Instead of running the typical play and taking her to a Starbucks or Caribou Coffee, opt for a something a little less commercialized and check out these hot spots around town.

Jupiter Outpost
1139 Fulton Market Avenue

An outfit that always has a place to sit, relax, and sip on that liquid coffee bean.  They also have food so if your date lasts longer than your drink, you can fill your belly by choosing from their well rounded menu.

Julius Meini
3601 N Southport Ave

Great place for coffee or even brunch.

Savor the Flavor
2545 N Sheffield Ave

Small place that is cozy and comfortable.

Bin 36 is a great American cuisine restaurant that holds an event about once a month called “Movies in the Loft”.  While dinner and a movie might be a little cliche, it is definitely a date that will occur at some point in your fresh new relationship.  If you’re going to do it, do it in style…

Instead of taking your crush out to dinner and cabbing your way to a movie theater, why not kill two birds with one stone?   These events have a 3 course meal coupled with some wine that will keep your belly’s pleased while your eyeballs are entertained.

They play classic movies, the two upcoming being ‘Guess Who’s Coming to Dinner’ and ‘Bottle Shock’.

The next event is coming up on November 22nd, for more details click here.

Overall – 4/5 Stars

The Vic Theatre is typically a concert hall but on their off nights they’ll use the space to project a movie and fill your belly with cheap beer.

They play solid movies that range from new releases (the Hangover-which if you haven’t seen it, get out from under your rock and GO) to classics like Animal House and Office Space.

Here’s a link to their website: Brew and View

Overall – 4/5 Stars

So to keep with the theme of the month, this week’s date idea involves Halloween festivities.

This week’s date ideas include: Apple orchards, pumpkin patches, hay rides, and haunted houses.

Instead of doing my typical breakdown of pro’s and con’s, here are links to places to so you have a handy guide to take that special crush.

Apple Orchards

Pumpkin Patches (parks on the right)

Hay Rides

Haunted Houses

You can’t go wrong with any of these types of dates.  They’re a great way to get outside and enjoy the weather before it gets unbearable.

If I left anything off the list, drop it in the comments!

Somewhere between that Architecture tour and dyeing the river green on St. Patrick’s Day, you’ve seen people floating down the river where it seems they have no business floating.  I’m not referring to dead bodies that the mob disposed (cement, remember?), I’m referring to the happy go lucky people floating in kayaks.

This week’s date idea is kayaking.

Let’s break it down:

Pro’s

Unique - This isn’t your typical dinner and drinks date.  Something fresh will keep you both on your toes, even if you’re both beginners.
Active – You may not break a sweat, but it’s still something that will get you pumping some of those muscles to keep you moving.  If you’re the outdoors type, it’s a great litmus test to see if your date will be fun and along for the ride, or will drag her heels and drop and anchor with her attitude.
Teamwork – Getting a tandem kayak will get you guys communicating on where you need to go and how you need to get there.  It’ll get you talking and hopefully jet-set you on getting on the same wavelength.

Con’s

Inactive person - Your date could be as active as my fish who does a great impression of the dead man’s float.  If she’s not having fun, you’re not going to have fun.
No chemistry test - Not having any real close interaction is going to make it tough to decipher if you have any real chemistry.  Of course you’re going to want to build that sexual tension, so make sure whatever is lined up next will allow the two of you to move a little closer.
Short - Places in the city rent kayaks by the hour, so even if you do decide to rent for a few hours, it’s still a pretty short date.  Like I just mentioned, just make sure you have a plan of attack on the next destination.

Even if this isn’t the best first date, it’s definitely a good option after you’ve gone out a few times.  Something new, something fresh, and it gets you outside and working together.  Just make sure you don’t tip the kayak…

Here are a couple places you can book your kayak – Kayak Chicago, Chicago River Paddle, Wateriders

Overall 3/5 stars

Been on a good date recently?  Post it below!

This weeks date idea is cooking classes.

