Destin Conrad (stylized in all-caps) came home hungry, prepared to perform for a packed house at St. Petersburg last Saturday. The day after, he indulged in his mom’s cooking.

“My mom is gonna cook so much food for me and my team,” Conrad told Creative Loafing Tampa Bay via Zoom the day before his Jannus Live show. “She always does like the after-show catering whenever I do hometown shows.”

The 25-year-old Tampa-born R&B singer has had quite a year. After releasing his debut album Love on Digital—an homage to the music of the new millennium—and launching a world tour under its name, he followed up just three months later with Whimsy (stylized “wHIMSY”), an alt-jazz album that debuted at No. 3 on Billboard’s Contemporary Jazz Albums chart.

Conrad filled the venue with the same variety of incredibly fashionable, glistening, brown-skinned R&B lovers—and its upper terrace with his close family and friends—over a year ago during his “Submissive” tour. Now he’s back with a new set, fresh stage design, and a new live musical direction—interpolating his discography with early-2000s R&B hits—but with the same hunger for music and showmanship he’s carried since he first left.

This time around, Conrad brought R&B singer and frequent collaborator Mack Keane, who opened the show. Singer-songwriter Ambré also made a surprise appearance.

During a 20-minute Q&A, Conrad discussed his two new albums, growth points from his previous tour, and growing up in the Bay. 

Since you’ve started your tour, how are you feeling so far, seeing the response to your album up close and personal?

Oh, it’s amazing. I’m feeling so good. I feel like the first couple of shows were a little rocky, but we’re kind of in the swing of it now. I played Houston and it was the best show so far. I just feel like we kind of locked it in, like we’re getting the hang of it and it’s becoming more muscle memory.

I feel like the first couple of shows—they were good—it just kind of felt like dress rehearsals. But I’m excited for these next couple of shows to happen so I can really exercise this muscle. 

This tour does differ from your previous one because you have a bigger band—a drummer and a keyboardist. So when it came to arranging your set list and arranging live versions of your songs, what did that look like compared to the last tour?

It was way more fun because I just got more opinions from other musicians that I trusted. Whereas I feel like my other tour was kind of just me. But you kind of have to crawl before you walk in the touring world. But yeah, it’s been way more fun. I also had a musical director, which was amazing. Shout out to him, he helped me put together this show so well and I’m so glad I had somebody to bounce off of. It was a really fun show to put together—the most fun I’ve had putting a show together.

What else differs from your previous tour?

The stage design. I have cool curtains and a cool rug and carpet. We got some cool drum bass heads that say “Love on Digital.” That’s also something I feel like adds an element and makes it more of a fun show to look at. It’s very reminiscent of my last tour, it’s just a step up and in a lot of creative ways.

You’re from Tampa and a lot is coming out of Tampa. We heard it from Doechii at the Grammys. So what was it like growing up here?  How did you get your start?

My first memories ever, really, were in Tampa with music: Like going to church and singing at church and being in choir. My aunt was an evangelist, so she would have me do all the cool church events. We had church boat rides and I would go and sing and they’d give me $100. 

Those are my first like early memories of knowing that I could actually make music a job. 

Tampa’s everything. I love being from Tampa. I feel like it’s a very underrated place and there’s a lot of culture there. It’s kind of untapped, but I’m excited for it to become more of like a pinpoint place in Florida. Also, because Doechii is putting it on the map as well. I feel it’s really just us right now, lowkey. I’m sure there are more artists from Tampa, but like, she’s definitely trying to pioneer, for sure, for the city. It’s a beautiful city.

I went to elementary school in Ybor City, to a school called Philip Shore. It was a magnet school. Also, where I would sing as well—not as organized as the church stuff—but in my after-school programs. Just a lot of core memories and like early memories with music in Tampa. 

Two albums in one year. That’s a lot. How did you go about balancing the two? Did you make them simultaneously? Or did you make one first and the other one second? 

