or maybe just drinks at a local nightclub – – there are plenty in Chicago. These will all suffice and may lead somewhere, who knows where, but is there really any romance, any style, any originality in any of these? I think not. Summer in the city of Chicago, whether it’s a first date or last, needs to be spent outside. Outside in Chicago, along the glistening shores of Lake Michigan. Outside on a first date in Chicago, beneath the sparkling city lights.

Here’s a first date in Chicago suggestion – – an outdoor movie in Grant Park. The younger crowd just has no idea what’s missed with the loss of drive-in movies. Believe me, it was a world distinctively separate from mega cinema malls. It was seclusion and exhibitionism, romance and parties, bad and ohhh so good, but I digress. Beginning in July and running through August, feature length, current and classic movies are shown in parks throughout Chicago, however Grant Park is a perfect site for that all important first date. Just east of the glitz and glitter of Michigan Avenue – – the Magnificent Mile, nestled west of Monroe Harbor, (which offers transient mooring in case you have a cute little sailboat or a jazzed up speedboat, or a lofty, cruising yacht), an easy walk north of Buckingham Fountain, and a feisty hike, or perhaps a dreamy carriage ride, south of the new, spectacular Millennium Park, there is the lush greenery of Grant Park. It’s either the end to a perfect day or the beginning of a lovely night, either way, it’s a first date she or he will never forget.

Ok, let’s set the stage. Remember, this is coming from a middle-aged woman, but does that really matter? Since this summer in Chicago is excruciatingly HOT, you may want to forego the walk around Millennium Park, although the “faces” waterfalls are a great place to cool off if you’re not dressed to kill or too up-tight with the first date jitters. I’ve never tried it personally, but my grandchildren love it. If you decide to bring your water bottles and attempt the expedition, check out the gardens and the Bean (actually Cloud Gate), making sure you go all the way IN the Bean and look up at the faux vortex.

Although it looks like a bean the name Cloud Gate does represent something – – that you can see a phenomenal reflection of the clouds over the lake or, on the west side, misting the skyscrapers. You can impress your first date with the stats that it cost $23 MILLION, $17 million more than planned. Thankfully, it wasn’t City of Chicago (read taxpayers) dollars. But, back to the first date. Let’s say you skip the afternoon festivities because of the heat, and schedule the date to begin around dinnertime. Just south of Monroe at 130 S. Michigan is the country’s busiest Bennigans, and a great place to eat hearty or light, and break the ice over a couple of cold brews or iced cocktails, or even a soda. Afterwards, you walk due east and wa-la, Grant Park. But we have to backtrack just a touch to prepare for the movie scene.

A picnic basket is oh, so elegantÃ?©, but a backpack will suffice. Something to carry your victuals in. Something that will keep a chilled bottle of vino cool, or if you prefer red wine, that really doesn’t matter. The suggested accompaniment is: grapes (red, white or both), cheese (cubed-Cheddar is great, but then so is Gouda, Feta or Swiss), bread (a nice small loaf of French or Italian, or even a couple baguettes), and some sort of pastry (cannolli or baklava fits perfectly). Now this is MY cuisine choice for Chicago’s outdoor movies. Depending on you and/or your first date, it may and can differ. Depending also on your ethnicity and diet. Stuffed grape leaves and falafel, or chopped liver and Challah, or a veggie plate with dip. Whatever, bring something, even if it’s water and chips. And something to sit on. Now, I love the coziness of a blanket on the grass, where you must actually sit within skin touching distance of your first date, and after awhile you either lean against each other, or lie next to each other and intimacy beneath Chicago’s bright lights becomes a probability. However, my old bones cannot handle this any longer so we bring those lightweight, fold-up chairs. If you opt for the closeness of a blanket, bring one that is waterproof at least on one side, so the dampness doesn’t creep up onto your clothes. Especially if you or your date are wearing summer colors of white or yellow or beige. This can be quite embarrassing anytime, but a disaster on the first date.

So, you’re all packed and ready. Whether you stop for a quick bite at Bennigan’s or a sandwich at the Corner Bakery on the corner of Washington and Michigan, head over to Grant Park early so you get good seating. Even though the screen is huge and speakers are strategically placed, it’s still nice to be up front, and the bathrooms are closer. That always helps, again anytime but especially on that important first date. This summers selections are great classics like Rebel Without a Cause, or On the Waterfront. James Dean and Marlon Brando, how can you go wrong? You nibble a little (food or otherwise), you drink a little, talk a little, laugh a little, and just all around get to know your first date beneath twinkling stars and a silvery moon. After the movie, it doesn’t have to end, like in a theater. The romance continues. Take a stroll along Monroe Harbor, dangle your feet in the cool water while you watch the parade of boats – – and people. People watching in Chicago is like nowhere else. Hold hands or cuddle beside Buckingham Fountain and drift with the dazzling light display. Who knows what will become of the next few hours. Regardless, it will be a first date, in the heat of summer in the city of Chicago that neither will ever forget. Enjoy! And good luck!