#1289: “A potential friend is now an ex, and I don’t know why.”

“Let’s be friends 4-ever” is a wish, not a promise, so it was in the high school yearbook, and so it is at work.

Hello Cap,

I’m so glad I found your blog and this calm voice of reason sorting through a variety of messy situations – made me feel better about this bizarre situation I’ve been in since last year. 

At some level, I just want to pour my heart out to a complete stranger who can assess things objectively, because the situation is so odd, I just don’t think my closest friends will understand. 

So here’s the deal – I am a heterosexual woman. I’ve been married five years to a loving, amazing man who is also my best friend. I’ve had a lot of close friendships with women though – and in many cases, that has skirted into the bounds of love or admiration. I am not physically attracted to woman (i.e. I will find a woman beautiful and be blown away by her but wouldn’t want to really get physical). But mentally and spiritually, some of my deepest connections have been with women. And last year, I connected with one that has just left me pretty dazed and sometimes devastated.

She was a subordinate at work – I was pretty much her direct boss. First couple of years, we rubbed together a bit uneasily – she was tough to work with, I was pretty set in some ideas and on the whole, we didn’t like each other very much. But we soon realised that if we gave each other a bit of space, we worked really well together. Our work styles complemented each other, we could bounce stuff off easily and came up with some great creative solutions (we were in the advertising space). Outside of work, we didn’t have much of a rapport, though I had an inkling that we had a lot of common interests. 

Things changed when we went on a work trip together – and our stilted interactions of the previous years melded into a sort of easy camaraderie. We realised we had a lot of stuff in common, we explored the city we’d visited together and really enjoyed reacting to its various quirks. We also seemed to know instinctively when the other needed space. I gathered she thought I was aloof, she was used to a lot more workplace camaraderie. And so after we came back, I opened up and we started talking about a lot more other things.

A few work drinking sessions including a one on one ‘appraisal’ happened – where we drank and talked about everything under the sun for 5 hours straight without even realising the time; and pretty soon, I knew I was in something close to love. I don’t quite know how to describe the situation – we talked a lot in the office about everything. We liked the same kind of music, the same nerdy franchises, video games (something we bonded over the most), and we really just seemed to understand and get each other’s hopes, passions and aspirations. It was hard maintaining my objectivity as a boss – but the system in the company was pretty flat anyway, so that was manageable. At some level, I felt my life had changed – I wanted to spend all my time with her, because we didn’t just know how to talk, we were also so comfortable just ‘being’ together. I was convinced if we’d met in college (we’re the same age, she also got married around the same time I did), our lives would’ve been completely different. I told my husband – he was largely amused by my predicament and even gave me permission to ‘do something’ with her if I really wanted to (bless him, what a man). The couple of times he met us together post work he admitted we had a ton of chemistry.

Our company started getting into trouble though and I started looking out for a new job. At some level I also felt, if I could get out of the awkwardness of us being boss-subordinate, we could just be friends, equals. Finally, I got another job and quit and told her. She was devastated. I had been priming her for it, but she still didn’t take it too well. Pretty soon after that, she told me she was going to quit too. 

Things started to get awkward though – I’d moved to a stage where I wanted to hang out so badly, I think I became overbearing (I tend to do this). A couple of times when she said no, I took it very badly. I didn’t tell her as such, but my behaviour showed it I think. My farewell was a messy, emotional affair and I got waay too drunk, but I told her how much our working relationship meant to me and how I hoped we would be friends.

We’d wanted to keep working together in some way – and for a month it was nice. We spoke regularly, met quite a few times, tried doing a podcast together (which sucked). And then suddenly, she changed. She stopped responding properly – when I asked to meet or even just ‘supped her, it seemed like she was going through the motions and didn’t really want to engage. This wasn’t a gradual falling out of touch, her behaviour changed almost overnight. Sometimes she was plain rude. I just couldn’t understand what had happened. I knew the workplace had become pretty toxic after I’d left and she was hating it. I came to know another colleague had bad mouthed me to her. So I tried a lot of things – I was curt (she did try sending me conciliatory texts sometimes), I gave her space, I was concerned and sweet, told her I was there if she needed to vent. But things kept moving south. Finally, she did quit and we met a few days after her last day but it was clear our equation had changed. We weren’t in sync. And then lockdown hit, and I felt we both needed time and distance from ourselves and everything to do with our workplace. 

It hasn’t revived though. We’ve had very few conversations since March and most were forced. In one, it felt like we were getting back into our groove but she abruptly stopped replying. At some level, the past 7-8 months have been such a rollercoaster, and she has been so rude at times, I’m not even sure I want to put in the effort to engage any more. But sometimes I also think, man, we just had so much potential. As a person, with some distance from it, I feel I could be less overbearing and more balanced – and this new, calm version of me just really wants to give our friendship a shot. I am jealous of another friend she has who seems a complete idiot, but whom she treats with a lot of affection.

