We went to Green Dolphin Street for our night of class.

It was a nice, relaxed dinner while listening to a fantastic jazz band.  I felt like I was in the backdrop of an old film… where I should have been wearing a top hat and trench-coat amidst a cigar-filled room.

Here are a couple places to check out around town for some top notch jazz.

Andy’s Jazz Club

Downtown and right next to a bunch of other bars and spots to hit afterwords.  Great spot for dinner and a cozy setting that sits you right next to the band.

The Joynt Chicago

Dark and sexy, this place is a nice spot for a cocktail with some soothing background music.  The music has been stellar and the overall vibe is very cozy.

Kingston Mines

This is more of a social spot.  Open late and plenty of room to spread out.  There are two stages here that trade sets hour after hour.  So if you don’t get a good spot the first time around, hop over to the other side and feel that music!

The Violet Hour in Wicker Park.

This hidden gem has a dark, trendy atmosphere that is sure to promise for a pleasant evening.  Even if you might confuse yourself for being in a giant game of Tetris (the high backed leather chairs look like “L’ pieces and all tables are small perfect squares), the drinks are impeccable and the intimacy is just right.

While I wouldn’t say this is an unknown spot from reading the crowd, it’s for sure a good place to stop by for a quiet evening of getting to know you.

The Violet Hour – 1520 N Damen Ave

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.

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!

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