Catching Up With Caitlin (After 31 Years)

My Fellow Shennyer:

How often do you think about old classmates you haven’t seen in decades? For me, I feel like it’s a lot—especially while working through this chapter on the closet. Inevitably, I turn to the cast of characters who populated those years: the classmates whose names I still remember, the friends I lost touch with. I daydream often of getting a drink with one of them, hearing about their lives, trying to see what vestiges of the child still thrum behind the eyes of this adult.

I think it’s out of a desire for narrative—or maybe, more darkly, social engineering experiments. The kids I went to the same school with, grew up in the same suburban town with: what variables in the years since have acted on them? What has the wild mess of infinite options changed us all into?

That said, I’ve never flown home for any of my high school reunions (they’re always in the middle of the summer, when I want to travel anywhere other than Herndon, Va.). So this week’s Shenny is a bit of a dream come true, given the Main Matter below. And I’m happy to be continuing my 3Q’s w/ series of issues, with let’s hope more to come.

Hope you enjoy, and if you’re a person with a school year that’s started, all my best for a great one.

Yours:
Dave

Endorsements

1. Egalitarian Toilet Seat Rules
Short version: everyone has to lift something, everyone has to lower something down. My mother- and sister-in-law visited us last week, and it was both a lovely time and a whole lot of walking into bathrooms with the toilet lid up. Were the roles reversed, I imagine they’d complain about all the toilet seats left up—except that I practice egalitarian toilet seat rules. In this boring, old war of the heterosexual sexes, it seems that most people believe men, in a kind of noblesse oblige, should lower the seat after they’re done pissing. But toilet seats have lids, not just seats, and when you leave a toilet seat-down / lid-up, what’s to stop a bathroom shelf article from falling into the water? Everyone reading this who uses toilets: close the lid when you’re done. Nobody gets a free pee.

2. U.S./World Tabs on Newsletter Apps
I read the Chronicle and the LA Times on my phone, sometimes the Washington Post, and always in the main feed are click-enticing stories I don’t want to read. The Times is lousy at leaving such stories in the main feed for a week or more. I get that newspapers need to make money, and algorithmically optimizing engagement is one way to do that, but paying for my news, I scroll immediately over to the ‘US & World’ tab, as the Chronicle calls it. (The Times calls it ‘World & Nation’, hidden under the ‘More’ tab; the Post’s best offer is ‘Latest Headlines’.) Here are some stories I've found recently that never popped up in my main feed:

• Nasa restores contact with Voyager 2 spacecraft after mistake led to weeks of silence (I didn't even know contact had been lost)

• Ecuadoreans reject oil drilling in protected area of the Amazon, forcing state to end operations

• California AG opens investigation into California district forcing educators to out trans students

• Court rejects S.F. DA Brooke Jenkins' [sic] decision to drop resentencing case initiated by Boudin (I noted who got their first name mentioned and who did not)

Are we all given the same news app homepage? Is it like a front page that editors pick stories for, or is everything an algorithm now? Either way, these are the kinds of stories I want to give engagement metrics to, to keep them alive and paid for.

3Q’s with Caitlin Upshaw,
A Friend I Haven’t Talked To in 31 Years

In 1992, I tried out with some friends for the 8th-grade musical: Rock ‘N’ Roll, a sockhopping Grease ripoff. I landed the line-less role of background maltshopper. Who owned that malt shop? Nobody remembers the name, so let’s say it was Rosie, and Rosie was played by Caitlin Upshaw. Caitlin was in theater classes with my friends BJ and Chris, more of a friend-of-a-friend, but in the long hours of sitting around the auditorium waiting for our scenes to be rehearsed, we—in a bit of a Goth dalliance—would entertain ourselves with jokes about doom and the macabre.

Rock ‘N’ Roll had a 3-night run in May, then Caitlin moved across the country and I never saw her again. Of all the people I went to middle school with, what was is it about Caitlin that made me reconnect with her online? She had a certain quality I remembered; she seemed more self-assured than the rest of us. Or it was like she was psychically attuned to a more grown-up way of life. She reminded me of my eldest sister.

When I tapped to follow Caitlin on Instagram, I saw that in the last three decades she’d found herself a wife. I felt suddenly giddy. It happens every time I learn that someone from back then is now queer: we weren’t alone. I mean: we were and we weren’t—the infrastructure needed to help queer kids recognize each other (or even themselves) wasn’t there yet in Herndon, Va. in 1992.

I wanted to reach out to Caitlin to get a sense of her experience growing up queer in my hometown, but also just to reconnect in a more substantial way than just following one another on socials. I wish we could’ve done it in person, but Caitlin lives in Portland, Ore., so 3Q’s would have to cut it.

