Finding Love in Chicago Winters


Finding love during Chicago winters is no easy task thanks to everyone’s tendency to go into hibernation. Once the temperatures dip, people seem to disappear, which is understandably discouraging for singles who are trying to meet someone. The good news is it’s not a hopeless endeavor to find romance during this time of year! There are ways to meet people during the cold months, it just takes a little more effort and ingenuity.

Don’t shy away from dating apps. With so many free and affordable options, there is something for everyone. Taking a job takes time…so does finding a quality man! Some of the options for the 30 and up crowd include Tinder (yes, there are quality guys on Tinder), Coffee Meets Bagel and OkCupid (which is gaining popularity). Also, keep up to date. Just like new bars and restaurant open up all the time, so do new dating apps. Who knows, Mr. Right could be just a click away!

Go to restaurants that have community tables. Chicago is a lively city year round, even during the seemingly endless months of cold weather. This new option allows you to eat at the nicer restaurants at a reserved spot for singles such as yourself. If you are feeling shy, bring a friend along. It is sure to be a fun night out regardless!

Join a cold weather sports league. Just because it’s cold doesn’t mean that there aren’t any options to play sports in the winter. Not only can you do past indoor favorites likes bowling and indoor volleyball, but you can do new things like whirly ball and dodge ball. These sports and social leagues have grown in popularity and there is actually a league just for singles, which you can learn more about at

Sign up for a fitness class. If you are active or just enjoy working out, classes are an excellent place to meet someone you are compatible with. Sign up through Groupon or another discount site to try a new class; that way you know there will be other people who are new like yourself. By attending the same class, it shows that you have similar interests and want to take care of yourself. It also means that you will see people routinely, which allows you to develop a spark a guy even if it doesn’t happen the first time you see each other.  Even if you don’t meet someone new, you are still doing something productive.

Keep your eye open while at the airport. If you travel during winter, you may find your special someone at the airport. It may be surprising, but 1 in 10 adults has either dated or known someone who has dated a person they met on a flight or at the airport. Use your travel time to the advantage of your love life and spark up a conversation with a cute stranger.

Remember that in order for someone to approach you, you have to look approachable. Stay off your phone when you’re in public places or at social gatherings and do not be afraid to make eye contact with strangers. Also remember that these tips only work if you put the effort into making them work. Signing up for a dating app doesn’t do any good if you do nothing more than sign up. Going to singles events won’t be productive if you don’t try to get to know anyone there. Dating is supposed to be fun, so dive in and have a blast despite the cold temperatures!


About Stefanie Safran

Stef Safran (aka Chicago’s Introductionista) has been in the matchmaking industry for over twelve years. Getting her start as a Contestant Coordinator on The Dating Game, Ms. Safran learned up close and personal what it takes to find people for both romantic and television pursuits. Gaining further experience in the business, she worked at one of Chicago’s top matchmaking firms and as a “wing man” for Wendy Ralph of Rent Mr. Right Now, where she would scout the room and assist clients with meeting people and getting phone numbers. Committed to innovating the industry, Stef herself went to a matchmaker and saw first-hand what wasn’t being done right. Learn more at