Tomorrow morning, while I sleep, my friend Rich is going to kiss his wife goodbye. I imagine he will linger a little longer than usual at the bedside of his (hopefully) sleeping toddler son and the crib of his six month old daughter. Then he will catch a flight to North Carolina where he will spend an uncertain amount of time preparing for a deployment of an uncertain amount of time. My friend Rich is going to Afghanistan.

On Saturday night, Rich and his wife, Diana, had a few friends to their house to say good-bye…

…and while Rich isn’t a hippie, I have to admit I was a little stunned by the new, shorter haircut. I couldn’t help but run my fingers over it when he stepped into the hall to greet me. When I say he’s not a hippie, I mean that only in the physical sense because, really, he’s a hippie with a crew cut. The man ran naked on election night and what could possibly be more hippie than running naked through the streets on election night?

You see, Rich is a tree-hugger extraordinaire. I used to bump into him at the farmer’s market on occasion (before he was hypnotized into thinking the ‘burbs were better than the ‘urbs) and he was always weighted down with organic fruits and veggies. Diana finally put him on a budget because, untethered, he would blow their monthly grocery allowance in one evening. The man has no self control when it comes to being green: He drives a Prius, and he loveslovesLOVES Al Gore. I think he might just have sex with Al Gore if doing so wouldn’t get him kicked out of the Navy. Then again…

Rich is a uniquely special kind of person with an unusual blend of wit and naiveté. He has an unassuming innocence that I always find refreshing and sweet. His hugs are strong and generous and sincere. His eyes shimmer when he smiles and he throws his head back when he laughs, face open to the sky. Rich is wholesome and endlessly positive. All of his sentences end with his voice in an upward lilt. He is the nicest—absolute nicest—guy I have ever met. I’m pretty sure I’m not the only person who feels this way about him. And yet.

He has a mischievous streak that makes him irresistibly endearing. Last summer, he blew my mind when he launched into a spontaneous version of The Aristocrats. I’d never heard Rich say the word “fuck,” much less “pussy.” Certainly, I’d never heard him say those kinds of words as they pertain to a grandmother and a donkey, but use them he did. And those are the G-rated words he used in his storytelling! Rich was a poet that night, a weaver of tales, a builder of imagery. He was very, very naughty and, well…I do like my friends a little naughty.

He and our friend Steve riffed off one another seamlessly, making the story progressively more absurd and obscene until the group of us listening was practically drooling over ourselves with laughter. Without question, it was the raunchiest joke I’ve ever heard in my life.

Despite intentions, Rich didn’t get around to the joke the other night. The evening was filled with laughter but there were also some tears. Mine came in private moments while reading emails he’d sent home during a deployment to Iraq in 2004.

Diana had placed all of her memorabilia–the scrapbooks, the emails, the pocket guides–out on their coffee table for us to browse. “It’s a different world,” he wrote. “Nothing I really trained for.”

It was all personal, much of it was dark and I feel honored to be included in their lives in such an intimate way. But it was heart-wrenching, to be honest, to have a glimpse into this other side of Rich. It made me worry for him.

This is a new experience for me: I’ve never known anyone in the military. I’ve never gone to a send off. I’ve never had to say such a serious goodbye. Even while they worked to put me and our other friends at ease, I felt awkward at moments and wasn’t really sure what to say to Rich or to Diana. My hope, of course, is the same as I suppose everyone else’s hope is when they send someone they love off to war: That they stay safe, that what they see doesn’t scar them too deeply and that they come home to those of us who love them as quickly as possible.