Let’s break it down:

Pro’s –

Intimate – Food can be extremely sensual in nature.  Using all your senses to make your meal, you’ll have all pistons firing at once.  Getting to know each other will also be a smooth dialogue with all the treats floating around.
Dinner date – This can knock out a good night together.  The two of you will go on a delightful tastebud rollercoaster throughout the evening, no additional planning necessary!
Chemistry test – The way you work together and converse can be a great sign on how well those love ingredients are mixing.

Con’s

No way out – If your date sucks, then you’re basically S.O.L.  This is when playing with your food becomes more than just a past time, it becomes your best friend.  By the way, doubling the heat of the oven does not mean you can half the time you throw it in there.
Expensive – While dinner, drinks, movies, etc can all add up to be the same.  Classes, drinks, and sometimes corkage fees can all add up quickly.

Cooking classes are overall a great date.  This would probably be best reserved after you’ve gone out at least a couple times, but either way, its a great way to spend an evening.  Roll up those sleeves and show Giada how its done!

Here are some places to check out for cooking classes in the city: Partiesthatcook, the Chopping Block, and Wooden Spoon.

Overall 4/5 stars

We could all use one of these days every now and then.  While that movie has plenty of date ideas scattered throughout (ball games, obnoxiously fancy restaurants, and doing a rendition of Danke Schoen on a float), the countless museums around Chicago are all possible date locale’s for that first time encounter.

Let’s break it down…

Pro’s

Conversation - Being the fine purveyor of art that you are, there will be plenty of conversation to help move the flow along for the date.  From the various sculptures, inscriptions on tablets, or even talking about how each painting is “made up of really, really, ridiculously, tiny little dots!”, each room you enter can bring about a brand new topic.

Culture - Compared to hanging out with each other and watching ‘Keeping up with the Kardashians’ or ‘America’s Got Talent’, moving through a museum will activate that little gray matter that rests inside that skull and both of you might learn something new.

Interaction - Some places, like the Shedd Aquarium or Chicago History Museum, will have small little stations where you can stop and use some interaction to learn or play around with a little history.  While this may not be your next daily ritual, every now and than it’s good to reconnect with the kid in all of us.

Con’s

Boring - Let’s face it, it’ll be difficult to make each other laugh to the point where you’re spitting up liquids.  Also, either party could completely hate museums because they aren’t the most stimulating and exciting places on earth.

Short amount of time - Depending on how fast you fly through, these museums can take an whole day to walk through, or as short as an hour depending on your attention span.  Make sure to have a backup venue to fly to next.

Slow Pace - The slow pace and quiet atmosphere can be a drag if there isn’t too much conversation flowing back and forth.  This can paint either of you as boring or non-interested.  Don’t take it out on each other, it could just be Goethe’s Faust summary that…zzzzzzzzzzzz…….

This is is a decent date that is good for killing some time during the day.  It’s always good to venture off into places that you may not visit on your own.  Just make sure to pack some personality so you’ll both be entertained while journeying your way through these mind morsels.  Here’s a list of museums around Chicago.

Overall 2/5 stars

There are many different flavors of festivals out there.  From relaxed culture centric, wine festivals, to great opportunities to meet other singles at the Old St. Pat’s fest.  Whatever you are looking for, these festivals are a great place to take a date due to the high level of interaction, social aspect, and the relaxed atmosphere.

Here’s the breakdown:

Pro’s –

People Watching – Walking around at a festival rivals the entertainment walking around at an airport.  Somehow it always seems to draw the most interesting of people.  Whatever your style is, you’re bound to find the opposite at different festivals, and that always makes for great people watching.

Easy Conversation – With so much going with the food tents, exhibits, and music, you won’t have to rely on the notes you wrote on your hand to keep the conversation flowing.
Group Interaction – Meet your friends there or make new ones.  Festivals are always fun in big groups.  You can even see how your interest works with all the interaction.

Con’s –

Chicago Weather – We all have heard it… if you don’t like it, just wait five minutes.  Well for those Lollapalooza go-ers this year, five minutes never came.  Despite the killer music, the rain and heat were hard to ignore.  You are at the mercy of the weather… rain, shine, heat, or random act of snow, so be prepared to make last minute changes if necessary.
Less focus on each other – With so much external interaction, the date will probably be more about what is going on rather than getting to know each other.  This can be a good thing later on down the dating path, but for first dates, curiosity is an ever-present thought.

