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"I'm a true hopeless romantic and I feel like you have to not be afraid of love," says 29-year-old singer Jhené Aiko.

Aiko, an amorous soul who relishes the concept of love and the fruits that it bears, has admittedly found herself before on the short end of the stick in romance. After losing her brother, Miyagi, in 2012 to cancer, Aiko feverishly searched for a man who reminded her of her close friend. With each romantic encounter, she sought humor and soulful conversations as nourishment. While she looked for fulfillment in the love department, on the music front, she bloomed into one of R&B's premier songstresses with her 2014 album, Souled Out.

Through records like "Lyin' King," "W.A.Y.S." and "Spotless Mind," Aiko's precociousness as a songwriter had listeners enthralled. Still, she felt empty. With the loss of her brother weighing heavy on her spirit, Aiko ventured to Hawaii to seek liberation. Her journey sparked her creativity and enabled her to splash drops of candor onto the canvas like never before. The end result? Her latest album, Trip.

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Watch Jhene Aiko's Emotional Journey in Her New Short Film 'Trip'

Laced with 22 tracks, Trip shreds the public's perception of Aiko and allows everyone to walk into the life of Penny, a nickname she was given by her great-grandfather when she was a child. For the first time, Aiko gives listeners a front row seat and allows them to watch her undergo a whirlwind of emotions, including love, pain, depression and, ultimately, triumph. Billboard spoke with Aiko about her most honest work yet in Trip, her relationship with her late brother Miyagi, her evolution as a mother and why Big Sean is the love of her life.

Billboard: Describe Jhené now versus Jhené when Souled Out came out in 2014.

Jhené Aiko: Well, I'm almost 30, so that makes a big difference. I'll be 30 in March. I would say I'm more aware. More aware, more myself. I know I feel like you got my mission statement [at our listening session] where I talked about being Penny -- which is the nickname that my great-grandfather gave me when I was four -- and I feel like that is really my true self. I felt like he looked at all of his great-grandkids and grandkids when they were born and just saw something in them and he gave us all a nickname. I just thought he, with his wisdom, always saw our true essence, you know what I mean? And I feel the Jhenè today is more of Penny. [She] is more true, honest and unafraid.

In your mission statement, you also dedicated the album to your brother. How would you have described your relationship with him before he passed?

Since he passed, every day I've dedicated to him. I grew up in a house where it was five of us. We have the same mom and dad. We grew up in tight quarters as well, so we shared everything and everyone was like two years apart. So there's that two years, two years, two years and my brother, Miyagi. He was two years older than me, so we're the last two of the five. We pretty much did everything together.

My older sisters were always together, and then [we had] another brother who would pretty much be doing his own thing. A lot of the time, it would be me and my brother or me and Miyagi because we were closest in age. So we went through middle school together and had a lot of the same friends. We were close. I always felt like he was more like my friend, you know what I mean? People in school would always be like, "You guys aren't twins?"

Throughout the album you were trying to find pieces of your brother through men that you've dated in the past. What traits were you trying to find in men that resembled your brother the most?

I would say a sense of humor. Me and my brother were always very, very silly and [had an] inappropriate sense of humor where you can't joke like that with anyone 'cause they might be like, "Really?" It could be offensive at times, but we're super, super friendly like that and we love South Park and that type of humor. So that was always important to me.

My mistake in comparing guys to my brother was that a sibling, especially an older brother younger sister type of relationship, there's no stronger bond than that. No man will compare to that, because there's certain things that we just are going to relate to each other because we're related. We have the same blood, so it was an unspoken bond. We could talk about things that I can't talk about with anyone else because they're not going to really, really get it. But with him, it was like, 100 percent I knew for a fact that he understood me.

Any crazy dream I had or any crazy idea or anything like that was something that I was looking for, because to me, that was the best male relationship I've ever had in my life, you know? And so, in a lover, those were the things I was looking for, and I still do. But I know I'm more aware and I know that my brother cannot be replaced, but I know that because I'm still here, that he is within me.

Those are the things that I have to tell myself every day and practice thinking in that way, because it's really easy to go back to really, really missing him and being sad about it. But there's so many things that I do and my daughter does and my siblings that remind me of him, so it's kind of just like he's still within all of us.

