Editors Note: Since the inception of THE DROP, our goal has been to provide information on the music world with a “regular joe” approach. It’s been a pre-requisite for all the writers to take part. With that being said, I was still a little leery to post this interview. In all of the time that I’ve been asked to write and now oversee others writing – this is the most candid conversation about life and love I’ve ever read. So join Meridith and Jill around the table with Rosie Thomas and know that THE DROP loves you.

The Prologue: Rosie Thomas On Crapping Her Pants

Rosie Thomas’ worst Valentine’s Day ever? “Does going to a movie in 7th grade with Richard Cramb and crapping my pants qualify? does riding home in his parents car smelling like a dirty diaper count? If not, does the fact that the next day at school everyone wished me a ‘Crappy Valentines Day’ work?”

These days, I should take Rosie Thomas’ words with a huge spoon of Kosher Sea Salt. Especially when a subsequent email reveals the movie title:

“’Poetic Justice,’ maybe?”

After all, this is the same impish singer-songwriter-comedienne who convinced the folks at Pitchfork she was carrying Sufjan Stevens’ son. But this time around, there’s a contented glow in Ms. Rosie T’s eye. No, not that glow—the kind of glow belongs to a content woman.

Total cheese, perhaps, but it’s the glow of love. Well, love and stardom anyway. So, in honor of all things Cupid, The Drop brings you scoop on the love life, latest projects, and even a sneak peek into the real heart of Rosie Thomas.

What follows is a partial transcript (with notes) from our chat.

Chapter 1: On Moving On (or, The Broken Hearts Club)

In college, it was Rosie’s independent-woman ballad “Wedding Day” that hooked me. My friends and I would sing our hearts out as if we were in the car with her, ready to dance with those truck-drivin’ men, too. Rosie, we were sure, knew exactly what we’d been through and wrote those songs just for us.

So when The Drop had a chance to catch up with Rosie Thomas one night in the middle of a brief run of gigs opening for Over the Rhine last fall, it was a dream come true. After all, it’s not every day a girl gets a teary-eyed heart-to-heart with her favorite singer-songwriter, but that’s exactly what took place.

When I finally sit face to face with Rosie Thomas, there are deep circles under her eyes. The tour van got lost in the outskirts of DC. By the time they arrived, says Ms. T, the cramped Kia Rio reeked of “fart and breath.” Her brother called it “the worst experience of my life.”

The trio nearly ran out of time for sound check, performing it quickly in front of the waiting audience, and then launching into the 30 minute set. Afterward, Rosie had barely enough time scarfed down a plate of mac’n’cheese before our interview.

So there we were, sitting over a blue & white checked tabletop outside the music hall at the Birchmere, listening to Karin light up “I Don’t Wanna Waste Your Time” as Rosie takes a deep breath and a sip of her Diet Coke, and begins to share her heart.

“I ran into three girls in the bathroom and I’m brushing my teeth, you know, in the sink, and I thought, they must just think I’m such a loser,” she laughed. “But there’s part of me that’s like I’m so glad they get to see that part too because that’s really the truth.”

Fans of Rosie Thomas know that she wears her heart on her sleeve in her sweet, sometimes sad, lyrics. It’s that very transparency that makes her fans, well, her fans.

But that same transparency has seen a significant shift in the five years between 2002 When We Were Small, a heartbroken record that chronicles, in part, the heartbreak of her parents’ divorce (knowing this, the charming little family recordings interspersed in the songs become sad for their sheer innocence), and 2007’s These Friends of Mine, an album crafted with close friends as Rosie healed from the breakup of a significant personal relationship.

Chapter 2: On Finding Her Voice (With Her Eyes Closed)

Rosie Thomas once told Paste Magazine that “I’m a completely broken person and a weak person, and I admit those things in my songwriting. I make the choice to get over those fears, to push myself out on stage and just to perform whether I’m scared to death, whether I’m scared what people think.” These days, there’s a new perspective, though she still closes her eyes when she sings on stage:

“I caught a man yawning once, which is totally unacceptable–no, I don’t blame him, for the love of God, I mean it’s slow–and now I’m so afraid of making eye contact either cause I’ll start giggling or, Lord knows, maybe I’ll cry, I don’t know…maybe that’s why I feel braver and more free because I don’t think five years ago I really realized how much people need to sort of be tapped in that area of their lives, I think I was it was what I desired, sort like a projection isn’t it? Because I desire that from people, my closest friends–nothing thrills me more than when someone asks, How are you doing, Rosie? How are you really doing? Oh, god, that’s like flowers or notes or taking me out to dinner–it grabs me, I feel so noticed, I think, just me? Oh, well, yeah. You mean, not my music? No, no, just you. How are you doing? And then I’m like, where do I start? Thank you so much for asking. I don’t think I realize how much those songs would, could affect people–but thank God they do, I mean, if they didn’t I’d have to find a different outlet. I’d be a lunatic running around the world trying to gather people to talk about our hearts, you know?”

