Should I send these emails to my estranged friends?
I've been agonizing over this for a while.
This story is really long, and I'm sorry.
Back in 2023, I moved to a new city to work at a new startup owned by my friends of 15 years who are husband and wife. Basically, on paper she is president and owner and CEO, but they both make business decisions.
They were open a few months, working to get their business in motion. I then joined the team fresh out of a completely different industry (went from a 7 year desk job to a physical labor position) and I struggled. 10 days later, I got fired after I posted on social media, venting about a work situation that I was having trouble with (not a complaint about the owners, or the business, more just about myself), and I was connected on social media with people who were clients of the business. It was a foolish and absolutely stupid lapse in judgement, one I might normally have not made.
Back in 2022, I had a relatively minor, but very real ischemic stroke on the left side of my brain that regulates movement, speech, emotional control, and impulse control (my lower basal ganglia). I regained my speech clarity and movement fairly quickly, but time has granted me the ability to look back and see that I may have been a little more brain damaged than I realized. I made a series of stupid decisions: (sure, I'll move 1500 miles and absolutely max all of my credit hands to do it on short notice! Sure, I'll admit to my friend and boss that I was late for work and ran 118mph through downtown. Sure, I'll post on social media that I damaged a piece of our clients property). Just bad decisions all around without having the ability to think "This is a dumb-ass thing to do. Don't do it."
Anyway, I got marched into the office and terminated. Told they needed to protect their brand and new business. I was given my last check. Loaded up my tools and did the walk of shame. They never said anything to me as I walked by. I did my best to vaporize. Deleted and blocked everybody on social media. A month later, I moved out of state back home.
Despite the fact I knew it was business and my own fault, I was angry and upset.
It's been 3.5 years now and I am over it. I have been for a while. About a year and a half ago, I wrote an email to the husband basically telling him that I knew it wasn't personal. Apologized. I don't know if he ever got it, I never heard back. I texted his old number about 6 months later after I heard a guy we both knew had died of cancer. Didn't hear back.
Maybe that should be my clue, now that I type it out. But I wish I could get some kind of acknowledgement, even if it's a great big middle finger.
So I've written both of these emails, one to him, one to her. Let me know what you think.
The first email to her:
"Hi [wife],
I am writing to say hello, and to also try and clear the air on things. I had written to [husband] a while ago. I didn't hear anything back from him, so I wasn't sure if he had even seen the email.
Realistically, the email I wrote to him really needed to be sent to you as well.
I want you to know how sorry I am for the way things went down with me, and us, and [their business]. I have maybe some reasons I wasn't functioning normally, mostly due the stroke I had in 2022... but ultimately no excuses. The fact of the matter is the responsibility for all of it rests entirely on my shoulders.
I really just hope that my poor actions and mistakes didn't damage the reputation of [their business]. And if they did, I truly hope any adverse effects were short lived.
Honestly, I miss you and [husband]. I miss your insight, and the conversations we had, and your friendship.
That being said, if you guys have moved on, and would rather not hear from me, that's absolutely fair, and I won't bother you again.
This whole ordeal has been weighing pretty heavily on my mind the last couple of years and I just needed to get it out into the open to you.
Either way, I want you to know that I do hope things are going well for [their business], and that things are going great with you and [husband], and [their young adult kids].
Take care."
The second email, to him.
"Hi [husband],
It's been a while, and I just wanted to reach out and say hello.
I know things didn't exactly end well between me and us, and [the business]. It was a hard pill to swallow for a long time, but I've long since come to terms with it.
The past has been weighing pretty heavily on my mind lately. I have written and re-written this email no less than a dozen times trying to make it sound right, but I don't know if I'll ever get it completely right.
If you don't care to hear from me, I can accept that. But I want you to know that I really did enjoy our banter, and your insight. Ultimately, I miss my friend. And that's what this email boils down to. If you've moved on, that's completely fair, and I'll leave it alone.
Either way, I want you to know that I hope things are going well with [the business]. Most importantly, I do truly hope things are going great with you, [wife] and [their young adult kids].
Take it easy.
I probably just need to let sleeping dogs lie.
Posted Jun 29, 2026, 11:28 PM UTC