Trip is really a rollercoaster because you're falling in love, then you fall out of love and then you're depressed and then you come back to that sense of happiness. So for you as a songwriter, which stage or phase was the most difficult for you to write about?

Honestly, I've been writing since I was in elementary school, so that was always my way to express myself, whether it be a happy feeling or a sad feeling. And I found that when I was dealing with an unpleasant feeling, writing was really my No. 1 choice when it came to, "How can I get through this?" So now, as an adult, it's easy for me. It's easier for me to grip difficult emotions than the pleasant ones, you know?

Pleasant emotions are like, "Yeah I'm fine, so why do I need to write or why do I need to create?" 'Cause I like what's happening right now, but when I don't like what's happening then that's when I take myself to another world and write about it and release it. And as I get older and develop my craft even more, I found that I'm getting better at expressing myself in every way. Even in my relationships, I just feel like I'm getting better and better at it.

I know how to record myself, so it's easy for me to do that. But when it's other people in the studio, or I have to listen to it back with other people in the room, then it starts getting a little hard because I'm like, "Oh, shit. You're getting a real glimpse into my mind."

Vulnerability has never really been an issue for you. So with that being said, were you concerned about giving away too much of your personal life this time around? Because you went really deep on Trip.

Right. You know, no, I wasn't concerned. And even though it was even more vulnerable than I've ever been before, it's still not like, everything, you know what I mean? I have a large wealth of stories that I keep to myself just because some things you have to keep for yourself. You can't give it all away or you will just be a shell of a person. I think I do a great job at balancing things or thinking creatively about things.

Just being creative about stories or things that have happened to me instead of being like, "Oh, this is his name and he did this." Sometimes I am very descriptive and it's very, you know, real. Just word-for-word, all those things happened. Sometimes, I'll take a situation and just sort of be more creative with my vision and use my imagination a little more while describing a real situation. But I definitely have some things that only me and God know.

At certain points of the album, you said things like, "You're too real to be good," or, "Hope you are who you say you are." How have you managed to let your guard down in relationships despite being hurt in the past?

I'm a true hopeless romantic and I feel like you have to not be afraid of love. If there is a "one" for us, just one person, one soulmate, whatever, then you're not going to get it your first try or your second try or even your third try. So I won't let one bad relationship ruin my chance at finding my true partner. I'm not a person that holds grudges, either. I just live in the moment. It's easy for me to just be trusting of a new person, which sometimes is a fault, you know?

I always tell people when I lost my brother that was the biggest heartbreak, but it also taught me about life and death. But as far as a relationship, like a guy that's not my sibling or not my child, nothing is gonna hurt me more than what I've already been through. So if they hurt me, that's their fault. I know I'm a good person and I'm a true hopeless romantic. I'm a loyal, loving person and I just look at it like that. If you're going to do me wrong, then you're going to have to deal with the karma for that.

You have John Mayer on the guitar for two songs on the album. How did you and John connect?

There were a few people [on my wishlist] and I got Brandy and John Mayer. When I got with John Mayer, he just really stands out. Basically, [I had] the flu and they're like, "Okay, he'll come to the studio today." I'm like, "Oh no, I feel horrible." But I wanted [the session] and was taking it. I kept getting up to go to the bathroom to blow my nose and stuff like that 'cause I didn't want to gross him out, but he was amazing.

He stayed for hours and hours just playing guitar riffs and singing little song ideas and stuff like that. He’ll record everything. We recorded everything and I just picked out a few guitar licks that I like and built a beat around them. I played him "New Balance,” which wasn't complete at the time, and he was like, "Oh, I love it. I want to try something on this song. Can we add a guitar to the end of that song when the beat switches up?" That was an amazing experience.

You have a song on your album with your daughter Namiko titled "Sing To Me.” How do you feel you've grown as a mother since your debut album?

I just feel like as a person, I really see the importance of family now more than ever. I’ve taken a lot of trips to escape. I read a lot of books from Thich Nhat Hanh. He's a Vietnamese monk and he talks a lot about finding that peace within yourself and finding that peace within your immediate family, because people so often try to tackle the world without tackling their own issues within their self and within their family.