We talk about her recent switch from Sub Pop to Nettwerk, and I ask if she feels she has more artistic freedom now.

“[Sub Pop] was a great place to start because they really allowed me to have my freedom, and yet it took me a while to sort of figure out what that was going to be for me, how bold I was going to be able to be, how brave, how insecure, how shy as well. … I think the only thing that frees me more is the more I get to know myself, the more free I become. … I’ve gotten more confident in my voice and who I am and what it takes, what my expression is for people, what my purpose is really, and I’ve realized [my purpose is] to offer people hope and to express that by me being as much myself as I can be to people and let them know that there’s always a better place we come to, it’s just such a rollercoaster ride. And the more I’ve gotten free in that and not let myself be stifled by image or identity in what I do, the freer I become. And then it’ s just so relaxing.”

Chapter 3: On Working with Suf & Denny

I was curious to hear more about the recording process with Denison Witmer & Sufjan Stevens on last year’s release These Friends of Mine, recorded in Stevens’ New York City apartment.

“It was so fun, and we all have such different personalities and there were days where, I mean literally it was like, well good to know you guys. We’ll probably never talk again. [giggle] More for me, not because of them, because I know I’m a lot to handle personality-wise. And Denison’s silly and Sufjan’s much more kind of reserved. And he has his moments, he’s hilarious, but he’s such an individual, more than anyone I’ve ever met, I love being around people like that even more because I want to bring them out and I think maybe too much I try–it’s like, ‘Seriously, leave my apartment.’ We had such a great time and I’m really so grateful, you know, I think about that often. We were just in New York and I just remember thinking, I really feel so blessed that that even was an opportunity given to me,

And I think it’s a hilarious, great record that we didn’t intend to make, you know, so sometimes those are the greatest things, aren’t they? It’s like walking into–not that I want you to meet your husbands at a bar, but it’s–I was going to say walking into a bar, but you know those moments where life can really turn on a dime and all of a sudden it’s like, you won’t believe it, today I met the love of my life.”

When I later ask for inside scoop on Sufjan Stevens’ next state-as-album, she is coy in her email. “Don’t know what Mr. Stevens is working on currently, could be a record about outer space for all i know?”

Chapter 4: On Hearing Her Music on Television

The first time we heard the first few chords of a Rosie song on Alias, my friend Angela and squealed, so I had to ask Rosie what it felt like for her in that moment.

“You know what, I only–that’s funny, I think I’ve just seen one, cause I’m always on tour when they air. And it really happens so quickly–its amazing how publishing works, it’s such a quick move. Like I’ll get an email and they’ll say, “Rosie, do you wanna blah blah blah” and I’m like, “uh, yeah, of course I do my rent is due.”. And then it will literally air that week. But there was one, I was home on tour and all my roommates–I’m living in a house of eight girls at the time, wow. It was fun though. In the basement, cause it was all I could afford. Anyways, we all made margaritas and we watched it, and it was really weird. Thankfully the good thing about music is that it’s not you, it’s you but you’re not seeing your face, you’re not like, oh god, I’m on in five minutes and you have to see like, is that how I walk? Oh my god. Is that how big my butt is? Wow! So I can handle it a bit more. But it’s been funny. I think–I take that back, I’ve seen two. And I laughed very hard at the first, the second one I laughed really hard because it’s like, they were making sweet love. And it was playing. It was so, so gross, and I don’t remember what, it was like, oh god it was that Sally Field—”

Brothers & Sisters? I ask.

“Yes! They were making sweet, sweet love and I was like, oh no, oh, yeah, there’s my song! Oh my god! You know? It wasn’t even like porn, it’s not like it was dirty. I just thought, how funny, I never would have thought someone would be like, right now you guys are both naked, um, Rosie T. Yes, put it on. So it is really strange, but thankfully it’s not seeing my own face, my own body, my own physical being, I think I would have–I would never watch it. I couldn’t handle listening to it. But it’s moving, do you know, of course, I think wow, I never would have thought that. And thankfully, but strangely, too, it helps. But forget that, it’s just really neat to think–I never would have thought something that depressing would make it somewhere! So that’s really neat.”

Chapter 5: On Current Infatuations

What Rosie is listening to right now:

“You know the big one for me, Rogue Wave, I’m still into that record…the Iron & Wine record [The Shepherd’s Dog]…Track 3, 4, and I think 7 are amazing. I love Sam Beam and I love his music, they’re such great people too. So actually the newest one for me is, um, is Iron & Wine would be the latest record that I just got, I love it. God, I listen to so much stuff, man, everywhere, from R&B to hip hop to, like Christian radio, there are times when I’ve been, everything—it’s soul music. When I hear a soulful voice, it moves me. There’s a ton: The Shins, oh god, Patty Griffin, really, I just got one of her latest records, I don’t ever listen to myself, of course, of course not, ew ew. Midlake. Woah. It’s amazing. Their harmonies–they’re amazing. I think they might be my favorite band right now: Midlake. And I can’t remember the track you need to listen to but you’ll know cause they’ll affect you as well.”

