Chapter 6: Girls' Night

At 22, I finally had my first opportunity to go on a girls' night out with cool older women. Surely I wouldn't screw it up.

For those of you who are new: welcome! In case this format looks unfamiliar to you, this is Chapter 6 of my book, Will There Be Free Food?, a series for subscribers. A chapter is released every Tuesday! All the stories are true—they follow 20-something CHH working in the San Francisco startup scene as an OCD-afflicted, socially inept, young married lady. I like to think they’re pretty funny. Stay tuned—there are many chapters coming up. The best is yet to come!!!

I met Jessica after my feet gave out at the Union Street Fair in San Francisco, having reached a level of wear and tear I can only describe as “mangled.” I was wearing five-inch wooden platform heels, not anticipating that I would be standing, walking and drinking copious amounts of warm vodka for at least five hours. Jessica, a cool older girl (I was twenty-one, she was twenty-seven) hung out with me inside her mostly empty office building while I tried to bandage my feet up with cocktail napkins. 

I don’t remember what we talked about, but I remember that she was one of the first women I met in San Francisco who hadn’t immediately given me the side-eye for wearing a low-cut tank top over a push-up bra with water-filled padding. I knew it sounded obnoxious to say or even think that other women had negative reactions to my aesthetic, and maybe it was a bit of a self-fulfilling prophecy, but it really did seem like my Kardashian club rat fashion era was especially alienating to other women. Generally, my boyfriend Nick liked my clothes, although sometimes it was even too much for him, like when we went to a Stanford tailgate to hang out with some of our friends who were Stanford alums, and I showed up in a blue and yellow corset with low-rise skinny jeans and stripper heels. To make matters worse: yellow and blue were the colors of the opposing team. Nick quickly rushed me to the Stanford gift shop to buy me a giant Stanford T-shirt.

That day at the Union Street Fair, I was still in college, usually living across the country, and was only there to visit Nick, who had graduated before me and moved out to San Francisco for work. Nick knew Jessica through friends. When I arrived in San Francisco that week, I existed in my Forever 21 neon magenta bodycon dresses in a sea of Patagonia vests and dirty looks. I knew it wouldn’t be hard to alter my attire to fit in, but I didn’t want to. I hated the anti-fashion component of being a woman in San Francisco, and as much as I wanted people to like me, I had hope that I could accomplish this without changing my wardrobe. I kept expecting Jessica to say something about how out of place I looked, or even just ask me if I was cold. (I was.) But she didn’t. She was kind, she was funny, and she seemed to like me.

I shouldn’t have been so shocked that Jessica met the low bar of behaving like a normal person, but being extremely unhinged myself, I tended not to assume the best of people. I got threatened and jealous easily, so why wouldn’t she? Perhaps Jessica’s accepting and calm demeanor came from the fact that she didn’t see my provocative choice of clothing as a threat to her own attractiveness. Perhaps it was because I was safely partnered, but I think it had more to do with the fact that Jessica didn’t place a lot of self worth in how she dressed or primped. As we continued talking, I realized she valued her friendships, personal development and career much more, and as someone who regularly measured my waist/hip ratio and stored it in an Excel pivot table, Jessica’s attitude intrigued me. She even read books.

Jessica was an accomplished advertising executive. I looked up her job on Glassdoor after meeting her to discover she made at least $100K, which to me might as well have been $1M. As for her social circle, we ran into seemingly two hundred people at the Union Street Fair that day who were close to Jessica, all of whom seemed incredibly cool and mature. I went back to college and didn’t think much about Jessica, but when I graduated and moved to San Francisco permanently, she appeared on my radar again when Nick mentioned I should text her. I did, and we met up at a few parties. She might have been grown-up and successful, but she loved nightlife just as much as I did, and she was socially connected enough to always have a fun place to go.

I was about to celebrate my twenty-second birthday. I had always struggled to get people to attend my birthday parties, even as a child, so I wasn’t sure why I thought I’d be able to amass a group in a new city where I quite literally had no friends, but I attempted nonetheless. I told Nick to invite his pals–whoever liked me enough to tolerate me for a night–to a place called Vortex which had already become my favorite club in the city. We knew the bouncer at Vortex, who always let us cut the line and would funnel us through the back of the club like the club scene in Goodfellas. We never once actually bought anything at Vortex.

 Nick encouraged me to invite Jessica, even though it was unlikely she would come on such short notice. And much to my surprise, she came, nonchalantly wearing that same outfit she wore when we met–teal jacket and flats with her hair in a ponytail. This successful, grown-up woman with lots of her own friends attended a last-minute birthday party of an insane twenty-two-year-old in a Wet Seal bandage dress. She even told me she hated Vortex, so she had come specifically because she wanted to see me. 

I had no idea what she liked about me. I got the sense that I was a bit of a  novelty for her, but not in a way that felt predatory or mean. I just for the life of me couldn’t figure out what she was getting out of this friendship. Not only did she have a great career, but she had her own well-established social circle, the kind of circle I always dreamed of having, full of similarly grown-up women who I feared would ask her why the hell she wanted to hang out with me. She had a social calendar that seemed incredibly full, and yet she was making room for me.

After we had been friends for about six months, Jessica invited me on a girls’ night out with the rest of her friend group. This was simply not something I did–I was glued to Nick. Two years of cross-country long distance made us extremely codependent, hoarding time with each other as if we were starving island castaways hoarding food after being rescued. Any minute I spent without him felt like a waste, but Nick encouraged me to go. 

I couldn’t tell how much of my anxiety was about spending a night away from Nick, or about how unlikely it was that I would pass the Socially Acceptable test with all of Jessica’s friends, without Nick to console me if I failed.