I’ve been trying to let it go. In July, we both lost close family members (found out through her Instagram). I immediately messaged her my condolences – and I knew she’d seen my insta post about my loss too – but she didn’t say anything about that to me at all. I checked up on her one week after that and her replies were mechanical. I really think it is done now, and I just can’t identify with this person she has become (or maybe always was).

I just wish I could get some closure – some understanding of what happened. Was it because I threw her in the deep end at work? Was it something else I did? Is she jealous that I’m a bit more successful and rich, given we’re the same age? Was everything we had just an infatuation? It’s been a year since I quit the job and while I’m largely over things, I still have relapses like today. 

Do help me make sense of it all Cap!


A very confused woman

Dear Very Confused,

To find the answers you seek, start with this sentence of your letter: “She was a subordinate at work – I was pretty much her direct boss.” See also: “We …tried doing a podcast together (which sucked).” ” I knew the workplace had become pretty toxic after I’d left and she was hating it.”

How would you say your friend’s career is going these days? You were her supervisor at work for years, and close work-friends for several months. How would you say her professional growth was during her time with you, and how is that working out for her now? After having you as a boss and a dedicated mentor and friend, did she end up with more skills, a promotion, more opportunities, more money?

Imagine you’re writing a glowing LinkedIn recommendation (which you should do, if you haven’t already, however the friendship shakes out) or speaking about her to someone seeking a reference. What would you say about her work that can position her to do more and better work?

There are close, real, intense friendships that form under pressure and proximity; summer camp, study abroad semesters in college, political campaigns, movie sets, and workplaces that self-describe as “fast-paced” or “work hard, play hard” (so, advertising) are especially prone to them. It’s not weird that some of friendships that form when you’re in a strange pocket universe where you barely have time to see anyone who doesn’t also live there can feel like crushes or be outright crushes, to the point that there’s a let-down when the intensity ends and you’re no longer being carried on that momentum, even if everyone still likes each other fine.

There are also close, real friendships that form across power dynamics – teachers & students, managers & employees –  Mad Men’s Don Draper and Peggy Olson had their weird “you might be the only person who really gets me” kindred spirit thing with its long nights of boozy truths and heads on laps (See: “The Suitcase“). I’d like to imagine that after the show story ended Peggy and Don had lunch now and again, and they probably had fun competing for the same clients and recognizing each other’s words coming over the airwaves over the years, but even in the fanfic their friendship will always be a working one.

This is why, no matter how many times you mention “camaraderie” or explain that, actually, your workplace hierarchy was pretty flat, and no matter how much this lady came to like you as a person, it matters a whole bunch that you. were. her. boss.

You were obsessed with her for her, and for how she fit into your long story about falling almost-in-love with your female friends, whereas she *had to be* a certain amount of invested in you if she wanted to eat. It doesn’t mean that the friendship, the confidences, the camaraderie™ you shared weren’t real — It’s really nice when the person who you have to spend all your time with at work is a person you’d be happy to spend time with anyway! But it also means that it’s incredibly probable that how your former-employee feels about you is inextricable from how she feels about that workplace, her job there, and her career in general. If that stuff is not going well – and it sounds like it’s not – it’s no surprise to me that she would be investing in parts of her life and people in her life who aren’t connected to work, and All The Times My Boss Was So Obsessed With Me Her Amazing Husband Said It Would Be Okay If We Slept Together (Ha, Ha, What A Funny Joke That No Queer Girl Has Ever Heard From A Straight Lady Before) are part of what she needs to forget and block out in order to meet you on equal, neutral ground (if she in fact ever wants to do that).

Hopefully that explains some of what’s happening. Here’s the advice part:

  • This person doesn’t owe you anything, including an explanation for what happened. Accept this, please. You worked together, you left the company, you remained friendly, it’s not unreasonable that the intensity of your interactions would diminish when necessity, power, and proximity did, or in the middle of a global crisis, family loss and grief, and whole swathes of her life that aren’t about you.
  • Dial back the intensity and expectations in any interactions you do have with her. The harder you try to untangle it, the weirder you’re gonna make it. Stop.
  • Stop haunting her social media. Stop messaging her and auditing her reply times and your tone. You’re obsessing, it’s not good for you.
  • Grieve this like a breakup, since it sounds like it feels like one for you. Be nice to yourself, put the attention you are putting into reconciling with this one friend into your marriage, your family, your other friendships, especially friendships with peers (vs. subordinates).
  • If quasi-romantic relationships with women are a serial thing for you, maybe some introspection about your identity is in order. Who knows? Life is long and weird, and people change.
  • You want to be in this person’s life in a positive, rewarding way? Then be a great, supportive ex-boss. Give excellent references when asked, forward job leads and networking opportunities now and again* when you come across them, support and cheerlead her career *without expectation of anything except professional cordiality* and *without making it about yourself.* It’s both the right thing to do and the best chance you have of rescuing something good from this situation when more time has passed.

I hope this helps, I’m sending you very good wishes.

*”Now and again”=Twice a year, max, and if you get no response, stop forever.