Glamour: Have you always been an upbeat guy for the most part?

Andy: I've always been really happy, but losing my mom to breast cancer really grounded me. [Up until that point] I didn't get hit with anything pretty bad. I was just a happy guy, and if you were sad, I didn't understand why and would try to cheer you up. When I got hit with [my mom's diagnosis], it was like, "Whoa." It was a year of not being super happy and just being a quiet guy at the table. I think that really helped give me some depth for what my mission is musically. If I was going to sing these types of song, it helped to know [the pain].

A photo posted by Andy Grammer (@andygrammer) on May 10, 2015 at 7:16pm PDT

Glamour: How did you meet your wife?

Andy: At Cal State Northridge in the music program. She's an incredible songwriter. I didn't ask her out at first. We were kind of just acquaintances through music, but what got me is that when my mom passed away, I would do these voice notes called "Kathy Grams." That was my mom's name, so when people said, "Hey, I'm going through something. You said you'd write me a song," I'd write a quick little [song] about how you're going to be OK, things will work out, etc., and we'd call them "Kathy Grams." And so then Aijia [pronounced Asia] was looking over someone that was about to pass away, so the day she came over to write a "Kathy Gram," that's when we started to connect a bit.

Glamour: What made you know that this was the girl?

Andy: You know how you are when you're with your really good friends? Totally yourself? That's it. When you realize you have the relationship that "I am who I am when I'm with you," there you go. That doesn't mean you're not going to grow a lot together. You want to find someone you can change with, but you're OK to be who you are.

A photo posted by Andy Grammer (@andygrammer) on Jun 26, 2015 at 8:52am PDT

Glamour: You mentioned earlier that you were a virgin until you got married. I love that you were so honest about it. Why was that decision important to you?

Andy: I think we all know inherently what our faults are—like this year I'm trying no sugar. I can OD on sugar. So I inherently know that I'm capable of going way too far in that direction, [so] I'm not going to do that. I think there was something for me about breaking that seal that was like, "I really want to be a good guy, and I'm pretty sure that's one of my biggest vices, and I don't want to start that train." I don't want to be the dude that sleeps with you and then doesn't call. The problem is, as an artist, if you're not connected with who you are or honest with yourself, then your art sucks. That was a hard one for me. Again, it wasn't like perfect—in the song it's like, "A little bit of prayer, a little bit of porn." [Laughs] I was very honest!

Glamour: What's your most special fan encounter?

Andy: Fans have tattooed lyrics on their body, which is amazing. It just happened yesterday in fact. It was from the song "Sinner," so here this person that you don't know, but you meet for a short meet-and-great action and she has a lyric of mine tattooed.

Glamour: Do you have any tattoos?

Andy: I don't. I'm toying. There's a really cool Baha'i quote, and my music company is called Ladder Soul Music. There's a quote that says, "Music is the ladder to the soul," and I love that. So the idea of creating music and getting people ladders, I love that idea. So I'd get a cool ladder [tattoo]. I'm just afraid! Maybe I'll get a flash tattoo first to feel out what's right. [Laughs]