Q: Fill me in on what you’ve been up to since 1992.

Lord, that was a long time ago! My family moved to Eugene in 1992—a major culture shock after growing up in Northern Virginia—and it ended up being such a wonderful thing for the whole family. My dad had been a reporter in D.C. and changed careers to teach at the University of Oregon. Eugene is a college town, a hippie town, and a great place to go to high school. I found my place as the theater/choir kid and had a great time in high school doing theater nearly constantly—there was a theater downtown where I found a kind of home and ended up getting a ton of stage experience during those years.

After high school, I went to NYU/Tisch School of the Arts for acting, but I ended up changing my major after being in NY for two years. Thanks to the Clinton/Lewinsky scandal (oof, I’m old), I felt compelled to switch to journalism and transferred to the University of Oregon, where my dad taught TV news. I moved back to NY after college graduation, just before 9/11, which then sent me packing for Portland—still a semi-big city but closer to home and further from that event.

I’ve been in Portland since October 2001. I love it here and can’t imagine living anywhere else. I’ve discovered mountaineering, trail running, a passion for racial justice, an arts community, and a group of friends who genuinely feel like family. Over the last 20 years I’ve gone to law school, built a career in law and Human Resources, and more recently ditched that career to focus back on music and theater. I’m now teaching voice lessons and running vocal performance workshops, along with performing, and I feel very fortunate that I get to do what I love full-time.

Q: Back when you knew me I was in a confusing kind of denial: I was fantasizing about my P.E. teacher and my bully, but never even considered I could be gay. What was your experience of queerness like? What about your thoughts or experiences of queer people in general?

I also had no idea of my queerness in middle school. Of course, once I came out, I remembered how I used to be obsessed with some of the women on TV shows I watched as a kid/tween. In high school theatre circles, everyone was kind of fluid in one way or another, so I never saw any of my thoughts or behaviors as anything other than ‘normal’ for my peer group. I just never clocked it as queerness until I was much older.

It wasn’t until I was in my early 20s and met a woman at work who was out and a bit butch, and all of a sudden FASCINATING to me, that I realized I was gay. I blame my obliviousness on being a generally happy kid—I definitely passed as straight and didn’t experience much social trauma, so I never had to question anything. I also genuinely enjoyed dating the boys I dated as a teenager, so it was more like I just didn’t know what I was missing, until I knew.

I met my wife when I was 27, had two kids, and the rest is history. Now we’re so square and conventional that I often forget that we aren’t your typical family. We have the privilege of living in a very queer-friendly city, so it’s never an issue we really have to think about.

Q: What memories do you have of Rock 'N' Roll—good or bad? How did that show prepare you for a career in musical theatre?

Oh, Rock ‘N’ Roll. I don’t remember much detail about middle school, but I definitely remember that show. One of the things that stuck with me was getting cast as an adult, which tends to happen to bigger, more mature-looking kids. To a 13-year-old girl, that felt awful. I ended up having fun and loving the role, but at the time I thought the casting choice meant I was too tall/fat/ugly to play one of the teenagers. Someone in the audience told me later that everyone thought I hadn’t really been singing my role—that the show played a recording and I just lip synced along. I remember being both angry and flattered!

It wasn’t the first time I felt overly aware of my body. I was a classic girl child of the 80s, which meant my mom was always on a diet and I was always reading magazines that told me that my main goals in life should be thinness and conventional beauty. I was put on diets as early as age 8 or 9, and I was ‘incentivized’ to lose weight with promises of new clothes, money, etc. At the time it seemed normal to me, but as an adult woman who (finally) celebrates the worthiness of every type of body, I can see it as deeply toxic. I choose not to be angry with my parents, who were themselves immersed in a culture that told them this was appropriate parenting. Looking back at elementary and middle school, I was not really a fat kid—just a person who was a bit curvy and tall for her age—but I definitely felt like a classic fat kid. There were times I liked being tall, but overall I existed with a constant desire to be a much smaller, delicate person. It wasn’t until around age 40 that I finally stopped trying to shrink my body through restrictive diets.

Overall, I do think RNR prepared me for the theater I did as I got older—it was probably the biggest production I had done to that point, and I had some real confidence-boosting moments during that process (even though I felt huge and ugly in my role). I’m also thankful in general that I did theater so much as a kid, because it informs the way I build workshops for budding theater kids. I know the benefits and the pains, so I can prepare for my students to experience all of that.

Ultimately, the arts will save us all because they teach empathy and force us to see each other as human beings worth celebrating. Fund the arts, y’all!

Caitlin works in Portland as an actor and voice coach for young artists and adults. Learn more at caitlinupshaw.com.

This week’s thing I did not buy at the antique store is this painting of a guilt-ridden girl stealing a bird’s nest.