As the weather turns cold and grey in Chicago, it’s time to get even more creative with dating ideas.

Dating By Wegs

Rule #8:  Don’t Let the Weather Stop You

So, I remember when I was single between marriages the first time.  As I said before, I’ve been through a few long Chicago winters as a single guy.  It can be tough.  However, if you have a willing date to actually leave the apartment, then nothing really changes in terms of your dating mindset.  You still need to be creative.  You should be having fun.  In fact, I recommend using the elements to your advantage.  As I continue to promote the glories of Chicago, I’m sure you have unique features that your city can provide during the winter months.

Beyond dating, I’m a firm believer in maintaining your routine all year round.  The term “winter blues” happens for a lot of reasons.  For some people, winter blues is a real thing called “Seasonal Affect Disorder” or SAD.  For people struggling with winter blues or SAD, the #1 reason is the lack of sunlight.  Of course, it is hard to simulate sunlight when it is a dark gloomy day.  However, for me, I do my best to continue to walk at lunch time to get my blood flowing and the limited Vitamin D getting in my pores.  You can always buy one of those sun lamps that is supposed to help people through those issues.  However, for me, I think the main issue is that people become way more sedentary in the winter months.  They stay at home on the couch, instead of venturing out.  They may do movie nights in, instead of getting out to their friends or family members.  Lastly, if people exercise avidly in the spring and summer, then that gears down.  Well, I’m here to challenger you to be the one who defies Old Man Winter!!  If you are a gym person, then continue to work out at the same clip.  Be that person who organizes the movie night at your house, but invite over a bunch of friends.  Or even better, do some fun activities with friends where you move from apartment to apartment or condo to condo (A Progressive Dinner, perhaps).  To me, the best time to do one of those pub crawls is in the winter, since the bars are not as packed this time a year.

On the dating side, I have plenty of ideas on how to brave the winter cold and still have fun doing it.

                                                                                     (One of my top winter activities – why not make it a date?)

