As much as I love summer dates outside on patios or at the beach, I think it's safe to assume most of us are ready for the weather to change, the scarves to come out, and for dates to transform into something new. I've put together a list for all you daters, both new and longterm, to [pumpkin] spice things up this fall - let's pretend that was at least slightly clever. For all you comfort food lovers, warm whiskey filled cocktail drinkers, and adventure seekers, I've got you covered (and your dates, too.)
For the forever Chicago tourist
Drinks and food are great (obviously), but it's always refreshing to go on a date where they are not the main focus. Switch things up by taking your date to a museum or another Chicago attraction. You've already been to every Chicago museum? Go again - guaranteed you and your date will discover something new. Museums are an easy way to get a conversation going and to learn a little bit more about your date. Not the biggest talker or nervous for the first date? Let the exhibits do the talking! Chances are, your date will also appreciate that you two stepped outside of the dating comfort zone of sitting at a bar.
I think a lot of us might be able to remember field trips to the Museum of Science and Industry as kids. Yet, how many of us have been back to it as an adult - and on a date? My guess is that exploring some science on a date will be just a bit more fun than being chaperoned by your teacher. The Museum of Science and Industry (MSI) itself sets the perfect environment for a fall date: Numbers in Nature is an exhibit that is all about the nature around us from the changing seasons (hello, fall!) to the patterns we see on leaves. The bonus? The Mirror Maze in this exhibit is the ideal backdrop for a quick photo opp.
Skip the small talk on a first date by delving into some deeper (and more interesting) topics; MSI makes this pretty easy. Control your own flight on the flight stimulator, let the kid in both of you come out as you check out the Brick by Brick exhibit (AKA... LEGOS®, and a lot of them), and transport back to WWII as you both experience the U-505 Submarine exhibit, where you'll see the only German submarine in the US. Still struggling to find the "fireworks" between you and your date? Not a problem - head over to the Science Storms exhibit where you'll get to create some virtual fireworks of your own. For some more interaction, you can also take control of your own mini tornado with your date, or experience an indoor lightening storm.
Keep a lookout mid November for some after hours. The museum is interesting as it is, but pair it with snacks and drinks and you've officially won your date over. To give you a little taste for what's to come... the last After Hour's included performances from Second City (comedy is ALWAYS a plus on a date.) Keep a look out! My guess is that fall daters are going to jump on this idea... and quickly.
For the foodie
"To get food or not to get food?" This always seems to be the question on a first date. By date number ten, or two years into the relationship, "where do you want to eat?" becomes the new question constantly asked (I personally enjoy the latter situation.) My rule of thumb: why NOT get food? There is no rule that says otherwise. Especially in fall when flavors get cozier and scream romance. Go on and get your grub on.
Nothing says fall like German food and ciders, and Lincoln Square is literally Chicago's own little Germany. If you don't live up north, a trip out to Lincoln Square is not only the perfect place to get your grub on, but also an excuse to explore more of Chicago and experience something new with your date. At first glance when you walk into Gene's Sausage Shop, you'll think you just took your date to the grocery store... and you sort of have. BUT, wait! Head upstairs to the rooftop where you'll find a bar fully stocked with German beer and cheap bites to eat like pretzels, sausages (did I even need to make that clear?), and schnitzel (which is also fun to pronounce). Cheers! Or should I say, Prost!
Next up, head south on Lincoln Avenue where you'll find dessert in the form of cider, donuts, and cheese plates; find me a better combination, I dare ya. The Northman is doing it right: a whole "novel" of ciders to choose from around the world and a British pub sort of vibe. Create a cider tasting for yourselves and feel free to indulge on multiple orders of their homemade apple cider donuts; trust me, you'll want to.
For the cocktail connoisseur
I'm personally a big fan of drinks on dates, especially first dates! It seems to lighten the pressure and ease the vibe of the date itself. That being said, Chicago is the ideal spot to take a date out for a drink that's a little step up from a rum and coke or a Bud Light; nothing wrong with either of them, but let's step it up a notch here. Fall means that dark-lit bars and speakeasies become more appealing than they already are.
The Ladies Room in Logan square ain't just for lady's night. Take your date to this red and dimly lit spot where you can try a variety of cocktails crafted with liquors, cordials, and bitters you may have never heard of, including cocktails in the form of tea. One of the teas has an ingredient by the name of, Freak of Nature. If that isn't a prediction for how the date may end up, I don't know what is. The space itself is intimate with Japanese printings and pieces of art scaling every wall; consider yourself transported to Japan with your date as soon as you walk into this speakeasy. Want to heat things up a bit? The Ladie's Room supplies the flame - in cocktail form.
For the nature-lover
Is there any better time than fall to take a hike? Forget the sweat and the heat of summer, and pack up your car (and your date) for a day that takes full advantage of the fall weather. Pick a Saturday or Sunday morning to drive out just under two hours to a hiking spot that will have any nature OR city-lover appreciating the scenery.
If you're looking for a day of hiking in the fall, Starved Rock won't let you down with its 2,360 acres of land. There are 18 canyons (and 14 waterfalls) for you and your date to look at in pure awe, and more than 13 miles of trails for you to test out your endurance. If you really want to become one with nature, explore Starved Rock on horseback. Trust me, you'll want to plan a full day here; so come prepared with a picnic. There are plenty of Chicago restaurants that offer picnic packages, so all you'll be responsible for is the blanket. If the date's going well, feel free to spend the night: lodging and campsites are also available!
For the gamer
Fall eliminates our opportunities for patios, but completely opens the door for dive bars and getting creative with "indoor plans." I've always been a big fan of "activities" on dates, especially within the first few. There tends to be a lot of pressure placed on the first date: what happens if conversation isn't going well, do I sound like a complete moron (maybe), how long will this damn silence last?! Rest assured: there are other options for you that don't require constant conversation (and constant anxiety).
Guthrie's Tavern in Lakeview is a date spot that I will always recommend, and for good reason! Guthrie's itself is a dive bar that is fully stocked with board games that will instantly bring you back to your childhood. From Scattegories to Guess Who? to Monopoly, my guess is that you and your date won't have too much trouble keeping yourselves occupied. Plus, a little competition is never a bad idea for a date! Get playful with it, create a tournament between the two of you, and then mull over your loss with a White Russian or hot chocolate from the bar. Oh, did I mention you can also order in food to Guthrie's? Yep, you sure can. Postmates - where you at?
For the crafter
If Chicago fall weather means you're "stuck" inside, you might as well make it as enjoyable as possible! Get crafty with it - and in a few different ways. "Crafting," for lack of a better term, is actually a great way to learn a bit more about your date. It allows you to see their creative side (or uncreative side), and also gives you a more tangible memory of the date itself. Dating long term? These "craft" dates can be a fun way to create something for one another or to share together over time.
By crafting, I mean a couple different things here. In the mood to let your artistic side out? There are a ton of different classes that offer "paint nights" in Chicago. Not to fear for those who still draw stick figures: you are guided through the paint session with stencils and support from the instructor, among all the supplies needed to create your "masterpiece." If all else fails, you and your date can sip on a bottle of wine (or drink the whole thing) instead; BYOB policy is always a plus!
Might I also point out: not all of us are modern day Van Gogh's! In this case, crab your apron and head on over to one of Chicago's man cooking classes. Check out different event calendar's to find a cuisine you both either love or know absolutely nothing about and want to take a stab at cooking it. Brew Camp in Ravenswood is another great option to get crafty with your date as you learn the basics of brewing. Reasonably priced from $10-$30, these classes run about an hour which will give you plenty of time together after the class to drink up.