Last Updated on August 25, 2023
Last weekend I returned to my hometown for my 30th class reunion. Yup, you read that right. The big 3-0. Have you attended one of your high school reunions? I’ve attended a few and always had a good time, but this one, in particular, was interesting, and I wound up having a major personal revelation.
The day before we left for Wisconsin, I had a therapy session…because, you know, we should all probably be in therapy. Anyhoo, I explained my weekend plans, and she said oh, we’ve never really chatted about your childhood. Srsly lady. Do you really wanna poke that bear? Today?
The Words To Describe Yourself post has probably given you some insight into the world as I see myself, and the Biltmore Country Club post with the Jennys. But to sum up last week’s session in a nutshell, I explained to my therapist that I always considered myself the weird one, boys from my class didn’t date me, I wasn’t asked to prom, and I really didn’t have a core group of friends. I was what you might call “the floater”—the classmate who jumped from group to group. Something I’ve always held animosity towards. By the end of the session, we discussed how tough it was, always told to conform, and how not conforming to the social norm can make you feel rejected…even if you’re doing it to yourself. Ya, it was a lot.
This is me in either my freshman or sophomore year of high school (basing the time off the outfit) circa 1988-ish? Wearing a Cure concert t-shirt, my dad’s old blazer (I think), I sewed vintage lace to the collar and pocket flaps, and my Guess denim mini skirt.
Table of Contents
The Outfit Options
I would text my friend Colleen about outfits leading up to the class reunion. I’ve put on some weight between Covid, throwing out my back in June, a shoulder issue, tendonitis in my Achilles, and hormone changes. Let’s just say I wasn’t feeling the best about how I looked in my clothes. These are the outfit contenders, and I asked my followers on Instagram which one they liked best.
SHOP OPTION #1
Red Dress – this may look familiar – I shared it recently in the Anthropologie sale picks post.
Chanel Earrings – vintage
Proenza Schuler Lunchbox Clutch – Season 2012 – no longer available
SHOP OPTION #2
Black Shirt from GOOP – now only available in white
Red Wide Leg Pants – also shared in my Anthro sale picks post
Chanel Earrings – vintage
Chloe C Double Carry Bag – purchased from Rebag
Miu Miu Mary Jane Pumps – purchased from The Real Real
SHOP OPTION #3
Denim Shorts – presently on sale for 50% off
Gold St. John’s Earrings – vintage
Tom Ford Jennifer Crossbody – purchased from Rebag
Fendi Sandals – no longer available in white
Meanwhile, I recently reconnected with a couple of high school classmates, Emily and Teresa, over Facebook a few months ago (we’ve been sharing music favs back and forth for inspiration), and I also mentioned to them that I was trying to pick out an outfit. Emily said, whatever you wear, I’ll bet it’s awesome and crazy cool. My response was no, I want to look as normal as possible. We are channeling normal, not cool. Sticking to plain and everyday ordinary. Looking at the outfits I chose (see slideshow above), I’m not sure I succeeded in that department.
I arrived at my parent’s house on Friday and met up with Colleen at Balanced Rock Winery to watch my friend Corey’s band, The Blacker Brothers Band play—BTDubs, if you’re ever in Wisconsin, go see them. You won’t regret it. Corey is a genius on guitar. Anyhoo, I wore the denim shorts outfit above and smelled like a foot because of my spray tan. LOL. Totally not feel self-conscious already, right?
Colleen and I popped into the local wine bar after the show, and a few people she knew stopped by the table to say hello. One person asked how long we’ve known each other. He was astonished when we said since the 7th grade—apparently, knowing someone that long is a rarity.
Saturday morning, Colleen texted that she was at the coffee shop on the square with Angie, yet another classmate and I should stop by. Can I say that, looking back, this was the highlight of my entire weekend? We chatted for hours, catching up on what happened between the time gap of high school graduation to now. They’ve both led pretty incredible lives and are strong, independent, beautiful women.
Ladies, you know I love you because out of the three pics you sent, this was the worst of me but the best of you, LOL.
After a woman we didn’t know walked around the block multiple times with a beer in her hand (balls of steal goals, right?), we realized the time and parted ways. I need to take a shower and do some wishful makeup-ing. Ultimately, the red dress prevailed, and I arrived at my reunion solo (The Boy had a huge presentation for work and couldn’t make it). Nervous and completely self-conscious, I opened the door and walked in.
The reunion was fun. The classmates that attended were lovely, and it was fun catching up. Hearing about their lives. One is a scientist. Another is an amazing woodworker. Another a badass cop in Madison.
It was also strange to talk to people who are not on social media. They asked if I was married, had kids, and what I did for a living. I mean, how do you not know these things? I overshare on the internet every single day. Side note, I kinda wish that was me.
