On a Date with the Rapper Who Says Not to Date Rappers

South Side rapper Ausar’s excellent debut album, I NOW KNOW., has been years in the making, and covers a range of musical and emotional terrain. But at one point, the tracklisting offers simple (albeit tongue-in-cheek) advice: “DON’T DATE RAPPERS.” 

So after catching the album’s launch party at The Promontory in Hyde Park, curator, artist, and Weekly contributor Luz Magdaleno Flores had to invite the rapper on a “date.” 

The two met at Ausar’s favorite date location—Lurie Garden in Millennium Park—to discuss vulnerability and honesty in all things love and music. 

The interview has been edited for length and clarity. 

Luz Magdaleno Flores: How does it feel to put out your first album? What feedback have you gotten so far?

Ausar: What I feel most is relief. Like, we’ve been working on putting it out for about six years now, so to finally be on the other side feels incredible. And the response that we’ve been getting has been even more incredible—to have this much attention on something that I created with my friends with no label. It’s very affirming, in a lot of ways, that we are on the path that God has for us.

What’s your favorite song on the album?

It changes every day. Today, I’m feeling “Ghosted.” The beat on that [song] is incredible—and that was a really special song, because that’s the only song on the project that I didn’t write. I freestyled that song. And that was a different process for me, I don’t usually do that. It was one of my more vulnerable songs. In a lot of my music, prior to this album, I didn’t really express much of what goes on personally with me, in my love life or in my relationships in general. And now we kind of got me out of the box. So I really enjoyed it.

Let’s talk about that step towards vulnerability. I think that a lot of us can relate to the album, because you’re very honest. And you’ve opened up that door to confessional sad boy, honest boy vibes that remind me of Brent Faiyaz or Drake. It’s almost like poetry—or like confessions, you know?

For sure, I would agree. I think that was a hard step for me, and I think that’s what took me so long to make an album. Because when you’re not speaking from a place of honesty, or complete transparency, it’s hard to make music that people can relate to, because you’re not being your authentic self. 

For a long time I was holding myself back, I was just like, I don’t want to talk about this. Because if this person hears it, how are they gonna feel? Or how are people going to view me after they hear these versions of me that I don’t usually expose. And I finally made the conscious decision to go with my truth. I have to live in that. It’s not like I don’t live and grow and change as time goes on. But this is where I was in this part of my life. 

So talk to me about your writing process. How did these songs come to you? You’ve mentioned that you scratched a full project or album before this.

[It’s a project] that we had been working on for like, five years! And it’s due to what I was just telling you. It just didn’t tell my story anymore. I was craving some change. I was craving new things. And I went out to do a session in LA at the end of 2021. It was November and I recorded a song called “LIST” that’s on the album. And that was the first time we officially made a song for the album. And that was different. The beginning. The first four bars of that I freestyled… and after doing that, I kept writing. It was so different from everything I had made at that time. 

I hit Ro [Moore] up—my producer, engineer, executive producer of the album—and I was just like, I want to do more of this, like different things. And they all supported me. So my writing process from that point forward was literally just coming into the studio and trying new things. I had an idea of what I knew I wanted the project to be about. I wanted to tell a story. But I was like, okay, let me just chip away at bits and pieces of what I want the story to be.

I want to talk a little bit about your background in gospel. You grew up in a very Christian household, right?

Yeah. I think my art reflects who I am, right? The gospel, my own personal faith, and how I choose to go about my walk with God. That shines through in everything I do. Since I was born and raised in a church, and that was my first introduction to music, everything can be very grandiose at times—like you’re gonna hear organs, you’re gonna hear pianos, you’re gonna hear chords in chord structures that are not really pop, you know? I think that we’ve done an amazing job of making that digestible for everyone. But it’s very much pulled from gospel.

Where in the South Side do you rep?

The Auburn Gresham neighborhood. Over on 95th and Eggleston, right next to Trinity Church. And South Shore. I was there from the time I was like, ten to eighteen. Right across the street from South Shore High School.

Are there choir groups from the South Side that you would like to shout out?

Absolutely. [Selah] St. Sabina Youth Choir, and Sam Williams. They were a part of a joint on the album called “poster CHILD” and that was a super cool experience, having a lot of kids pull up and be excited. I was super excited too. That moment in the studio, I’d never seen a choir be recorded before. That was an experience in itself.

So, talk to me about those sounds you grew up with.

My first introduction to rap music came when my mother got married. One of my oldest brother’s name is Nick. Nick is the one who got me rapping. And I remember the earliest introductions I had were like, Kanye West, Lupe Fiasco, and Common—who was my favorite rapper, because everything he was describing, the stuff that was around, I was just like, “I know exactly what you’re talking about!” And that was my launching pad. Another musical influence was my older cousin, Nene, who is a poet, and she was in love with Lauryn Hill. So I would listen to Ms. Lauryn Hill and India.Arie all the time because of her. But my dad gave me the first .mp3s that I ever had, and he uploaded music that he was listening to. It was, like, De La Soul and D’Angelo. Those foundational pieces all came from my family. 

