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Does Dating in Your City Seem Impossible? Maybe It’s Not!

Yesterday, I was a guest on Art ‘Chat Daddy’ Sims WVON 1690. We talked about how Chicago can be one of the worst cities in the country if you’re  single. The stories are legend about the horrors of the Chicago dating scene.

As a native Chicagoan who has been single, married, divorced and a single mom, I could relate. I’ve dated as a single woman and a single mother. I am one of those sorry statistics.


 Chicago Statistics

WalletHub recently analyzed the country’s 150 most populated cities across 25 key metrics to determine the Best & Worst Cities for Singles in 2015. They included data ranges from the percentage of singles for each gender and various lifestyle characteristics in the regions. Chicago was real low on their list: #133, making it the 18th worst city in America in which to be single.

Marie Clare magazine listed some reasons why this is the case. Men seem less likely to commit in Chicago because of the abundance of women. If you are a single black woman in Chicago, the statistics are even bleaker. For every 100 black women, there are only 75 single black men available. Additionally, if you factor in the growing gay and lesbian community and how many people date outside of race, culture, and religion, we can see why we’re facing a seriously shrunken dating pool.

I see other dating challenges—unrelated to ethnicity, sexual orientation, culture, or religion. And Chicago is not alone in this regard. These days, it can be difficult to date in any city.

Bridging the Dating Gap

 One of the most common complaints I hear from men is that women are unapproachable. But women tend to tell me that men approach them in ways that are uncomfortable, weird, or inappropriate.

Thus, there appears to be a gap in communication. There’s a breach in communication that has created a problem with how women and men interact. This is creating the dating gap.

Here are some statistics for modern dating that hit home with both men and women. Take a look. You’ll see that hope is not lost for bridging the gap when it comes to dating.

“The Dating Scene by the Numbers” from Timeout Chicago Magazine states:

  • Men realize they need to make the first move. In fact, 75% think they should make the first move and 55% of women agree. What this means is men want to talk to women. They wish to approach. This also means women for the most part are open to that and expect men to approach them.
  • Men and women want the same things. What men and women find most attractive in one another are very similar. Both want someone with intelligence, a sense of humor, who is attractive. Looks matter, but attractiveness ranks third— with personality in first place.
  • Both men and women are meeting new people online. Using online services widens the reach for potential candidates. Men prefer Tinder, which is a hookup site; women like Ok Cupid, which is more geared to romance. So both sexes are open to using online dating apps and sites, but each has a preference for a particular approach to meeting people online and to dating in general.

This indicates that singles are indeed looking for love and connection, but men and women are not communicating this well. And when they do communicate the desire to date, the timing is off. Or the way they approach one another is wrong. But since both men and women are looking for the same characteristics in the opposite sex, all hope is not lost. The gap can be bridged.


Here’s What You Need to Know to Date Smarter

Here’s my advice for men: It is okay to approach a woman you are interested in, but think about what you are going to say and how you will say it. Don’t start off with the direct, “Hey you look sexy.” That won’t work.

Instead, try something more indirect such as casual conversation. If the woman’s body language is open, ask her how she’s doing or how her day is going. If you want to go for the compliment, make a nice comment about her outfit, or maybe her smile. But keep it casual and not sexual.

If a woman you are attracted to is with her child, open a door for her or do something helpful. When they are with their children, most women have a lot on their minds. If the conversation goes further with the women, launch into a discussion that would be meaningful for a parent. Integrate these kinds of topics into your conversation. This makes you more relatable to a single mother. It makes her more comfortable, so is a better way to communicate with her.

Women should note how hard it is for men to approach. They have egos, and their confidence can be fragile as well. If a guy says hello, do respond in kind. Smile at him. If you are interested, give him a sign that it is okay to continue the conversation. Men love compliments so if you see something you like about him, don’t be afraid to communicate this. Telling a man he has a nice smile or you like the fragrance he is wearing will make him feel good.

Men also want to feel appreciated. If a man opens a door or expresses a compliment to you, do thank him. If you are not interested in him, tell him you are flattered but not interested. And when you say this, do it kindly. Turn him down the way you would want someone to express such sentiments to you. Rejection is hard for all of us, but doing it in a kind way is only fair. Plus, it helps you to improve your communication with men and opens you up for when the right man comes along.

Other ways in which both men and women can expand dating opportunities include: going to singles mixers in the city, visiting lounges, jazz sets, and cultural events. Take a class or go stag to a party. Get out more, mix up the people you are mingling with. Expand your circle outside your comfort zone.

The truth is, any city can be a tough place to date. But if you know what to do, that can help you change your circumstances. Bridge the communication gap and be kind. Those two things should open the doors for you to a better social life.

Happy Dating!


You are capable of receiving love. There is a relationship that will work for you. Sometimes all you need is a nudge in the right direction. If you are struggling with your current relationship, newly divorced and looking to get back in the dating scene, or single and trying to find the right person for you, maybe I can help. Reach out to me at [email protected], or sign up on my website to receive dating tips and relationship advice. For fast advice, read my book, The Relationship Investigator’s Fast Guide to Successful Dating.

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