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“Date night” took a backseat this summer, as my guy’s busy gig/triathlon schedule and my cheerleader/work schedule filled almost every evening. On the evenings we were both free, we just wanted to relax and veg on the couch – a date, yes, but not the most exciting one, and certainly not taking advantage of all that this amazing city has to offer!

Totally ready for a Date Night Marathon!

Now that it’s autumn and our schedules are back to normal, we decided to make up for our date drought by going on a Date-a-Palooza: A three night date bender that would give us the bonding time we missed out on over the summer.

After much thought, we chose the following schedule:

Friday: Dinner at home, a night at iO Improv to see the Improvisational Shakespeare troupe

I’ve only been to iO Improv a couple of times, and have never been disappointed by the comedic talent there. What better way to end the week than laughing out loud to the musings of the Improvised Shakespeare troupe? I had no idea what to expect, and my guy was a little afraid that comedy in iambic pentameter would not only be confusing, but just wouldn’t work. After much debate, we bought tickets, took a shot of whiskey (Okay, maybe two…cheers!) and made our way to Wrigleyville.

At the theatre, the IS troupe asked the crowd to shout a title for a play that they would make up on the spot. “Julius Pizza” was the title most shouted and then we witnessed the world premier of a brilliant Shakespeare play, complete with the best prologue with pizza references that was funnier than anything Shakespeare has written. Watching the all-male troupe play female parts and giggle at their own jokes as they materialised made the whole night thoroughly enjoyable. I was amazed how in sync the men were, never cutting each other off and always having the perfectly timed aside that both jived with the current event, and set up the next scene brilliantly.  There ended up being,  as I expected, a lot of jokes about the male member, but nothing too eye-rolling. We left in good spirits, wishing that we remembered all of the lines we laughed at, and agreed that it was one of the best improv shows we’d ever been to!

Saturday: Green City Market and an extended dinner/drinks at Hopleaf

A visit to Green City Market makes a great day date (just don’t ask your guy/gal to meet you at 7am) because there’s endless amounts of people/dog watching, ready-made delicious food (Sunday Dinner’s burgers….yum!), live music, chef demos/tastings, and it gives you a great excuse to invite someone to come back to your place…for a local, seasonal home-cooked meal, of course! We hung out and picked up some local fare to make homemade peach jam and a delish lunch.

Dinner at the Hopleaf is a great date for anyone who likes great craft beer and the bar’s specialty…mussels and fries! The side of stilton mac-n-cheese is the best, ever(!) and the venison meatballs…well, they were tender and earthy without being even a bit gamey. We agreed that the vibe of Hopleaf (there’s no blaring music, the lighting is soft, and if you score a table on the upstairs Mezzanine, you can look over the restaurant and people watch while feeling like it’s just the two of you. Romantic? Not quite…but it is intimate and the food is to-die-for!!!!

Sunday: A 6 1/2 hour movie marathon: Brew and View at The Vic.

A TOTAL GEM! How I walked by The Vic every day and DIDN’T partake in Brew and View is ridiculous!!! You MUST go here! The catch? You pay $5 or $6 (depending if they’re offering two or three movies, respectively, that week) per person to watch two or three movies back-to-back(-to-back). The movies are either cult classics (think Grease or Rocky Horror Picture Show), or second- and third- run movies, but if you’re like me, you probably didn’t get around to seeing them the first time they were out.

I took a survey on their website and got a 2-for-1 admission, which made TWO tickets…$6. To top it off, there were drink specials, a concession stand and you can order in food from their list of delivery spots. There’s no shortage of good delivery in Lakeview, so it’s totally worth it to order something. Talk about a cheap date! Brew and View is totally casual, you can talk during the movies, make fun of them (not in a hushed voice!), eat and drink a beer while enjoying someone’s company. We watched all three movies (a 6 1/2 hour affair!), but it was perfect for the dreary weather we had on Sunday.

We left the theatre with sore butts and limbs that had only recently “woke up”, but we also left laughing as we recapped silly movie moments and patting ourselves on the backs that we had found such an awesome date place. We’ll definitely be back before too long – hopefully bringing a crew along to brew and view with us!

If you have other great date ideas, let me know! In the mean time, Trev and I are booked for a tandem kayaking experience down the river….I’ll let ya know how it goes!!!

Yay for Chicago! Until next time…

Dev :o) xx