I made Love on Digital first, and that one took me about a year and some change to make. I really thought about it, it was something that I put a lot of thought into. And then I made Whimsy within a span of like two weeks. I had the first two songs, “Whip” and “Wash U Away” (stylized “wHIP” and “wASH U AWAY”), but they weren’t jazz-focused. We redid them and reworked them and then everything else I made within the span of two weeks and it was the most fun two weeks ever. It was so fun. It was such a creatively free thing that I did and I’m so glad I did it. I didn’t know I was gonna do that when I made Love on Digital, but it just kind of happened that way and I’m glad it did. I’m so glad that my fans are receiving it because that’s something I thought about. I didn’t think people would receive it. I just was overthinking, but I’m very glad I put it out.

A lot of your previous EPs have jazz influences in them. So has it always been something you’ve been interested in exploring?

When I moved to California, in high school, my freshman year of high school, I was in jazz choir and I learned a lot about jazz music. I was studying jazz music a lot and I became a student of the genre. My jazz teacher also was amazing. Shout out to him, Mr. O, he was a cool guy and he definitely put me on to a lot. So I kind of always had that jazz muscle. I knew I wanted to make jazz music. There are like influences, obviously, just naturally within my previous EPs. But yeah, I knew I did. I just didn’t know I would make it a couple of months after putting on my debut album.

And how was making your debut album? Did you overthink the same way you did with Whimsy?

I didn’t overthink. I did think, though; I thought a lot. With Whimsy I kind of just acted. I did the first thing that came to mind. But like Love on Digital, I did put more thought into it because I wanted pockets; I wanted to make certain songs that felt like this, or like I needed a song that could play in a club, just like little things like that I thought about. It was also the most fun, as well. It was a really fun album to make. I wanted a lot of the songs to be fun. I didn’t want it to be super sad. Even though there are a couple of introspective songs on there, the intention wasn’t for it to be sad at all. I really just wanted to make a fun album. I knew I was putting it out around the summer and it was just something that I wanted to be really fun and lighthearted.

Speaking of fun, your charisma really does shine through in all of your bodies of work. And that probably does come from your background. You’re Jamaican and Jamaicans are naturally very charismatic, you grew up on Vine. And so I’m curious to know, are you intent on having that playfulness in your songs? Or is it something that happens naturally?

I feel like it’s something that happens naturally. I feel like my friends would say I’m a fun time. And I think naturally, it just shines out within my music for sure.

What was your inspiration when crafting these two albums? What were some things that you were listening to often?

For Love on Digital,  it was all the digital era of R&B. It was Justified by Justin Timberlake. It was Full Moon by Brandy. It was Timbaland-produced beats. Lots of just digital sounds—music and things that we made when we got the new software.

Is that why it’s called Love on Digital?

Yes, it was my ode to the digital era of R&B.

And then for Whimsy, I listened to a lot of jazz of course, I listened to a lot of Miles Davis, Chet Baker, Vanisha Gould was on the album. She’s one of my favorite, favorite, favorite jazz singers. I’m obsessed with her. And I’m so glad that she was down to be on my album. I listened to a lot of her albums. She has an album called Life’s a Gig. I played that to the ground. 

And why did your name your album  Whimsy?

I looked up the definition of “whimsical”—things that are off the cuff and  not expected. I feel like that’s what jazz music is to me. Like, you don’t expect it, you don’t see the changes coming. It’s very like, “Oh, that’s what y’all chose to do?” That’s why I called it Whimsy because that’s what it is. 

What are you most excited about coming back to your hometown?

To eat. 

My mom is gonna cook. My mom is gonna cook so much food for me and my team. She always does like the after-show catering whenever I do hometown shows. So it’s gonna be so great to just see my mom and hug my mom. I’m gonna stay an extra day, actually, for my day off and just hang out with her. Take her to go try some food that she probably won’t like. Yeah, just spend time with my family, my sister, and my nephew.

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This article appears in Sept. 25 – Oct. 1, 2025.