  • Outdoor Activities:  No reason to be afraid of winter, if you can’t beat winter, then play along.
    • Ice Skating – In Chicago, there are several outdoor skating rinks that you can enjoy.  There is nothing like the exhilaration of gliding on the ice on a crisp winter night with someone you like.  Plus, if you are an experienced skater, then you can help your date learn and they have to grab on to you.  If you can’t skate, then it can be a mutually challenging, but fun experience.  I actually started to skate when my daughter was small and have gotten pretty good over the years.  Plus, you work up a good appetite for a nice meal afterwards.
      • Premium Rinks – Millennium Park – https://www.cityofchicago.org/city/en/depts/dca/supp_info/millennium_park10.html and Maggie Daley Skate Ribbon – https://maggiedaleypark.com/things-to-do-see/skating-ribbon/ – now I’m excited to see that these rinks are now FREE if you own your own skates!!  If you do have to rent skates, then it is $13-15/PP.  Both these rinks open Friday, November 16th and stay open until March 10th.
      • Neighborhood Rinks – As much as the big rinks get the publicity and attention, I really enjoy heading over to my local rink for both exercise and a fun skate with a date.  Not to get sad here, but as some of you know, my soon to be ex-wife and I really enjoyed skating together and got married on ice (reception anyway).  So, as I have braved the world of dating again, I will not hesitate to skate with a new person.  Gotta get back on the proverbial horse.  Warren Park up North is my spot, but check out a rink near you. Most rinks open around Thanksgiving and close by the end of February and are free with your own skates with rentals more reasonable at $6-8/PP.   https://www.chicagoparkdistrict.com/parks-facilities/ice-rinks
    • Sledding – If you are even more adventurous and there is a good snowfall, then why not put a little Pam on an cookie sheet or grab a cheap plastic saucer and hit one of the many sled hills in the area?  There are several parks in the area with hills, in the city, the big one is at Montrose Beach Park, there is another at Warren Park further North, most suburbs have one park with a hill.  Sledding, unlike Skating, requires virtually no skill just a little moxie.  Who could say no to a little sledding and a solid cup of hot chocolate on a nice snowy Saturday during the winter?
  • Cultural Options – the winter is such a good time to enjoy the great museums of Chicago.  Of course, weekends will be more crowded, however it’s a good time.  Here are some of my favorites.
    • Art Institute of Chicago – https://www.artic.edu/ – Prices start at $16 for Chicago Residents for general admission.  Special exhibits will cost more.  Free Days are every Thursday from 5-8 PM for IL Residents.  Could be a nice date night starter.  Located right off Michigan Avenue with some nice restaurants right across the street and to the North.
    • Shedd Aquarium – https://www.sheddaquarium.org/ – Prices start at $19.95 for Chicago Residents.  Free Days for 2019 have not been listed, but are available for IL residents.  A little isolated in the Museum Campus, but the South Loop is not far at all with tons of dining and bar options.
    • Field Museum – https://www.fieldmuseum.org/ – Prices start at $24.  Free Days coming up for IL Residents include Sunday, November 18th and December 16th for general admission and discounted all access.  Just like the Shedd located near South Loop.
    • Chicago History Museum – https://www.chicagohistory.org/ – Prices start at $17 for Chicago Residents.  Museum is free every Tuesday for IL residents and several Commemorative Days.  Located close to Old Town that has a lot of nice bars and restaurants.
    • Museum of Science & Industry – https://www.msichicago.org/ – Prices start at $19.95 online.  Museum free days for the 2019 schedule has yet to be released.  Located in Hyde Park which has a really nice bar and restaurant district on 53rd Street.
  • Seasonal Options – There are so many fun activities to do in Chicago during the holidays that can become nice dates.  These are very Christmas centric, so please share other cultural events for Hanukka and Kwanzaa or other Winter Solstice celebrations in the comments.  Here are a few:
    • Christkindl Market – http://www.christkindlmarket.com/ – I was surprised to learn there were multiple locations of this one, as I’m most familiar with the Daley Plaza one.  The market is a German inspired market great for shopping and getting some good food and of course some alcoholic beverages.  A solid meet up spot after work during the week for a date.  The Market opens November 16th and runs until Christmas Eve.
    • ZooLights at Lincoln Park Zoo – https://www.lpzoo.org/zoolights-presented-comed-and-invesco-qqq – What could be more romantic than walking through Christmas lights in a Zoo?  Well, maybe that’s just me, but it is a great way to be festive and outdoors in a pretty setting.  The Zoo Lights are on display starting November 16th until January 6th.
    • Music Box Double Features – https://www.timeout.com/chicago/movies/music-box-christmas-double-feature#tab_panel_3 – If you are all about Christmas, then how about checking out a double feature of some Christmas classic films – White Christmas and It’s A Wonderful Life – $15.50 (single movie) or $24 for the Double Feature?
  • Classes – Another whole class of activities that you can do during the winter months are classes.  Again, break out of that comfort zone and try something new:
    • Workouts – I’m thinking a Spin/Soul Cycle thing or maybe even a Boxing class – using that competitive, endorphins theory again
    • Art/Cooking – There are classes to learn to paint, pottery, or even cooking you could look into
    • Dancing – Maybe not a great first date, but a 2nd or 3rd if you want to spice things up.  I’m a huge proponent of dancing, so find a local bar that does a salsa lesson then open dancing afterwards or something more obscure like square dancing.

As I come across more fun options, I’ll put them in subsequent blog posts.

So, I wish I had a dating story associated with the above, but I do not.  I have had a couple nice dates of late, but I want to be sure to get approval to share such experiences, as the dating is on going.  I will share a story or two in the coming posts related to the options above as I explore them.  Also, I will be taking next week off the Dating by Wegs section of the blog with the Thanksgiving holiday.  I wish all of you readers out there a happy holiday with family and friends.  I will be going to Vegas for the first time in my life, but not the conventional way, my sister lives out there and we are meeting up to share the holiday with them next week in their home.

Alright, enjoy your holiday and don’t let the progressing winter keep you from being the best dater you know.

Wegs

 

About the author

I'm a 49 year old, twice divorced guy with a 20 year old. The blog has morphed a bit lately. Not just sports or dating, social commentary and now some stories from my past experience.