Chelsea is not a metaphor.

CITS #92 | May 22, 2025

You never know when someone you just met is about to become one of the most important people in your life.

I certainly didn’t—when I crash-landed into my half-furnished childhood bedroom at twenty-five, my dreams of a globe-spanning entrepreneurial empire in pieces. I was burned out, with a college degree and the debt that came with it but no plans, no job prospects, and no friends who lived in the same city as me. The only thing I had going for me was that I had managed to get and stay sober for a few years. After a few months of being morose and gaining weight, someone pointed me in the direction of a few places where sober young people around my age often hung out.

Reverse culture shock hit hard. After spending time with Chinese nationals and expats, I didn't know how to fit in with American young people my age at all. The first time I tried to hang out, I wore an oversized white hoodie (that people still make fun of for some reason) and heard a few people mention the rapper Riff Raff. I went home and watched every Riff Raff YouTube video I could find, then tried to impress people with Riff Raff facts for weeks. Despite this, some kind people eventually started inviting me out.

The first people who were nice to me weren't my friends per se. There was a large cast of characters amongst this group of sober people, and one of the ones on the periphery was Chelsea. At first she seemed unlike any of the people I knew growing up. I went to Catholic school for thirteen years, the last four of which were with all boys, before going to a fairly conservative state school, then moving to China where I hoped to be an international entrepreneur. Chelsea had a platinum blonde asymmetrical pixie cut with side-swept bangs and was never dressed casually, always wearing revealing, form-fitting athletic clothes, club dresses, or designer jeans and moto jackets. She was a college student who worked as a personal trainer, straight out of central casting for a role like "cool hot twenty-something in a big city."

I had known women who were cool, stylish, and attractive, but I was only recently not a giant dork myself. I thought Chelsea was nice, but she was only one more person in the friend group. I had never spent time casually hanging out with women like that and not been in an environment where I was pursuing them. I did not know what we might have in common. Had we not had a chance encounter with a mutual friend, my life would be completely different. One night after a big hangout with a dozen or so of us, both of us decided to hang behind with our friend, Ryan. This was the first time I got to know her really well. Ryan wasn't much of a talker so Chelsea and I ended up filling the dead air. What surprised me the most was that Chelsea was, frankly, strange. We had similar senses of humor and both enjoyed reading books (not common in this crowd). She and I exchanged phone numbers and started to text about random things.

If this were a different kind of story, I might write about how we started to get closer, fall in love, yadda yadda, but it's not that kind of story. I count Chelsea as one of my best friends. Before we got to be good friends, I don't think I would have outright argued, "men and women can't be great friends," but I think deep down I suspected that they couldn’t. And that's because I think I used to believe that platonic relationships between straight men and women were just stunted romantic relationships, or romantic relationships waiting to happen. That's only because I didn't know what such a friendship could offer, or how much it could add to your life. And now I do, because of Chelsea.

When we were first friends, I sometimes thought she was putting on airs. Between sharing memes, I would ask her about hot-button issues, inquiring which side she took. A very "Chelsea" answer would be to subvert the question, saying there was something wrong with the frame, and she took issue with something at a much deeper level even than that. Like, I once asked her if I was responding fairly to an email or Facebook comment I received that I thought was a bit much and she told me that she was the wrong person to ask, because she was capable of great evil. (Don't worry--I still tease her about this.) Another classic “Chelsea” move would be to bring up a highly unlikely, only tangentially related anecdote that is nonetheless certainly true and puts a dead stop to the conversation. Like, I once asked her if she thought TikTok was more corrosive than Instagram. And she said she doesn't support or use TikTok, because she downloaded it once and it immediately showed her a snuff film. Is it true? I don't know. But the conversation was over.

I had other friends early on in my friendship with Chelsea who encouraged me to ask Chelsea out, but I didn't. Not because I didn't think she was attractive, or she didn't add to my life, but because she added to my life–and I to hers–in a way that was different and better than had I attempted to make us into something different. I didn’t think that she was just a substitute girlfriend, but a good friend. (Some people might find it funny, or even sad, that I didn’t realize this until my mid-twenties. Others might debate whether it’s even possible. But I share it for the benefit of anyone who’s somewhere in the middle—who, like I was, might still be learning what friendship can mean.) The better I got to know her, the more I realized how individuated she was. There are few people I know who know themselves as well as she does, and anyone who knows her well can attest to this. People have asked me about Chelsea before, thinking she's projecting some opinion or version of herself, or asking what makes her actually tick, but I tell them, "no, there’s not like a deeper mystery, what you see is what you get. Chelsea is Chelsea all the time."

