Before we get started on the dating part of this interview, you were born on the South Side of Chicago. Your amazing stand-up special, “Chicago I’m Home,”  in which you are Director, Writer, and Star, focuses on your growing up there. All of which is great. But, perhaps the greatest part of this is that you have pledged to donate a significant amount of proceeds from your comedy special to Chicago Public Schools and Chicago Charter Schools.

How did you come to this decision and what is your ultimate goal?

I’m originally from the South Side of Chicago, where public schools in the inner city didn’t have a lot of resources. Growing up as a kid, I always wanted to find a way to give back to Chicago, specifically to children who were like me. So, when I released my special, “Chicago I’m Home,” I immediately wanted to touch the lives of Chicagoans by raising money to give back to Chicago Public Schools.

Now, I have to let our audience know right away that you are married. Correct? How long have you been married? Children?

That is correct. I am happily married to my wife Jasmine. We have been married for 4 years. We do not have children, but I do have 3 children from my previous relationships. 

How did the two of you meet? 

I first met Jasmine at UCLA where she was a student and I was playing piano for a class she was in. I later got booked to host an event for her sorority, Delta Sigma Theta, that she happened to be at. We went out to the movies that night and have been together ever since. That was on November 13th 2010. 

How long did you date before making the decision to get married? Who brought up the topic first?

We dated for five years before we got married. She never really talked about marriage and that’s what made me want to marry her even more. But that’s mainly because she was so driven in her education. I was thinking about buying a house and I knew this is where I wanted to be forever so I thought I might as well make it official. 

As you think about first meeting your wife what is the one thing that really stood out about her that you were drawn to?

Her intellect was what it was that stood out to me (and her big booty lol). But, mainly her intellect. 

As a single man was there anything in general that you found attractive in women?

Other than visually. Women that were confident in who they were but were also willing to allow the man to be a man. Someone who is open to constructive criticism and was open to grow with her mate. 

As a single man was there anything in general that you found unattractive in women?

Insecurities for sure. Women who were arrogant or stuck-up, shallow. 

You may have seen the online discussion some weeks ago about a guy who wanted to meet a woman in a parking lot, with that parking lot hookup being considered a “date.” Any thoughts on this?

He obviously didn’t trust her lol. I have to have more context on this. With this information, it definitely didn’t seem like a date, but I would like to know more information on why the hook-up was in the parking lot and what his thoughts were before I draw any conclusions.

What do you think about online dating? Do you believe that it is more beneficial to men or to women? Why? 

I think it’s equally beneficial to both. I think online dating is great. I feel as though you get to see who that person is without the awkward first date; asking all these random questions to see if you all have something in common. It gives you a jumpstart to having an easier and lighter conversation when you do finally meet. I think it’s a great tool for people who aren’t really social or don’t get out a lot because they have busy lives. 

As a comedian you travel a lot and you’ve seen a lot. In the different countries to which you’ve traveled, can you think of any telltale signs that a man reveals when he is definitely interested in a woman, regardless of where you are in the world?

He makes it his business to try to be around her physically someway, somehow. If he really likes her, he is going to find a way to be around her. He just wants her to be in his presence. 

Give us the top five best dates you have ever had. 

My favorite date was my first date with my wife, Jasmine. We went to see a movie called “Unstoppable.” I think that date was special because I felt some type of way early on for her. While we were in the theatre I remember looking over at her and feeling something for her. I want to say it was love at first site but technically, it was not the first time I saw her. Looking at her in the theatre, something spoke to me in that moment and I realized that she was not just some random girl that I was on a date with; that has always stood out to me. I don’t have many dates to reflect on because my first marriage was pretty early on.  

What about the worst/funniest date you have had?

The funniest date is the same date actually. I accidentally left my wallet at home and I thought I had it in the arm rest of my car. It was really embarrassing. I didn’t want her to think I was a bum or I was trying to play her. So I told her we could just reschedule and I would take her home but she was really cool about it. She said, “I got this date and you can pay for the next one.” That’s probably why I married her (lol). 

You have started your series “Motivational Mondays” on Instagram? I actually check it out myself. What inspired you to do this?

I believe that I have discovered what I am meant to do and that is to inspire people. Outside of entertainment, I feel as though I have gone through my journey in life with the help of inspirational people such as Les Brown, Myles Munroe and my mentor, Pastor Hosea Collins. These men have given me tools to help me through life, whether that be through my career, relationships, etc. I think sometimes perspective is the determining factor of how we decided to respond to life’s situations. My hope is that I can give the next person the tools they need to help them push through the trials and tribulations that they might be going through. 

Is there anything that you would like to add?

I just want to say thank you for the opportunity of giving me a platform to tell my story. Also, if anyone hasn’t seen my special “Chicago, I’m Home,” its streaming on Amazon Prime and is available for purchase on iTunes and Google Play.

Thank you so much.

Make sure you check out “Chicago I’m Home” and follow Barry Brewer on Twitter @barrybrewerjr and Instagram @barrybrewerjr!


—————————————————————————————————————————————-Author, blogger Kai Nicole has emerged as an exciting and unique voice on dating and relationships. A graduate of Harvard University and Howard University School of Law, Kai’s professional experiences encompass diverse fields including legal, tech, and entertainment. She is a mother, world traveler, foodie, and lifestyle enthusiast. Be sure to check her personal blog at! And, don’t forget to buy the best dating book for women, Date Like A Woman!

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