This week's Interrogation was supposed to be an interview with Stephin Merritt. It didn't go so well. The last time you tried to interview him, at Bumbershoot in 2000, didn't go so well either, right?

The Magnetic Fields came to play Bumbershoot, and the organizers asked if I'd be up for moderating a "songwriters salon" featuring Stephin Merritt and Sally Timms of the Mekons. I love both bands, so I said yes. A couple of days before the event, Timms had a family emergency and had to bail, so instead of moderating a discussion between Timms and Merritt, I ended up doing a one-on-one, live-onstage interview with Merritt, and it was a fucking disaster.

What happened?

Very little. At the time of the Bumbershoot interview, I was completely infatuated with 69 Love Songs—when I wasn't listening to it, I was thinking about it, and when I wasn't doing either, I was swimming through the related media coverage: the Village Voice cover story, the Terry Gross Fresh Air interview, Merritt's past writings for Time Out New York, everything I could find. I was a freak, and my rabid fandom made me the worst interviewer in the world.

How so?

I knew from all my reading that he was a notoriously difficult and prickly interviewee, even a notoriously difficult and prickly person—in the Village Voice profile, Merritt's former coworkers at Spin told how they were sure the mute and scowly copy editor hated their guts. So, I thought I'd honor this great and prickly artist by bringing only the freshest and most fascinating questions to the interview—I wouldn't bore him with any of the same old questions about love songs he'd been answering for months. Unfortunately, these were exactly the questions the audience was hungry to hear Merritt answer, and my three-part questions about the intricate conceptual differences between Merritt's various band configurations and the forthcoming 6ths album—which none of the audience had heard yet, not having advance press copies—bored and confused everyone.

So it was your fault.

Well, Merritt's one-word answers and long stretches of scowly muteness didn't help. Eventually, we just sat there, silently staring at each other. It was a standoff—he wasn't going to force himself to be bubbly and forthcoming for my sake, and I wasn't going to force myself into some solicitous Larry King buffoonery for his sake. It was extremely odd and awkward, perhaps one of the great Dada moments in media relations. Afterward, Merritt came up to me and apologized.

That's nice. Then, a week ago, you tried to interview him again for this column. How'd you fuck it up this time?

I figured a lot of the difficulty of our first encounter came from the live setting— interviews-as-performance are weird things, and I hoped restricting our conversation to a private phone call would help things. I was wrong.

What happened?

It started fine—I'd prepped a bunch of straightforward, nonwonky questions about Distortion and the tour and his surprise side career as the voice of Volvo, and braced myself for the long pauses. Before his publicist connected us, she asked, "Have you ever interviewed Stephin before?" I told her, "Yes, but tell me what you tell people who haven't." She said that he spoke very slowly and thoughtfully and essentially that I shouldn't let it spook me. I thanked her for the warning and she put me through. But as soon as I heard his first long, exasperated sigh, I was doomed.

What do you mean?

It's like I had post-traumatic stress disorder. Just hearing his voice dragged me back to the horror of the Bumbershoot fiasco, where we'd been trapped onstage. Only this time, it was just the two of us on the phone, and I could feasibly end our suffering at any time without leaving an audience high and dry. So I slogged through a few short questions, and then I hung up.

What did you manage to ask him before pussing out?

I asked about the recording of Distortion, and the design of the CD cover, and when he deigned to speak, he was actually pretty forthcoming. He explained how they rigged the mics and amps to get feedback out of the piano, and how the Distortion artwork was his idea, originally intended for another record that's since been shelved, then resurrected as a twist on the distortion theme.

That sounds perfectly lovely.

Yeah, but what these recollections can't capture is the deep, inherent contempt for the whole interview endeavor that seems to radiate from the core of Merritt's being. Maybe it's deep thoughtfulness or light Asperger's, but it affects me like the smell of burning hair. And here's where my deep love and admiration for Merritt's work bites me in the ass as an interviewer: The way I see it, the world is packed with people with decent social skills and zero songwriting ability, and those rare folks with world-historically brilliant songwriting abilities and compromised social skills are worth coddling. Maybe if I weren't so admiring and protective of Stephin Merritt's artistry I'd be able to interrogate the shit out of him, go for the jugular with questions sure to piss him off and clam him up, like, "Why do you still agree to do interviews when it's clear you'd rather eat glass?" or ridiculously offensive stuff like, "Why do you hate black people so much?" Maybe if I weren't such a fan, I could at least force him to be the one who hangs up.

The Magnetic Fields play Town Hall Thurs–Fri March 6–7, 8 pm, $27.50, all ages. Sold out.