The Friend Who Couldn't See Through the Fog

On Friendship, Loss, and the Fog We Can't Always See Through

[NOTE: This post contains discussion of suicide and self-harm. If you or someone you know is struggling with suicidal thoughts, please reach out for help. In the US, contact the 988 Suicide & Crisis Lifeline by calling or texting 988, or chat online at 988lifeline.org. You are not alone.]

I met Hailey¹ back in 1994, when I first moved into the West Village and was working at Morgan Stanley. She was the first friend I made that wasn't from work and wasn't a carryover from a previous life in Massapequa or Oswego.

We met at some concert at Irving Plaza—she came with someone I worked with, and I went with a friend from work too. Somehow we both missed that our respective friends were using us as decoys so they could hook up. Left to our own devices that night, we became fast friends and attended our fair share of Matzo Balls over those next few years (IYKYK).

Hailey always managed to turn the parties in my respective apartments into a dance party of some sort — Dec., 2002.

Hailey was finishing law school and working part-time at a firm while I was trying to build my career at Morgan Stanley. We'd work long days and then be on the phone nightly for an hour talking about whatever was on our minds. Weekends meant going out together—Hailey definitely attracted the guys and I was the wingman.

There were Thursday nights at Down the Hatch with our growing friend group, movies on summer weekends because theaters were the only places with decent air conditioning. When Hailey passed the bar exam and officially added "Esq." after her name, we celebrated big time—she'd worked so incredibly hard for that moment.

Some of the crew crammed in what is a typical Brooklyn kitchen right before I moved to Seattle with the future hubs.

One night, after I'd cancelled on Hailey a couple of Friday nights in a row because I was exhausted from work, she chastised me. It put her in a bind to find other plans at the last minute, she said. Remember, this was the '90s—no mobile phones or texting to easily reorganize on the fly. So the next time we made plans, tired or not, I pushed through. We were at dinner and I was so exhausted that I face-planted into my mashed potatoes. No joke. It actually happened.

“But Jill, were you so tired that you fell asleep in your mashed potatoes?" became our running joke.

There were lots of shenanigans with the two of us. One time, these two guys were talking to us in a bar and one of them was clearly trying to impress Hailey. And like any good 'partners in crime', we had a code on when we were not interested in the person(s) chatting us up. So he says, "Oh, I have this great story, do you want to hear it?"

I don't know what came over me, but I just dead panned "no." And the guy started to talk and then looked stunned. Simultaneously, Hailey spit up her drink. Needless to say if there was any interest from these guys, it was now gone. Mission accomplished. It's a vivid memory that makes me both laugh and feel sad as I type this.

Hailey joked that even as a native New Yorker, she couldn't navigate south of 14th Street, where I lived. It took her 15 or 20 tries to figure out how to get to my apartment—two blocks from the subway. She'd laugh about how book smart she was (yes, she was VERY intelligent) but had zero common sense, especially when it came to directions. Once, when I asked her to bring cave-aged gruyere to a dinner party, she asked the cheesemonger at Murray’s for ‘stone-aged gruyere.’ The confused look he gave her became another one of our many inside jokes.

Our friendship continued to evolve. When Hailey met her future husband, our dynamic didn't miss a beat. The friend group expanded. We took swing dancing classes, tried salsa, attempted cooking classes (though Hailey never really took to those) and went clubbing. Our music tastes differed - she loved club music and hip hop, and I was stuck in the 80s. There were dinner parties in our cramped apartments, lots of laughs, great times with some mischief thrown in for good measure.

As the '90s rolled into the 2000s, Hailey got married. I was in the wedding and did all the things. Then 9/11 happened, which had a profound impact on all of us. A few months later, I met the future hubs on vacation in Greece, and soon after that, I moved to Seattle—with no idea I'd still be here almost 23 years later.

I’m guessing there were some people cooling off on the fire escape at this point. That’s not really a thing in Seattle.

Initially, I was coming back to New York four or five times a year, so our friendship didn't suffer immediately. But things changed around the time the hubs and I got married. We planned a destination wedding well in advance to give people notice. Hailey was strangely quiet about her plans, which was out of character. Even at my bachelorette party six weeks before, she was cagey about when she was flying out, where she was staying and how she and her husband would get there since they didn't drive (I was trying to sort out shuttle options for them). I sensed something was up.