And I don't know whether it is the cause or effect of this, but she sees people for who they are--not who they're projecting, but who they really are. When I started writing, she was one of the first people who subscribed and one of the first people who really got what I was trying to do. She gave great feedback for what was on the page, but also understood the project in context of what I eventually wanted to build. I'd share some insane creative ambition and she'd support it not with flattery but with clarity, "yeah, you can probably do that, you have the talent, you just need to put in the work." Contrast this with her time as my erstwhile personal trainer. I would share some similarly ambitious physical goal and she would just straight-up tell me, "dude, I love the enthusiasm, but there's no way. I've seen you switch plans too many times. You probably just can't do that. " It's a rare combination of seeing people for who they authentically are and refining that vision with her experience of them.

This is why I implicitly trust her judgement of people's character. And why I would go to her with my problems with women. When I was about 26, I was "on the apps" like everyone else. I realized I was screwing up any chance at a healthy long-term relationship, so I tried to straighten out and be sincere. I told Chelsea about this multiple times, one day saying, "it's funny, when I’m being self-destructive or wasting time, dating apps are a superpower, but when I try to be open to meeting someone good for me, nothing happens." And she told me that it was weird that her best friend Raquell was having the same problem. After I shared my indignation that she hadn't told me Raquell was single–apparently for over six months after splitting from her long-term boyfriend–Chelsea told me she assumed we both knew the other one was single. Chelsea gave me her excited blessing to pursue Raquell, dropped some clues about what Raquell might like, and told me why we'd be good together.

And that is how I met my wife.

Chelsea is still Raquell's best friend, but I count Chelsea among my best friends too. Many times since we've been together, Chelsea and Raquell have taken a "girls' trip" somewhere. They have a deep relationship that predates me, and I’m glad it does. I have a deep relationship with Chelsea that predates my relationship with Raquell, and she’s glad it does. At the speed I generate ideas and drafts for my blog, my wife gets tired of me talking about it. And Chelsea is probably my most active beta reader and editor. This would be a big favor from anybody, but I've written before about how the people closest to you are often not at all interested in what you write about once you get started, so it is especially touching. My three-year-old daughter knows Chelsea by name and will ask for her, or name the things that Chelsea has given to her in her room. Chelsea is a crucial part of my "village" and an intimate part of the inner life of everyone in my family.

As a writer, I'm always tempted to reduce (or transform) things to metaphors--even people. But with Chelsea, that's tough. She jokes to people that she's my wife's second husband and my second wife.

If this were a novel and I were the protagonist, maybe Chelsea would be my foil—the character whose traits contrast with mine to bring them into sharper focus. I’m always musing about what to do next, tentative, a little jolly; Chelsea is independent, intrepid, and just a little sharp around the edges.

But the trouble with that is: people aren’t metaphors.

To try to capture her along one dimension would be to cheapen what she’s brought into my life.

I just hope that in trying to write about her, she feels as seen as she makes others feel.

---

I wrote this as a belated birthday gift for Chelsea. Not long after I started drafting it, she was diagnosed with leukemia. The prognosis is good, but the process will take about a year, during which she won’t be able to work.

She’s facing it the way she faces everything—on her own terms, with humor and honesty.

If you’d like to chip in for her birthday, here’s her GoFundMe—

---

Updates and Links

Hello friends. You may be wondering what CITS #92 is—or you may have noticed that I started Friday Footnotes, experimented a bit, published every week for four weeks, and then dipped out for a month.

Offline, I've had one of the biggest months of my professional life. A huge transition is coming that will change how I write, publish, and talk about my life here. It's upended a lot of my rebrand plans.

I'll have more to say before mid-summer. For now, I'm reverting to my original format: weekly posts on Thursday mornings, numbered for reference, with extras when I feel like it. Check my updated About page here for a longer (but still brief) explanation.