While there are some small downfalls to a festival, it is overall a great place to take a first date.  There is a lot to talk about and it can end up being a great time interacting with one another instead of the traditional dinner date.

Click here for a list of upcoming festivals.

Overall 4/5 Stars

Today’s date idea: A Comedy Show

Pro’s –

Humor test - You’ll get a feel for their humor.  If you’re laughing at the same times, it’s a great sign that you’re both on the same wavelength when it comes to humor.  This can sling the doors open to favorite TV shows, movies, and embarrassing stories of the past.

Laughter - This is key on a date.  What better way could you have it?  The pressure is off… sit back and let someone else help release those all important endorphins.  It’ll get both of you in a good mood and shed a positive light on the evening.

Talking points - Chances are the comic(s) touched upon a variety of subjects.  This gives great conversation pieces for the rest of the night and you’ll learn that much more about each other.

Con’s -

Bad comic - The show could be as exciting as watching Curling on a Saturday night.  *tap tap tap* Is this thing on??

Price tag - Depending on the venue, tickets, drinks, and whatever may follow.. the night could have you making multiple trips to the ATM.

Less Interaction - Most of the eve is going to be taken by the brave soldiers on stage, so that can eat into your ‘we’ time.

With a comedy show, the pro’s definitely out-weigh the con’s.  A night almost gauranteed filled with laughter is a great way to get the juices flowing and both of you laughing all the way to your next destination.  A couple places to check out around the city could be Zanies, The Second City, or even The Edge.

Overall – 4/5 stars

Once he had her hooked in, much like the underrated caliber of Subway Choco-Chip cookies, he threw down the surprise of a century.  He asked her to a wedding… for a first date.

Now I’m not too sure what was going through this guy’s head.  How does asking a girl to meet your family, entertain your friends, AND get to know you on first date help your chances?  If anything, something like this will get a girl running faster than if she had the hounds of hell nipping at her heels.

So this inspired me to come up with a weekly treat for these people.  We’ll come up with ideas for a potential date and discuss the pro’s and con’s.  Since I’m not creative with names, we’re going to call the series “Weddings are a Terrible First Date”.

Now I would start with the dinner and drinks, but that’s too obvious.  Plus, dinner dates are always awkward for a first date.  Even if it’s a comfortable atmosphere and you can pick the locale to suit your tastes, you can always spot a first date couple out to dinner.

There are always two different types of eaters… the first date eaters and the everyday eaters.  Physical body language, the use of utensils, and the close guarding of either of you not wanting to look like a greedy pig is always an element that both of you must handle.   Stick to dinner as a second date.

Today’s date idea:  Live Music

Pro’s –

-  You can get a feel for someone’s musical taste.  Music is the soundtrack to life.  Pick a random location, random night, and random band.  Love the music or hate it, both of you can become music critics overnight.

-  Lots of interaction.  These venues are a great place to people watch.  You can see how your personalities mesh out in public without having all the attention squarely on the two of you.

-  Built in conversation.  With music and bands, people can talk forever.  Music is one of the few threads common to the entire world.  You can get to know someone very well by finding out their music tastes.

Con’s –

- Loud atmosphere.  It will be hard to converse while the band is playing, so conversation may be limited in between songs.  Stay away from deafening your date by screaming in their ear all night.

- Awkward dance moves.  Should you dance wildly with your arms flailing?  Should you casually sway?   Head straight to the pit?  This one will be an executive decision, best to take note of the crowd and follow suit.

Overall  5/5 stars

This is a great date idea because of the interaction and getting to know each other factor.  Some great places to check out are Double Door, The Metro, or Martyr’s.  There are plenty of small venues to choose from in the city which can suit your taste.  Discover a very important side of your date throughout the night and if it doesn’t work out, maybe you’ll find your new favorite band!

Have date ideas you’d like to share?  Good ones?  Terrible ones?  Don’t be shy and email them to parag@crushme.com!