First dates are often stressful, boring or just plain lame. And it's all because your date asked an innocent question: How about a drink?
Sure, yeah. We all want to get a drink. We could deal without a total stranger’s entire life story, though. So, you're in marketing, you're writing a novel and you visited Rome's Colosseum four years ago? Great, we weren't there. Nothing waters down a good cocktail like a cute date rattling off their past and plans for the future.
That's where the activity date comes in. By getting out and going out on the town you automatically have something in common and more to talk about.
Here’s some ways to skip the awkward segues and go straight for the heart.
Go on a brewery tour
Taste-testing is a great way to get to know someone’s…tastes, for lack of a better word. You can freely complain and praise without judgment, plus there’s people watching to be had, as well as a social lubricant to get through conversational dry patches. Chicago has a plethora of brewery tours—Revolution, Half Acre, Lagunitas—take your pick.
Have a picnic in a park
They always say, “show don’t tell.” Well, here’s your chance to do just that. Instead of telling your date why you majored in film and ended up in social work, show them how fucking awesome a simple platter of cheese and crackers is. Bring some drinks that have a story behind them. Bring what you like. Remember, first dates are more about you than the person sitting next to you.
Go to a street festival
Chicago has a plethora of spring and summer festivals that you don’t have to make an entire day of. Check out a beer festival or a cute little street fest. Steer clear of the giants like Taste of Chicago.
Try comedy
Going to a comedy show is great because if the poor sap on stage completely bombs, you're gifted with comedy material you can use to flirt with your date. If the show goes well, it's just plain funny. Not all places have those dreaded two-drink minimums like Zanies and The Laugh Factory, either.
Neighborhood bar tour
Are you the person that goes “out for a drink” and ends up plastered? Boy, oh boy, do we have an idea for you. Honesty. We’re not advising you get downright drunk, simply that you swim in your natural habitat. You can’t hide that party animal forever, you know. Get four straws and two cocktails, drink 'em down and hop on over to the next spot. Try a small-group tour of the local bars.
Neighborhood food tour
On the sober end of the spectrum, a food date is a great chance to try an assortment of small dishes at a few restaurants within walking distance. This is much better than awkwardly deciding how much of the oversized plate of food you should eat at a standard sit-down meal. Try a Chicago style food tour.
Lincoln Park Zoo
This one is stereotypical, but also self-explanatory. The Lincoln Park Zoo is free. You can easily escape (or, God forbid, ditch) your date if they’re a snooze, and there’s plenty of food and drink options available nearby. And there's a new baby snow monkey that’s incredibly adorable.
Grab coffee, go for a walk
No matter how good the coffee, these dates are usually pretty stale. The coffee shop is likely cramped. Have a destination or two in mind before you meet up, order your drinks and get out. You don’t have to share where you’re going beforehand, but you might need to assure your date that you’re not shepherding him or her into oblivion.
Thrifting mission
You need the perfect set of tumblers or you need a new summer hat or maybe you need to do some redecorating. Try on an awful shirt for laughs, get brownie points for looking good in cheap clothes. Be forewarned, you may want to pair this one with another of the above date ideas. If you discover a treasure trove right away or a few thrift stores end up being trash heaps, you’ll want to move on.
Gift shopping
Go shopping for a friend or family member’s birthday. The only catch: The person receiving the gift has to be fun. The viability of this date will be measured by your willingness to buy gifts that all kinds of useless, bizarre, cool and—no pressure—showcase who you are and the type of people you surround yourself with. Don't have a silly friend? Fake it.
Segway tour
This date will show you're able to check your shame at the door and throw some light on your fun side. No one ever said riding a Segway was glamorous, but hey, if your date thinks you're cute on a Segway, you'll look positively dreamy anywhere else.