Talk to me about “DON’T DATE RAPPERS.” and how that idea came to life. What’s the backstory? 

So the first half of “DON’T DATE RAPPERS.” came from like, a couple of instances where some of the women who were interested in me, I genuinely felt like only were interested in me because of what I do. This wasn’t off a hunch, this is off of, “I’m watching who else you keep yourself in relation to, and who else that you’ve dated in the past, and who you’re even currently talking to while we’re talking,” and it just felt very superficial. And I felt like I had to get it off my chest. So the first half of “DON’T DATE RAPPERS.” is me just kind of voicing that. The second half of “DON’T DATE RAPPERS.”—and I’m so happy to talk about it now that it’s out—is more of an introspective look. Me looking back at a lot of my dating history, and realizing that I was the problem in most of those situations, whether it was direct or indirect. I am talking about a lot of the issues that I have, when dating. And a lot of the homies have also shared that same sentiment, whether it be making time for someone or having somebody who understands the passion and the drive you have behind what it is you do, and understanding some of the decisions you’re gonna make as it pertains to that. A lot of times, creative art comes first, and everything else is secondary. And that comes with a whole lot of problems in itself. 

I asked some of the girls at your record release and your homies wearing your hat that says “Don’t Date Rappers: an emotional warning” what their thoughts were on the message and a lot of them said, “Oh, it’s a good time. It’s not a long time.” Some of the girls were like, “I’m wearing the hat because I love AJ, he’s such a sweetheart and I’m supporting him.” But you’re wearing a hat that’s literally saying “Hey, don’t date these troubled men,” and they just laughed it off. I was having drinks with some of my friends yesterday and I asked them too,”Hey, would you date a rapper?” And they were like, “Honestly, yeah,” because they wanted to have your attention. You know what I mean? I kinda want to hear your two cents on that. 

I think everybody—because of how I was raised and my own personal belief system—everybody deserves somebody. So it’s unfortunate that a lot of people do come into dating rapper dynamics, [with the] understanding that you’re probably not the only one. Because in a lot of instances, you’re not. I think when I was younger, I had a very hard time coming to terms with commitment, just being very real. I had so much going on. I think now as I get older—and I was just talking to a homie about this yesterday—I’m valuing genuine connection. I’m valuing being able to give somebody my all and really invest in them. And so for me, I am for sure, looking for one person. And I think some of my homies also feel the same way. A lot of my music friend group is made up of men in relationships, and some of them are married and have kids and have already started that journey for the rest of their life. And I think that’s so cool. And in a lot of ways, I look at that as an example for me. I think it comes with a lot of discipline, because when you’re in as many people’s faces as you are as an entertainer, people are going to be interested, people are going to press those boundaries. But as long as you have that self-discipline, I think it’s very possible.

Who’s the girl on the record that leaves you a voicemail saying to answer your phone?

That’s actually a homie of mine. That is the only voicemail on the album that is not a real voicemail. I was okay with leaving a lot of voicemails on there without people’s consent for them to hear it because I thought it was gonna be like a nice surprise. 

You didn’t want to get sued?

I didn’t want to get sued. You also just have to be cognizant, like there does come a responsibility with how you put your art out, right? And my intent is never to hurt anybody. So I can get mine out without being malicious in my approach. 

Is there a difference between AJ and Ausar? And what are those differences?

I try to make sure that there is not. But inevitably there is. I try to show up as my authentic self in any room that I’m in. I do think there is a difference, though, in terms of how people view me as an artist and how people who personally know me view me. I think there’s a mystique and a shroud around, like me as the artist. Once you meet me and get to know me, you realize I’m the same person everywhere.

I see it in your eyes, like you still have hope for true love.

Oh, absolutely, man.

Is there a spot in the South Side that holds a special place in your heart?

South Shore High School is one spot because of their basketball court that they have outside. I was there every single day when I could go during the summer. That was my safe haven. Like, I was at that court every day. I mean, Michigan Ave as well. I know it’s not the South Side but this is, once again, a very pivotal area to my upbringing, because you know, when you were shorties, you will wait the whole week to get to the weekend and come downtown and just walk the strip by way of the Jeffrey Jump, the J14, which was my limousine to downtown. 

You sound like you played a lot of basketball.

A whole lot of basketball. I love basketball—like up to the current day, when I can’t write and I’m not having the greatest day, I go shoot around. That’s my thing.

So you play games. You’re a rapper. You’re a Gemini. And a church boy. You must be trouble.

I don’t think so. I’m not that bad. 

Visit www.ausarmusic.com for more on Ausar. 

Luz Magdaleno Flores (she/her) is a Mexican Chicana artist, poet, journalist, and fotógrafa based in Chicago by way of Oxnard, California, also known as DJ Light of Your Vida.