Kendra G. grew up with a love of media that was inspired, in part, by Oprah Winfrey. After graduating from Hampton University in the early aughts, she took up her first commercial radio job in her home state of Connecticut. Since then, she has worked as an on-air and TV host in a variety of major media markets from Atlanta to Chicago, doing what she loved. Then came the 2020 COVID-19 pandemic, which shifted the trajectory of her career.
A breakup, subsequent isolation, and inspiration from D-Nice’s Club Quarantine led her to hop on her own Instagram Live one day and interview single people who were looking for connection and love. That’s how her digital series Singles was born. It blew up, led to a dating app, a card game, and eventually got the attention of producers at OWN. Next up for Kendra G. is playing matchmaker on OWN’s digital series titled Dating Download, which launches on July 29th. Her Agenda caught up with the media maven to chat about her journey thus far, the full-circle dream of working with Oprah, how being single isn’t the end of the world, why dating should be fun, and more.
Her Agenda: OWN describes Dating Download as being part of its strategy to deliver relatable, empowering content that highlights the brilliance, beauty, and boldness of women. I thought that was beautiful, especially now, when women’s voices are more important than ever, especially Black women. Can you elaborate on what it means to be part of that?
Kendra G.: It’s a dream come true. Every media woman can only aspire to have a career like the Queen of Media, Oprah. I call her “Mama O.” She’s literally God in the media world to me, for a lot of reasons. Without the city of Chicago, her show wouldn’t have been successful. Chicago embraced her, and that’s my same story. My media career really thrived in the city of Chicago that accepted me. I went from being the host of a show to the owner of a show. That was the lesson I learned from [Oprah] from starting this journey in the Singles space and creating my own show, which I own, creating my own dating app, which I own, and being the face of it. I learned that from her. So for God to align me to have a show on her series, I didn’t even dream that big, so I feel very fortunate. You couldn’t write a better story.
Her Agenda: And your Singles series on live, which springboarded this, started during COVID too! How did that unfold?
Kendra G.: I’m a journalist at heart, so for most of my career, I interviewed celebrities. Then, starting in COVID, my whole platform, my whole empire, I like to call it, the product of a breakup. I was in a relationship, and we broke up, and I couldn’t quarantine with anybody else. I was hosting the morning show in Chicago at the time during the shutdown. We were no longer allowed to go to work with each other. So, when my then-boyfriend and I broke up, I was single-single, and I had a dog, and I couldn’t be around anybody else, and D-Nice was connecting us via music at the time on IG Live because we were all trying to figure out this world. And I was like, ‘Okay, well, if I feel this way single, I’m quite sure other people feel this way single, so let me just go on Instagram Live and connect with other single people,’ and literally that one night, I knew I changed my life forever because with my media background, I knew I had gold.
It literally began from that one night with an iPhone and a ring light. It’s an honor to be a voice. It’s an honor to be selected, and I take it very seriously, and I really do want to encourage all people, but obviously I have more women followers than anything, to just know that as you’re on this quest, you’re looking for love to spill over, you already have all the love that you that you desire and that is required, and a person’s going to love you the way that you love you. So, with this single season, don’t negate it, don’t be sad, live your best life. I’m having the best life ever as a single person. For six years, I’ve been in a relationship. I’ve been single; I’ve been in a relationship. I’ve been single this year in particular. It was a very clear decision. I decided to be single this year because of this opportunity. I signed the contract back in February, and I didn’t want anything to mess it up. I support relationships, but the wrong connection to the wrong human being can ruin your life. So, single seasons are necessary. It is necessary to focus on yourself and pour all into yourself so that what you would give to another person is in its best form. I just love showing that you could be single and happy. I tell my age all the time because there’s this narrative that when you get to my age and you’re not married or you don’t have kids, you’re miserable. But baby, I don’t club hop. I country hop. I’m gonna be in Antigua next week.
Her Agenda:Yes! There’s a wedding coming up for you in Antigua. That was the product of your matchmaking, right?
Kendra G.: This year, in particular, we have four weddings. We had a wedding in May, we have our second wedding in Antigua next week, and then we have another wedding in Chicago in August. So with the dating app alone, we have four weddings in 2026.
Her Agenda: I’m glad you said this about the weddings, but also about being single, because you also seem to trigger some people, especially men. I’m seeing people online mainly come for your singleness or to question your matchmaking.
Kendra G.: What I’m doing is breaking the illusion that life is supposed to be over. You’re not married, you don’t have kids, you’re supposed to be miserable, crying, and sad because you don’t have those things, and it’s literally the opposite. I’m more successful than I’ve ever been in life in all courses, even in my personal life. Life is getting better; it’s just my reality. I always wanted to live in California. I live in California. I wake up every day, like I cannot believe this is for real. Like, this really happened for me. So, I ruffle the feathers of those who can’t stand the fact that I’m a Black woman and I’m doing well in life without a man, and I’m doing better than you thought I would. I’m not supposed to live this amazing life. I’m not supposed to live in Beverly Hills. That’s what the narrative is stating, and I’m here to blow that whole shit up, and it’s only gonna get better
Her Agenda: Let’s talk about Dating Download. Is it an extension of Singles, or how will it be different?
Kendra G.: What we do with Dating Download is, we took ten women, and we did the best that we could to find them the guy that they described. Now, maybe we got them via aesthetics, maybe we got them via character, but we did our best to try to match what the woman said she wanted. She goes on this blind date, and then after the blind date, is this guy the one? Do you want date number two? Do you want to download the date, or do you want to delete the date? And what’s interesting about it is sometimes you might say you want something on paper, but when you get it in reality, do you still want it? And what if what you want on paper doesn’t want you back? So that’s what Dating Download is.
Her Agenda:Finally, what do you hope people take away from the Dating Download?
Kendra G.: I want to bring fun back into dating. I think a lot of women are very serious. We don’t waste any time. It’s like, ‘I want to meet my husband on day one,’ and it doesn’t really always work that way. And I think if we make it a little simpler, and just enjoy it, enjoy the date, like, you go on the date, and maybe it’s a date that you never see this person again, or maybe it’s the first of many, but whatever it is, enjoy that date and that moment for what it is, and you know what comes next, right? So, what I hope people get from the Dating Download is that maybe you’ll see yourself and some of the women, and maybe you’ll learn about how we have to date in this new world that we’re in, but more importantly, just have fun again, be happy in your own life. If you meet a person, they’re adding to the happiness that you’ve already created, and that’s what I hope. I hope you’re entertained by it, and maybe you’ll see yourself in season two.
[Editor’s note: This article has been edited for length and clarity.]
