It’s a date

Looking for creative date ideas to break you from a tired routine with your significant other? We knew whom to ask for help

By Karin Kane

The other day some co-workers and I were sitting around talking about good dates — not day of the week dates, but good, quality, going-out-and-having-a-good-time dates with the opposite sex. Since most of us are in fairly committed relationships, our talk drifted away from the people we’ve dated to the memorable events, or outings, that we’ve been to on a date. Unfortunately, as we chatted, most of us realized that we haven’t been doing a very good job of planning dates.

One guy, Charles, was a fan of strolls along Lake Michigan with bottles of champagne (and if you’re interested, ladies, let me know and I’ll pass on your numbers), but the rest of us didn’t have much to say. After all, it’s not difficult to be creative when you’re first going out with someone, but after you’ve gotten into a routine, it becomes easier to walk to the neighborhood pasta place with a bottle of BYO wine than it is to plan a real date. But as thousands of well-intentioned friends suggest, it’s important to have a real date every now and then!

And for the single crowd, choosing good dating events can be even more important — it’s a way to have fun with someone right off the bat, break the ice and ensure that even if the person you’re out with is dull, you’ll at least have a great time.

My husband and I have been out of the dating scene so long though, that we didn’t know where to start. Fortunately, we happen to know one couple that does a great job of planning fantastic date nights every single month despite the fact they’re engaged and busy planning a fall wedding. So we caught up with Crystal and Dan, Chicago’s best dating couple, to get their tips, ideas and suggestions for our own date nights.

What made you decide to do a “date night” every month? We didn’t feel we were experiencing the city to its fullest potential. We both love Chicago, but we found ourselves going to the same restaurants and bars, or after long weeks at work, maybe not going out at all. One day, we decided to go out with just each other and to go to some place different. We went to Francesca’s on Taylor and then swung over to Bevi Amos for wine tasting. We had a blast, and over a glass of shiraz, date night was founded. Date night had to be for just the two of us and a way to experience everything Chicago has to offer.

How do you choose where to go? Each month, on a rotating basis, one of us will plan the date. We look for unique experiences, activities or events in Chicago or the surrounding area. We try to pair a restaurant where we have not previously dined with that activity.

Where do you get ideas from? We use the internet, newspapers or recommendations from others to plan the events. Usually, we start with a theme and go from there.

Do you have any rules or guidelines? The only rule is we can’t go to the same place or do the same activity unless we are celebrating something special, such as an anniversary. The date night should also fall on or around the 13th of the month, as that was the day of our first date.

What have been your favorite dates so far? Each date night has been special for us. What sets the date night apart isn’t the restaurant or the activity, but the little things that we remember. One of our favorite date nights probably was also the most stressful. After running the Elvis 5k and eating a nice picnic with Potbelly sandwiches in the park, we headed over to Kayak Chicago for a quick kayak lesson before heading out to catch the Navy Pier fireworks. As we paddled our kayaks down the north branch of Chicago River, we were able to listen to the peacefulness of the city. It didn’t feel like we were in Chicago anymore, but instead along a quiet river. The view of skyline was breathtaking. But after we passed the Kinzie Street Bridge, we had to deal with the wake of the large boats and currents that pushed us out to the middle of the river with boats coming from both directions. The round trip lasted about three hours. It was tiring, but sitting on the Chicago River with your arm around your best friend is something we will never forget.

Some of our other favorite activities included a paella cooking class at Café Ba Ba Reeba, wine making class at Round Barn Winery and smoking hookah at Sigara. Some of our favorite restaurants include Meritage Café and Wine Bar, OneSixtyBlue, Moto and Sai Café.

Did you have any least favorites? We don’t have any least favorites, as they have all been memorable experiences. The most important thing for us was to make time for each other.

What are you planning next? We have a couple of ideas but have not finalized them yet. We have thought about a couple’s cooking class, going to Chinatown, watching a movie or concert in the park, seeing a play or going to an outdoor festival.

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