Chapter 6: On Her Minor Obsession with Self-Help Books

“Oh, god, you know what I just read? And I can’t believe I got it, was the, and they’re making it a movie, “You Don’t…” Oh, god, now I’m gonna blank on it. I just finished it. “You Don’t Like Him as Much as You Think…” Wait–”

“He’s Just Not that Into You?,” I ask. She nods that she thinks so.

“–It is the funniest thing, it’s more about booty calls, I was like, um this is not the b–wow! People do–wow! It wasn’t what I thought. A lot of times, when I go through funks is when I love reading self-help books. I wish you guys were there at Barnes & Noble or Borders or like little, smaller bookstores in Seattle when they’re like, um, Who Am I, beep, Where Do I Go From Here, beep, I’m like, uh, it’s for my mom, she’s really down.

But lately that’s been my kick, all the psychology books and self-help books, and what I learn from them, I think they’re funny. Some things I think, this is the cheesiest–is this Dr. Phil? Cause this freaks me out. Which, I probably will buy one of his at some point.”

Chapter 7: On Falling in Love

If Rosie Thomas could tell her audience one thing, it’s “Don’t Settle.” She repeats this a few times, then goes on to talk about love versus infatuation, and how she admires couples with babies, who have to dig in their heels for the mundane routines of life, and how she craves that consistency. How she looks up to married couples stick with it for 40 years and will admit that the 40 years have been a struggle at times. Rosie shakes her head, saying, “To know that people really stood in that muck and still have chosen to love each other, oh man, that to me, that’s the biggest victory ever, that’s bravery. That’s real.”

She also opens up about falling in love with the man in her life, Jeff Shoop (who acted as tour manager and played in her trio during last fall’s gigs).

“The fellow I’m dating now–I waited a long time, you know, I was very careful, I almost got married to the last boy that I dated–and I’ll never forget, it was the weirdest moment, he said, Rosie, I just asked your dad for your hand, for your blessing, and I–you know moment in every girl’s life. And I may not be the typical girl that just, like has been thinking about my wedding my whole life. I’ve probably been the one terrified, like, oh hell no. But the first feeling I had was, I was terrified. I couldn’t figure out in my heart, was that my own fear of commitment or was that this just wasn’t the one, you know? It’s funny, you know, the relationship dissolved, which helped me to write the last record, and now the fella–you know, two days before I met Jeffrey, I prayed, you know what God, I’m done. And I’m all right with that. And I knew it, it felt so real, you know what, I’m so sorry. And I was apologizing to my own self, because you know what, I’ve never taken myself seriously enough. If a man came into my life, I never, I just though, well, we’ll date, that’s what we’ll do, and then we’ll see. And then my heart, like any girl’s heart, you get entwined, you find purpose, you think ‘this person thinks I’m amazing, so I must really be,’ and when it ends, what happens? You feel exact opposite. You think, I’m worth nothing. One person can taint your whole idea of who you are and how you feel. And it killed me that I allowed one person to do that in my life, and… you know I prayed one night, God, I’m so sorry because I had never protected my heart, I just gave it. And I said, the next time around I will not give in unless it’s the one. I just won’t. What’s the point, unless a man knows what he wants. Unless he comes to me and says Rosie, you’re so special, and I’ll tell you even more so, because I know, and I’ll say it to you in five years, ten years from now. Not just for the moment, not for a week, not ‘We’ll see how special you are in two years,” and it’s funny two days later, you know I prayed that, and what’s scary is I remember thinking, it felt so right I remember thinking, “Yeah, God, you know what, I’ll even have cats,” oh my god, I was excited. “

Jill and I, being cat ladies ourselves, nearly collapse with laughter.

“I thought, that’s it, I’ll have cats, I’ll be 40. I saw it, too, I felt like God was like, “Really? Do you really mean it?” I had to think about it. “Yeah, no I think I do.” “Really? Here’s a vision: what if you’re 40 and it never happens.” I thought about it. I’m ok. I remember thinking, why Rosie? Cause I’d rather be that then just give my heart again and be broken again, I can’t, can’t do it again. And why else? Because I’d rather be alone than the cliché of being with someone just to be with someone that maybe wouldn’t help me be a better human being, that maybe I wasn’t meant to help be a better person. I’d rather be alone and be a Godsend to someone in my own right, as an individual, than just be married in a mediocre way and suffer for that. And it killed me to say, because I really thought in my heart of hearts, it’ll really be a long time, won’t it? And I remember thinking, but that’s alright, it’s ok, I’ll live in a basement, I’ll bring joy to be people, I’ll go visit my friends who have babies, I’ll be alright.

