3 Great Dates

Appears in the February 2020 issue.

By Cara Sullivan

Win over that special someone with this Cupid-approved, three-date strategy from Tracy Williams of Chicagoland Singles


I personally tell my clients that the first date should not be too intense or costly; the objective should be to get to know your date! I often suggest going to a fundraiser for a local food pantry, family or child in need, or homeless shelter. (Finding an event like this is often as easy as a quick search on social media.) Not only are you doing something that is heartwarming and appreciated, but you’ll also be able to immediately tell if your date is giving and open to helping others.


For a really fun and original activity, spend an afternoon going to a few local estate or garage sales, or go to a nearby thrift store. Pick a neighborhood that you haven’t been to and set a budget of $25 each. The objective is to get a good deal and find something really unique, which makes for a great conversation!  You’ll find out so many things: what your date thinks about other people’s possessions, what they’re interested in and sentimental about, if they’re “too good” for a silly adventure or something secondhand, how are their negotiation skills, and, ultimately, if they had fun and enjoyed spending quality time with you.


At this point, you’re probably feeling little more comfortable and at ease—you’ve made it this far, after all—so it’s time to add a little alcohol and/or closeness. Going to a craft brewery, a wine tasting, or a cooking or dance class are all high on my list of recommendations. Chicagoland Singles has hosted several events at Lynfred Winery, Lucky Monk, Billy Bricks, Fred Astaire Dance Studios, and Arthur Murray Dance Studio—all easygoing spots where the conversation should flow naturally. 

Dating Hall of Fame

When it comes to matchmaking, Williams has seen it all—so we asked her to share the best of the best and the worst of the worst. Drumroll please …

Best match of all time: “An 82-year-old man who has to leave wherever he is before 5 to go home and take his little blue pill, and a 79-year-old woman with a fun dating mantra: ‘Sex is never out of the question.’ ”

Worst date of all time: “The guy picked up his date, then offered her leftovers from a drive-through for dinner, and gave her laundry detergent from the back seat of his car.” [Editor’s note: Yes, that was the entire date.]

Photograph by Olivia Kohler