What do you struggle with most while on the road?

The hardest thing is trying to keep your voice. For example, we have a show tonight and Lollapalooza tomorrow and all of my friends are in town, a lot of them are performing and I want to go party and have some fun but unfortunately you can’t. You can’t have dairy, you can’t have spicy food, you can’t have coffee, you can’t have anything acidic. You can’t drink and I like a drink here and there. And you gotta sleep. I think from the outside it looks so cool and crazy and fun but in reality you have a strict schedule. 

At just 23 you wrote the hook to Eminem and Rihanna’s triple platinum smash “The Monster” but some may not know you originally wrote the song for your own album while going through a challenging time and suffering from depression. 

It’s still kind of crazy to me. I was [the lead singer] in a band formed by Pete Wentz called Black Cards, which led me to get signed to Island Def Jam [under Pete Wentz’ Decaydance label]. It was my dream to be signed.  The day I found out I literally just got up and left Italian class and was like, “Fuck this,” and never went back to school. So we did the whole band thing and I learned a lot, met a lot of people and traveled the world but it didn’t work out and they dropped the group. I was really bummed. I remember sitting at home for hours and hours just writing and nobody would pick up my calls, even my old managers and people at the record label, everyone disappeared from my life so it was hard. You think you have all of these people around you who act like they love you but you have to learn the difference between who your friends are and who the industry people are. I went on the internet one day and I was Googling sad quotes—I Google quotes to make myself feel better [Laughs]—and there was one quote that really hit me that said, “We stop looking for the monsters under our beds when we realize they are inside of us,” and that inspired me to write the song.

Could you feel you were onto a hit?

I jotted it down and I remember I took the ferry then the 5 train all the way up to 125th in Harlem and I walked to the studio, like any regular day. It was me and my friends and I told them the idea I had and wrote the song. When we left we felt really good but you never think it’s going to lead into something so big. [I had a gut feeling Eminem would relate to the spirit of the lyric] so it was sent over to the Shady camp and we heard that Em loved it and wanted the files then they disappeared for like a year. Do you know how much that messes with you? But things take so much time and patience. I know it’s terrible but when you get knocked down so many times you start thinking that way; you start telling yourself, “Okay, this isn’t going to work out because everything else fell through so this is probably going to fall through too.” We hadn’t heard from him so I just thought, “It is what it is,” and let it be because I had been constantly calling my manager like, “What’s going on?” and it was giving me such bad anxiety.

After a year of waiting how did you hear the good news?

One day Rihanna tweeted something that said, “I just recorded a #monster hook for one of my favorite artists,” and I just knew! But I still didn’t really think it could really be possible … I remember being in the studio with The Monsters and the Strangerz, who are producing my up-and-coming album, and they were like, “Yo B, check out Eminem’s Facebook right now. They put up the [“The Marshall Mathers LP 2″] track listing, look at number 12.” I couldn’t believe it.

Have you been able to take it all in?

I still actually haven’t. It came and went so fast. I still think, “Did that really happen?” Even with The Monster Tour, it’s weird that an idea that I came up with is now the name of a tour and it’s all stemming from that energy, the energy of something that came from deep within me and spoke to me and now it’s this thing that hopefully helps other people. It’s just crazy to me because I still remember being so bummed, dying to get anybody on the phone. I would call publishers and try to get in the studio with anybody that I could and nobody believed in me at the time. Everyone jokes like, “Oh, did those publishing royalties come in?” but to me money is nothing compared to that feeling.

Will you see Eminem this weekend at Lollapalooza?

I will. The funny thing is, I’ve never met him. After I wrote the song I was shopping it for my debut album but then the producer played it for someone at Shady and it all just kind of happened. It is kind of weird the way the whole process happens though because people think I talk to Eminem and actually I just wrote a song. He knows my voice but he probably doesn’t even know what I look like or that I exist.

Your first single “I Can’t Stop Drinking About You” also came from a vulnerable time in your life. Did the song lyric literally come to you while you were out mourning a breakup? 

Yeah. I don’t want to talk about the guy, I don’t want to give him that glory but I’ll share the actual story behind that song. I had gone through a tough time with this guy. He broke up with his ex for a year and wanted to get back together with her but was also in love with me and was playing mind games. He was like, “I want to be with you but I love her. What if I’m meant to be with her? But then again what if I’m meant to be with you?” You know how it goes, the games, so I went out to this place in New York called Johnny Utah’s and drank that night. Drank a lot. [Laughs] Johnny Utah’s looks like a Western restaurant and you can ride a bull in the middle of the dance floor so I was on the bull and they were giving me free shots but I was thinking about that guy all night. I couldn’t get him off my mind. Then he called me and said, “I need to talk. I shouldn’t have told you that. I think you’re the one.” I’m like, “There is no I ‘think’. If you love somebody, you just know. I don’t want to be an option.” I was like, “Fuck you. I’m sitting here at Johnny Utah’s and I’m fucking drinking about you, mother fucker,” and wrote the song about him. I wrote a lot of my album about him.

But the song goes deeper than just drinking your sorrows away?

Yeah it’s not about the drinking part of it, I think it’s more about what it’s saying and the way it makes you feel. When you feel like you’re losing a part of yourself and you’re at that moment where you’re about to go buy the Häagen-Dazs and chocolates. So it’s not necessarily about going to get shit-faced it’s really trying to say, “You really messed me up and I’m really hurting right now.”

What is something you must do pre-show?

I have to have throat coat tea, I have to do my vocal lessons, I have to work out and then I tell everybody to not fucking talk to me for an hour before because I talk a lot if you didn’t notice. [Laughs]

What does a typical work out consist of for you?

I love kickboxing and SoulCycle … I actually get teary-eyed [in SoulCycle], I’m not even joking. They have loud music playing, lights going and you feel like you’re in a disco. You’re in a room filled with 50 sweaty people and then they’ll say something super motivational about whatever was holding you back that week. Of course everyone has something, we all have our issues and then you hear, “Just push through. Just breathe.” It makes you emotional.

Ideal first date?

I like chill stuff. I don’t like movies, I don’t need to go to a five-star restaurant. Just sitting at a park on a bench with a really yummy dessert from takeout [would be nice]. I like anywhere relaxing without a lot of people around because I hate when you go to a restaurant on a first date where at the next table there is somebody right next to you who you know is totally listening. I went on a date the other day and it was the best date ever, we literally just drove around Hollywood in his car, got food and scratched lottery tickets.

Has dating changed as you become more known in the public eye and dubbed one of 2014’s breakout vocal vixons?

Kinda. Everybody gets a little scared, right? You just want somebody to like you for who you really are. I try to meet people through friends. Honestly, I have a hard time dating. Before the date I recently went on I hadn’t been on a date in two years. I don’t like dating people in the music business. I tried that and it’s hard. I’d be getting text messages, “Hey, I’m in Canada now,” and I’m like, “Well, I’m in Chicago…” So let’s just make this clear, my favorite dates are driving around scratching lottery tickets! And a really good red velvet cupcake and a little cup of coffee. And walking along the beach.

Favorite clothing stores?

I’m from New York so there is this store called Patricia Field. I like the weird shops that people don’t really go to that also have up-and-coming designers that nobody knows about yet. I have a lot of my friends design a lot of my clothes. My friend made this. I go to Topshop. I like AllSaints. I’m a little bit more rocker-chic. I’m into grunge couture.

If you could have a drink with anyone, who would it be?

Chris Martin … I’d want to just pick his mind and bat my eyelashes.

KIRSTEN MICCOLI / A DRINK WITH at The Grill