And about three days latter, Jeffrey, who was my friend for a long time, came to me and said, “Rosie, I don’t mean to bother you, we’ve been friends for a long time,” he said, “but I choose you.” I said, sorry? He said, “I choose you. And you know what I mean by that?” This is crazy, this is even what’s crazier: He said, “Do you know what I mean by that?” I said, “Well, I think so, but I’ve heard that before.” It wasn’t even like I was like, prove yourself to me.

But what’s so amazing is he said, “You know what’s wrong with men, Rosie, is that most men make the choice for a moment but they don’t consider what they really mean by it. They’re not thinking, well you better know, as a man, what you mean by that, you’ll hurt a girl. Most men make it freely and no wonder women get hurt.“ But it was so neat because it was the exact thing I prayed for, he said, “But I’m telling you, do you understand my words, I’m saying that from this point forward, that no matter what we go through, no matter what it is, I mean it: I choose you. I know that this is what the Lord wants, and I’m so sorry for men who have been uncareful with that, who have thought yeah, for now I will.” And I see it all the time, I see friends do it, I see “You will not believe it, I met Kelly and she is the one,” and then six months later, sure enough, “What happened to Kelly?” “Uh, yeah, I don’t know, it kinda got too real,” or, “She wasn’t as cute as I thought,” she wasn’t as funny, and it was the first time I heard it and I remember thinking, oh my god, that’s it.

And as scary as it is, I realized it’s because I let it go, I realize for the first time I saw my worth, I swear to you it’s because I did, because my worth–I would rather be alone, because that’s how much I saw my worth and I told girls, I would walk around at that time, and got on this kick, because I really believe if we tell ourselves things we’ll start to believe it. So I would introduce myself to people, “Hi, I’m Rosie,” “Nice to meet you, Rosie,” “and I’m a lovely woman,” I’d tell ‘em. All the time. “Hi, I’m Rosie, I’m a lovely woman,” people on the street. I would get pizza: “Hi, how much is it?” Blah blah blah. “Oh, great, oh I’m Rosie,” “Oh, I’m Bob.” “I’m a lovely woman.” “Oh, ok.” And I just though, if I tell myself that enough, then I believe it. And maybe if I believed it, then if someone did come along or didn’t, then I could still hold my head up high and think, I’m a lovely woman, you know? And that’s what I encourage women, because I think so many of us do settle, but also, so many of us do have such wrong expectations as well, you know what I mean?”

In a subsequent follow-up email, Rosie shares the rest of the story: she’s getting married to ‘Jeffy,’ as she referred to him in the interview. Sure enough, this August they will wed on her grandfather’s farm.

The Epilogue: On Kissing Steve Zahn & What’s Next

You heard it here first: Rosie Thomas will soon make her big screen debut, playing Steve Zahn’s character’s ex-girlfriend in the upcoming Calvin Marshall. In the same email she shared her wedding news, she also wrote:

“My name was Sondra and we had a kissing scene!! How crazy is that? I struggle with PDA in public with my own fella and I had a kissing scene with Mr. Zahn! Every time they yelled cut, I screamed “I’m an actress!!” one of the most exciting weeks of my life honestly, I was glowing…loooved every minute of being there.

Currently working on a Christmas album and about to go to Texas to do some pre production with Sam Beam for the next record, got a bowl cut last week and getting Touring the last week of March with Teddy Thompson and going to Europe in April to do a tour over there.

…geez I guess a lot has gone on since we last spoke!! Wowsers! Doggonnit Jim! Thats alot!”

As far as the conversation with Rosie that night at the Birchmere, there was so much more (12 single-spaced pages of 12 pt. font in the final transcription—and that’s before the tape was shut off and the tears started flowing!).

It was, speaking frankly, a dream come true for a fan who once had her heart broken, and who once played a song over and over and over to heal. So please allow me this much: More Rosie & Sam Beam! Rosie’s gonna be in a movie with Steve Zahn! Rosie’s gettin’ hitched! Angela, I can hear you squealing right along.

I’m about ready to crap my pants myself.

Happy Valentine’s Day from the team at The Drop.

The majority of the comments by Rosie Thomas were recorded October 27, 2007 at the Birchmere in Alexandria, Virginia, with Rosie Thomas, myself, and my best friend Jill, who cried right along with us. We did, after all, first become friends because I approached her on the set of an independent film and within five minutes, discovered we both loved Rosie Thomas & Over the Rhine—the rest has become a beautiful, hilarious story unfolding.

Special thanks to Dan Portnoy.