Wednesday, December 31, 2025

The Different Kinds of Cool: A Second Perspective

Many years ago, when I used to write this blog on a regular basis, I wrote one about the different ways that celebrities can be cool. And I'm absolutely going to use this moment to mention that one of the people I went on about at great length, Felicia Day, has since become very good friends with someone I am also friends with, which makes me feel happy every time I think of it.

I mean... I think we were friends.

I mean... I know we were friends. But you know how time does that thing?

I remember once he and I were standing on a corner in Tribecca talking about nothing in particular, and he shared this exceptionally emotional thought with me that I still think about to this day. But I'm not going to tell you what it was.

I do often wonder if he remembers that day. Or me at all, beyond the very general outline. But I hope he does. He's cool as Hell, and I know for a fact that he remembers my name because every decade or so we run into each other and exchange the standard pleasantries that you do with that sort of person at those sorts of times. He's also super successful and I'm really happy about that, even though we don't really know each other much anymore.

Truth be told, I'm actually sort of friends with a surprising number of people you've probably heard of. Just one of those weird things that life does.

When I was 13 years old, back in 1985, I met my first best friend. We still talk, although not terribly often, which is mostly my fault. We grew up in the Minneapolis area, but when we were both 15 his family moved out to Massachusetts, which hindered sleepovers. But for many years we did a better job at staying in touch than we currently do (again, entirely my fault for reasons that we're about to explore.)

The summer after my Freshman year of college and his senior year of high school (quirk of when our birthday's land and the American school system: He's actually about a month older than me), my mother bought me a plane ticket to go and see him for a week on the East Coast. And while I was there, I met his group of four close friends. (I think it was four. The memory does tend to go.)

It was an amazing trip. Because it was Massachusetts, I feel obligated to say that it was wicked awesome.

The thing is, my friend in question has since gone on to establish one of the longest running improv monoliths in the country, one of his other friends from that group has since become an award winning filmmaker and moved himself and his family to France, and one of the others has settled down happily in Hawai'i where he's had several books published.

The point I'm circling around is something that I only just realized this evening. (For the record, I'm writing this at around 1 AM, January 1st, 2026)

My friend (and I'll always be proud to call him that) is what we might term as 'Group Cool'. People like him. He's insanely talented. He tends to accumulate cool and successful people around himself while also succeeding on his own. He also became good friends with the Tribecca friend I mentioned earlier through circumstances completely unrelated to me, which is a funny an interesting story for another time.

And if I'm being honest with myself and you, sometimes I've been sad about that. 

But it occurs to me that, much like my earlier post here about how Felicia Day is a different kind of cool that Joseph Gorden Levitt, the same is true here.

I once mentioned in these posts, (in a column largely concerned with processing my feelings about someone I loved very much choosing to end their own life), that I liked the inside of my own head. But I never really addressed it further. But then a number of things made me stop and think about it.

To make a long story short, in the last couple of years I've reconnected with at least four people from my past who went out of their way to tell me how much I meant to them and how disappointed they were that we never hung out more and became better friends.

Which was a bit of a surprise to me, since in all cases I thought that they only tolerated me as part of other company and had no idea that we could have had so much more friendship.

There's nothing I can do now to go back and fix that, but what I can do now is square that circle and do my best to work on myself, and this is where I've ended up.

I'm solitary cool.

I was so busy staying inside my own head that I never noticed that people genuinely liked me. And believe me, I'm doing my best to make amends for that. But at the same time, I'm trying to give myself the grace to know that it's ok for both knowing that people love you, and that it's ok to need time alone in your head. I wish that I had shown more gratitude to the people that didn't realize that I didn't understand that at the time.

So, I'm going to call some out. This is not a complete list.

Michael Franssen - I thought you were so much cooler than I was that I genuinely never knew that you thought we were friends. I thought I was a mile beneath you. Still do.

Bill Sloan - You're not only one of the funniest men on the planet, not only the model for what a parent should be, you're also honestly the kindest soul I've ever known. And I've known a few good ones. Looking back, you made a Herculean effort to be my friend, and I was so sure that you were cooler than me that I didn't notice. Which will be my loss eternally.

Sean McKenna - You could not have invited me to more of your closest family events and drinks, and yet I had such a fixed idea in my head that you were better than me that I never clocked that that was happening. Years later you told me that I was one of the people that you most looked forward to hanging out with when you moved to the city and that it just never happened. That was my fault, and I missed a great friend through my own stupidity.

Jill and Brian - You both know the many things I need to apologize for. Know that I do and miss you both.

And Hell, there's so many more. I'll just add that Audrey Crabtree is one of the most talented people on the planet and I should have... I don't know. Been better.

So, anyway, I still like the inside of my head. I like that it does weird shit and that I very often don't really track what other people are telling me. (That part does make holding down a job sometimes difficult though.)

I'm really trying to include inside there that 'There are people that really think a lot of you, and you need to do better by them. Just for example, you never even mentioned Victor Varnado in this entire article, and you love him like a brother,'

So. Here comes 2026. And I'm really trying to work on being OK with both solitary and letting people think I'm cool, We'll see how that goes,


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