Thank you Cary. The LW is trying too, too desperately to stay cool! To be quirky and different! To the point that her letter makes it sound like she doesn't really exist at all. And I agree, if I read you answer correctly, that a big part of growing up is figuring out that you can just be & do. Not just that, but that it doesn't matter what that being & doing looks like to the outside world - and that when you are living with an overshadowing awareness of trying to look cool & quirky for whoever's watching, whoever's watching can see it for exactly what it is and finds it pathetic and annoying, not cool & different.

I grew up in that postmodern soup of gesture too, and all the time I see my middle/high school self in the kids who are basically performing, talking loudly to each other for the benefit of onlookers and not b/c of anything real. I feel infinitely lucky that I got to leave that behind earlier than the LW, probably by virtue of the friends and work environment I found in my early 20s. Because once you find yourself somewhere where those gestures don't matter, and people don't look impressed when you do your "look how quirky and well-informed I am" routine, ultimately it's a total relief. And you don't implode, and you don't start liking really boring things. You just are suddenly, wonderfully free to do what you enjoy, "consume" (ugh) what you enjoy, let go of the desire to think of yourself as "engaging, eclectic and informed," and feel no deep psychic wounds when someone knows something you don't. The adult world is very tolerant of the fact that not everyone knows everything and that everyone brings different experiences & passions to the table. But only once you become comfortable with your own self in that regard - until you do, you're trapped in a stressful hipster pissing contest that isn't really all that much fun.

I wonder if this guy, wonderful but romantically boring to her, is a little too relaxed on this front, and it scares the LW? Maybe he has grown up in the way she hasn't, and he's into a lot of the things she's into but he isn't hyper about it, and since she still is and so many of her friends still are, she's on some level judging & embarassed by him, even though on other levels he passes the sniff test (a slightly snobby classist sniff test, although I don't blame her for not wanting to be with someone who isn't into the same things she is). If so, maybe she should let go a little bit. Spend time with him, relax with him, enjoy things without needing to "consume" them conspicuously for the sake of identity-building and hipsterness-proving. And not worry about whether people see them together and are impressed by how cool they both look. Because I think that's the wonderful part of growing up - just learning to be comfortable - and a lot of times it takes being around people who are there already to get there yourself. We're social beings, after all, and there's definitely something about being with people who like us when we don't try hard that makes us feel safe. I guess that's what makes single people think everyone becomes boring when they become part of a couple! But even if it doesn't ultimately work out romantically with this guy, maybe he'll help her find the space to be a little boring from time to time - just enough that she can start to enjoy just being. I really don't think anyone will think she's less cool if she does - except, maybe, for people who judge out of the very insecurity that is causing her to judge this guy and prompting her to write this letter. In which case, I guess it becomes her turn to put someone at ease by making it OK to tone down the gesture...

This was once uttered to me by a colleague. I'm sure she said it because, looking down at my feet, she saw that I was a a Miu-Miu stiletto-wearing fashionista and expected me to agree. I am proud to say that I did not - she was looking at the wrong shoes to guess my feelings about men and symbols of cool. She should have been looking at my then-husband's shoes - Florsheims! Three years old and looking like old baked potatoes. He chose shoes for comfort, put them on and forgot about them until they developed holes in the soles. Then he went out and bought another pair of baked-potatoes-in-the-making. He wore Gap khakis, too. The kind with pleats. With dark socks.

To this day I think he is one of the coolest people I've ever known - and anyone who knows him thinks this too. He's brilliant, funny, a strange sense of humor, a vast and killer music collection. He is smarter than almost everyone around him but few people realize this - he feels no need to show his knowledge off. If he can't find something nice to say about someone (rare) he chooses not to say anything - he listens instead. He was (is) one of the few truly confident people I have ever known - a confidence that came from deep within, unaided by yoga or being a vegan or any other pseduo-enlightenment claptrap. He fits many stereotypes - e.g. a midwestern guy who eats meat and likes beer and televised sports - but he is none of them. He just has this sense of self, this core being, that most people just don't seem to have. I learned a lot being married to him. I (hopefully) stoppped being such a pain in the ass about symbols of coolness, uniqueness, acceptability. With him as a role model of just being, I became my authentic self. Looked down one day and realized my shoes, though for many undoubtedly more 'cool' than my husband's Florsheims, were ultimately just shoes.

A man is not his pants. A man is not his shoes. A woman - like the LW - who thinks otherwise probably IS her pants and shoes. Wakey wakey! Time's a wasting! Turn that critical eye inward. Get some new friends - even some with (gasp) uncool shoes and pants and hair - people who pay less attention to their outsides often have the most fascinating insights (not always - but often). Read more - think about what you read. Spend some time learning how to get really good (not competitive) at something - knitting or running or painting or cooking. The process of learning, honing and perfecting some small skill can be very reflective and introspective, if you let it.

Cool isn't something you consume or acquire. It's something you become from the inside out.