Looking back on my 20-year reunion, I thought it was strange that classmates I hadn’t seen in years knew everything about me because of Facebook. But now it’s the reverse effect. Every once in a while, I would stand back and watch my classmates. The same people stuck to their particular cliques, and I floated from group to group. It was just like high school, but this time there was no resentment. Eventually, I made my way home.
After The Reunion
I was on a text chain with Colleen and Angie a few nights ago. We were talking about our lives in high school, and Angie wrote this, “I was just thinking the other day that you were one of the people that I just thought so highly of because you were creative and had the best clothes and the best style and you were such a nice person, you always felt natural and confident.”
I’m sorry, what? Are you remembering the same person? We chatted about how interesting it was that we developed narratives of ourselves in our heads that were completely inaccurate.
Angie thought I didn’t go to prom because I was too cool to attend. She said, “you always hung around the older kids, so I just thought we were not cool enough for you.” Colleen thought that same damn thing. I went on to explain that I didn’t go to prom because no one asked me to go to prom. Well, I take that back, I went, I sat upstairs and watched from afar, wishing I was on the gym floor, then I drove to DJ’s, the underage dance club in Wisconsin Dells.
After I explained how I felt about myself, she said she was shocked at what I was saying about myself. She said, “I don’t want you to think that you are crazy or that your feelings are not valid, but I would bet that 99.9% of people feel the same way I do about you.” Now it was my turn to be shocked.
Queue the tears…the release of the built-up high school drama. Is this how people view me? I admit I have a pretty intense resting bitch face, and I hold up a wall like a pro when I attend parties where I know no one. I can see how that can make me look intimidating. Maybe my ADHD has me forgetting to connect with people, only waiting for them to connect with me—so many revelations.
It has taken me 48 years to realize it was never about what I wore or how I looked. Carrying a fancy purse doesn’t make someone like you more. In fact, it can be more intimidating. Wearing Benetton clothing in high school intimidated Angie. I begged my mom for Benetton clothing, hoping classmates would accept me more. I wish I had learned this earlier because my credit card wouldn’t have gotten such a workout.
Anyhoo, I will be working on me and have a whole lotta material to work with during my next therapy session. I’m also very thankful to have such amazing friends in my life. People who support me and love me for who I am. And if you made it this long, bravo, friend! This was another long hauler, and I’m glad you hung in there and hope this post helped you. I would love it if you left a message in the comment section below.
Read More Of Kyla’s Personal Musings
I took the kids into the city for a little spring break adventure to tour Balthazar Amps and meet Bob Weston.
Ever wonder how House Of Hipsters got its name? I’m spilling the tea here.
In 2020, TikTok diagnosed me with ADHD, not a doctor, TikTok.
I got to chat with my friend high school friend Scott Wostal — he’s an interesting character and I call him my friend.
Holy crap, I’m a One Room Challenge Featured Designer! Check out the room I’m planning to makeover.
Rita
Hi Kyla, this was a lovely, very honest post. I just drove home past a high school in my suburb (I’m in Australia) and they have a lit up board with inspirational quotes for the students and I noticed tonight it had “While you are doubting yourself, remember someone is admiring your strength “. From what you’ve written I feel this quote would have been helpful for your teenage self. I was very similar to you in high school and tell my kids I hung around with the weirdos. And go The Cure.
Kyla Herbes
RitaThat quote is a good one, and I think I need to write it down and stick it to my computer. Thank you soooooo much for reading. Cure fans unite!
Suzi
Hi Kyla! Great post and great reminder to get out of our own heads once in awhile…sometimes it’s a bit scary in there! I was born in WI., moved to Naperville at 3 mos,, moved 5 blocks from Watertower Place, got married 43 years ago and became a Californian.
All this to say I live a bit vicariously through you because I do miss Chicago and surroundings, so you keep me feeling a bit connected and you embody the midwestern humor I adore and it can’t be replicated in any other region in this country!
Gaylene Knowles
All I have to say is your amazing… so humble, vulnerable and because you share from this place we all learn much needed lessons from what you’ve been through. Thank you.
Patrick Weseman
Love the honesty in this post. My graduating class has really never had a formal reunion and we have been out 36 years now.. Even though we all graduated from a school in the San Francisco Bay Area, now everybody lives in all parts of the country.
Any-hoo., it has been strange finding out how many people think I am cool now even though I am the same non-conformist (even more so these days) I was back in the day. Pretty much have always gone my own way and marched to beat of my own drummer.. Now that is lauded by the same people who stayed away from me back in the day. Also, it weird that people want to be my friend on social media these days.
It is what it is.
Kyla Herbes
Patrick WesemanPatrick! You put the biggest smile on my face when you leave a comment. Thank you so much for reading and always returning.
How large was your graduating class in San Fran?
Patrick Weseman
I actually grew up in Hayward which is in the East Bay (across the bridge). My high school was the hood school. I think we started with 400 kids in our freshman year and graduated like 150. There are literally pages in our freshman yearbook of kids that never made it to our senior year for various reasons.