These people who are protesting every day and are on Twitter, they are not trying to work out the issues with their mom, or their brother and sister, with their family. And you really have to take it one step at a time, 'cause that's where it all starts. If you have that foundation and you guys are all loving, you guys have a loving self, they are loving towards themselves and loving towards their family, you guys can move as a unit and be a force of love.

Then, you all can go out into the world. I feel like my daughter has taught me that in so many ways. She's getting older; she'll be nine in November. Just that, the innocence of a child, the optimism, is just so inspiring to me. Before, she would just cry about things, but now she's communicating to me like, "I don't want you to go here. I want you to stay," or, "I want to come with you, I'm scared because I miss you." Telling me stuff like that. We have a really good relationship. We're compatible.

Everyone isn't as compatible with their parents, but we're lucky because she's a Scorpio and I'm a Pisces and I feel like we are compatible on a friendship level, too. We really have open discussions and we're really growing up together. I just feel more responsible. I feel like she knows that I'm not perfect and I would never ever pretend with her, but she also sees that I work really hard. We're just open with each other.

Big Sean appears on two tracks. The first one is “Moments” and the second one is a TWENTY88 record titled “OLLA.” If you could describe your relationship with Sean in one song or album, outside of your collaborations, which song or album would you choose and why?

I would choose -- is it Common and Erykah Badu? [Singing] “Love of My Life." I feel like because I've never ever ever had a relationship where we were friends first. I'm the type of girl that if they're like, "You wanna be my girlfriend?" I'm like, "Yes." It's just like, "Okay, we're together we've known each other for a week and now we're exclusive and serious."

When I met Sean, if you looked in the dictionary for Jhené Aiko, it would be a picture of Sean. Basically, he is my type, but he knows. That's why when I was 16, I had a lot of boyfriends that were like, that fit, that look. I was dating people who I wasn't attracted to right off the top or whatever. So I ended up not having a type. But then when I met Sean, I had a boyfriend and he was showing interest in me, but I was like, I have a boyfriend. But we were friends, it was never, nothing disrespectful ever happened between me and Sean.

Then when I broke up with that boyfriend, he had a girlfriend. So it was, 'Okay, alright.'  We're still friends and we were forced to really, really get to know each other on a friendship level, you know what I mean? And to the point where he was even at my brother's funeral. We talk to each other on a friendship level throughout all of my relationship, just like, "How is this one thing, how are you doing?"

And obviously we worked together as well throughout our relationship. We did songs together. And then it just came to a point where it was like, "I'm single, you're single, we love each other." We actually already loved each other as people and then it was like, "Okay, let's just, you know, be together." So it was different because of that friendship. That comes first, we're friends before anything. We can bicker like a friendship.

If you're friends, when we're debating something, it doesn't turn into some crazy argument because we're actually friends. I have a big family. The friends that I have become family. I don't have a bunch of friends. I literally have like two friends outside of my blood relatives. Everyone else that I call a friend is literally related to me by blood. So Sean has become my family. I don't know what the future holds, but as far as my life goes right now, yeah, he's "L-O-M-L."

What are you hoping that your day one fans take away from this album?

Well, I hope that they take their time with it, No. 1. I hope that they really, really dive into it and just immerse themselves in it. Because like you said, it is a real trip and I feel like I definitely have a lot of fans that have been following me since I was younger who are my age now or even older and they really understand the concept of why, and they've been through losing someone and they've been through relationships that have been unpredictable and they have been through these things. And if anything, I would want those fans to just really just take in this whole map, the movie, the album and the poetry book and just be proud of how far I've come. Because I feel like I've really, with this M.A.P. [movie, album, poetry book], with this whole project I really gave my all, 150 percent. No distractions.

I was surrounded by only people that are loving and supportive. This is the first time that I can say that. The other projects I was doing, there were a few people that were definitely not around for the right reasons and were definitely using me, and stuff like that affected my projects, But this time around, everyone that I'm surrounded by has been nothing but helpful and supportive and I think it really reflects in the music and the album and the movie and the poetry book I made.

I have a lot of younger fans who have never lost someone close to them or haven't experienced a lot of relationships. To them, these are just songs. But for me, because this is a timeless piece of work, I feel like it's something that needs to be revisited. There's a song for everything. There's a poem for everything. I feel like the movie also touches on everything that the album and the poetry book touch on as well. So I feel like, I would just want them to have a better understanding of me.