Two weeks before the wedding, Hailey left me a voice mail to tell me she wasn’t coming. She didn't feel comfortable being away for the Friday before Memorial Day weekend, she said. Given the depth of our friendship, I was devastated. She promised to make it up to me, but I didn't understand how you do that at such a big moment. The trust felt broken, and I started to pull back. That change coincided with spending more time with my family as my parents got older and with nephews and nieces entering the picture.

We addressed it briefly—Hailey said she didn't feel comfortable pulling away from her law firm for even one day despite her tenure. It seemed hollow, especially given how she'd always expected loyalty and commitment from me. We could agree to disagree, but something fundamental had shifted for me.

When social media emerged, we were "friends" on Facebook, but I had moved on. I was building my life in Seattle with the hubs and, processing the loss of that friendship while making new ones. A few years later, I left social media entirely for seven years because I felt it was toxic. When I started Go Long, I had to return—that's where my target demographic lives. Spoiler alert: it's still a toxic cesspool.

But through that 2nd foray on to Facebook, Hailey and I reconnected. She knew the hubs and I traveled, so she'd ask for recommendations over DM. Then in January, she asked to chat. It was the first real conversation we'd had in almost 18 years. We reminisced and laughed about the past while also catching up on the present. Her laugh hadn’t changed and it made me smile not knowing what was to come a few months later.

Hailey was dealing with a rough work situation but nothing that seemed out of the ordinary given market conditions unfortunately. She was working with a life coach and spending time doing creative writing.

Hailey was picking my brain about leaving corporate, particularly about starting Go Long. I told her it was more than just the work piece—it was about finding purpose through taking care of myself, getting outside, spending time with the hubs, friends, and family. Yes, working on something meaningful is fulfilling, but the point was incorporating activities outside of work that gave life purpose.

Looking back on that call, I remember her looking tentative and scared. She was taking notes about what I was saying. I told her she could do this—she'd endured harder things when we were younger.

When I found out that she lost her battle with depression, what I heard from mutual friends was that she'd lost hope for her future. She was seeing a mental health professional at this point. That this happened on 9/11, a day already heavy with loss and grief for all of us who were there on that awful day, felt like this was well planned.

It makes me profoundly sad that Hailey reached a place where the loss of hope felt significantly heavier than any optimism for what could come next, even while receiving increased mental health assistance.

Hailey never felt good enough in various aspects of her life and constantly compared herself to others. There's imposter syndrome, which many of us experience, and then there's something deeper. After being forced out of her firm after 27+ years, her identity as a lawyer felt shattered. It wasn't about money—it was about how she could possibly start something new. But putting the pieces together is harder than it seems when you're limited by what someone chooses to share.

It's difficult to know when someone is just down on themselves versus dealing with something more serious. In my experience, when someone is determined to end their pain, you're not going to get in their way. Hailey conceded victory to her opponent, in this case depression, and it's our loss.

I found out on Friday late afternoon and spent Saturday morning out paddle boarding. It was good to have an hour to continue processing this in solitude. This was a person who was my "ride or die" for the better part of 12 years. In one sense, I mourned the loss of our friendship back in 2006. But this obviously has brought a different layer of grief that's hard to articulate—something more visceral and final.

Is it truly the full closure of an era in my life that was so formative? I'm unsure.

My feelings vacillate between sadness, tragedy, and bafflement. The situation is tragic because Hailey was surrounded by people who loved and cared about her, but that she couldn't cut through the fog. She had so much going for her, but she couldn't see past her current circumstances to imagine hope and joy on the other side.

The upside of this tragedy is that I've reconnected with a number of people I hadn't been in touch with for over a decade or more. We've shared our sorrow, but also found ourselves laughing about the hijinks we got ourselves into all those years ago. Maybe not Broad City level, but definitely some questionable life choices that seem both ridiculous and precious now.

September is National Suicide Prevention Month. Use this opportunity to reach out to someone you haven't connected with in a while. Take a break from social media. Connect IRL. While I'm under no illusions that I could have prevented what happened, the whole thing makes me profoundly sad that a brilliant, funny and beautiful woman couldn't see through the fog that clarity might be waiting on the other side.

Hailey, I hope you found the peace you were looking for.

You were loved more than you knew and you will be missed.

1. Name changed for privacy reasons.