Category Archives: date ideas

I just met Mr. Right… for you

 I have the unique view into many single mens (and womens) dreams, hopes and desires as a personal Chicago matchmaker and ladies, let me tell you that the good ones aren’t all married or gay. Just today I sat down for a first meeting with a successful man in his mid 30’s.He’s attractive, just over 6 feet with blonde hair and blue eyes. He is built like an athlete but doesn’t spend time in the gym though he does run ever morning rain or shine. Don’t worry ladies, he owns his home and gets along with his mother and his ex mother in law, he hates to cook but loves to clean. This catch has a great personality, puts people at ease with an upbeat personality and light-hearted humor.  He also hasn’t had a date in just over a year.

Why?  Because he doesn’t believe a great gal would want to date a single dad who went through a bitter divorce. He has full custody (that he didn’t have to fight for) and raising a five-year old daughter consumes most of his free time.

As a matchmaker I get to see into people’s life, they share things with me that they may not share with even their best friends. All the guys in the office think Mr. Right is dating a new chick every weekend. He says he has never told anyone he’s been on dates, but people assume and he never wanted to squelch the rumors. In his own words “The dating life the buddies at work think I have is much more exciting than what the truth is, so I never really set them straight.”  He won’t go out to speed dating, or even a nuts & bolts party because he doesn’t know what to do or expect and frankly, he’s scared. This is where I come in. I get to learn a little more about Mr. Right and help introduce him to a great match.

The first meeting will be casual, I’m a huge fan of a first date activity such as mini golf, ping-pong, bus tour of Chicago, etc. The activity will give them something to 1) talk about and 2) do. Having a three-hour dinner date sitting across the table from a total stranger can be very intimidating, especially for a guy who hasn’t been out on a date in a year. I’ll let you know how his first date goes!

Chicago Date Idea #363 (Free date idea)

Take your date to the Museum of Science and Industry. It’s affordable and some days it’s even free!

A lot can be learned about your potential love interest on the way they interact with you and the exhibits. If you are looking for above average intellect and your date does not know the difference between “science” and “industry” you’ll find out fast here.

Another bonus about a museum date… if the two of you have nothing to talk about and there is not a “connection” you’ll feel less awkward being quiet here than over dinner or coffee. You can always discuss the exhibits.

I’m a little excited because they hae a new, cool exhibit from the Muppets!

“Get a rare peek into the imagination of Jim Henson—a brilliant innovator and the creator of Kermit, Big Bird and other beloved characters. This exhibition features 100 original artworks, including drawings, cartoons and storyboards that demonstrate Henson’s talent as a story teller. The exhibit also documents Henson’s process of “visual thinking” through renderings, photographs, documents, puppets and film.

View the iconic puppets created by Henson, television and movie props, photographs of Henson and his collaborators at work, as well as original video productions and experimental films from Henson’s early career. You’ll also get an opportunity to express your own inventiveness through a series of fun and original hands-on activities.” -Museum website

The charge for the Muppets is $5- even on the free days.

Museum of Science and Industry
The Museum of Science and Industry is free  to the public on various dates throughout the year. The museum is open Mon–Sat: 9:30am-4pm; Sun: 11am-4pm; Omnimax-only tickets on Free Days are $9 for adults, $8 for seniors and $7 for children. Normal prices apply for other features;

Free Days 2011:
January 3-7, 10-14, 17-21, 24-28, 31
February 1, 8, 14, 15, 22
June 1, 2, 6, 7, 8, 9
September 6-9, 12-16, 19-23, 26-30
October 31

Chicago Date Idea #364



Cheap, easy and you can win some “cool” prizes. Taking your date out for skee ball is one of those things that you’ve got to do with total confidence or you just aren’t gonna pull it off.

Where to play in Chicago? Check out this Yelp link. Lots of fun places in Chicago and the suburbs. My favorite is Dave & Busters in Old Town.

Chicago Date Ideas #365

Every girl I know wants to be taken on those carriage rides in Chicago, up and down Michigan Avenue. You know… those slow horses that cause you to miss the light that are filled with tourists and 18 year olds on prom night? Well… thats what she wants to do tonight. I Promise. Rates start at $40 a half hour (may be negotiable, but don’t haggle in front of your lady). It doesnt’ matter if it is a Monday night or a Friday night, surprise her and take her out on the town. After the carriage ride, take a stroll down Michigan Avenue, keep her on the east side of the street if you don’t want her wandering into Tiffanys, but wouldn’t mind wandering into La Perla. 😉 Finish the night with hot chocolate at Ghirardelli Chocolate on 830 N. Michigan. 

Date night cost $60-70  (Ride, tip, hot chocolates)