I have a hidden folder on my laptop that is labeled “Letters I Should Have Sent.”  I created this folder in 2003, after returning to the US from living abroad, in Ireland and then in Luxembourg, for 3 years.  I was unhappy with many aspects of my life and, at the time, it felt like a simple way to harmlessly get out a lot of the frustration I felt.   That year I wrote letters to my new boss, who I found to be very untrustworthy after working with her for only 3 months.  To the woman who I had rented a home from in Luxembourg, who was trying to sue me for unspecified damages that I knew I had not incurred. Most of that letter was written in broken French, and ended with a lot of good old American cuss words. There were letters to friends who treated me differently upon my return.  To the friends I had left behind and sorely missed, the cities I feared I would never see again.  To my family for . . . well, for all the reasons our family upsets us from time to time.

Over a 15 year period, I have written 107 letters.   I’ve moved that folder from a few different laptops over the years, and I have deleted a few rough drafts, unfinished thoughts.   Most of them, I spent a lot of time on, drafted them and then carefully re-wrote passages for maximum impact.  Some of them were very short and unimportant, and sometimes, quite funny.

The letter that makes me laugh the most was written in 2012 to one of my then roommates (an ill-advised ‘favor’ to my boyfriend of the time to let his best friend live with us).  It was written, I can see, at 2:47 a.m. on a Sunday morning, and simply says “Dear Jesse – F*** You!!!”  I am assuming it was written in response to one of his many episodes of night time terrors where he did things like pop the screen out of the window in his bedroom, jump out, run around in the yard, screaming, in his underwear until he finally woke himself up, and then sheepishly rang the doorbell, which I would answer with both concern and anger.  He never apologized for those episodes in the moment, just slunk, shame-faced, back to his bedroom.  Often, we’d end up repeating the episode in a few hours.  This happened quite frequently that year.  I’m sure it was a result of all the stress in his life at the time, but often, I had little patience for it.  On this night, apparently, I had none. They were very scary incidents at the time, but now I can remember them with laughter, just because of the sheer absurdity.  I haven’t spoken to him in years.  I hope he sought treatment and has found some peace.

Some of them were extremely painful to me at the time.  There were the letters I wrote to my partner’s lovers, and, in one particularly emotional moment, the letter I wrote to one of those women’s husband, who was completely unaware (I believe) of the affair.  That one I nearly sent; I had printed it out, addressed it, put a stamp on it, and it was ready to go.  It sat for weeks on my desk. I ultimately couldn’t send it.  I could not stop thinking about the damage that would be done to the husband, and possibly to their children.  To their extended families.  In time, my life and my relationship could be rebuilt.  I wasn’t willing to be the one to ruin more lives.

There were letters to my ex-boyfriend’s mother, who badly abused my generosity, constantly lied to me and manipulated me, and who eventually owed me more than $6,000, all promised back to me at various points over our 4 year relationship, and which I never saw again.

I had a whole series of letters from 2010 – 2013 to my then boyfriend for all his horrible behavior.   There was a lot of it.  I do not know why I didn’t end it with him sooner.  I consider my relationship with him to be my biggest life mistake and part of my first mid-life crisis.  Sometimes I re-read those letters, and shake my head in disbelief and anger.   Those are the semi-lost years; I can never get them back but I can always remember them and study them as a reminder of what kind of behavior and relationship to never accept again.

One standout letter, written in 2013, was to my department VP at the time, a man that I knew to be ‘ethically challenged,” and one of the first people I thought of when the #metoo movement began.   It very strongly seemed that the only way someone who worked underneath him could get a raise or promotion was to . . . well, work ‘underneath’ him.  Intimately.  He judged his staff by their physical assets and was constantly embroiled in relationship issues because (it would appear) of his inability to keep his privates private.  I heard stories from colleagues and saw some photos, texts, and videos he had shared with them.  Even though I didn’t report directly to him (I worked for one of his direct reports) I was never going to advance much farther there.   I stayed 2 years longer in that job than I should have until I found the strength to leave and find a much better company.  I have since heard that his antics have cost him dearly – promotions, relationships, friendships.  I hope it has taught him a lesson. I fear he has not learned it.

I think the most important letter was to my mother, who we lost far too soon in 2005.  I was completely unprepared to lose her, and I went through a period of roughly 20 months of the worst depression of my life after she passed.  Then one morning, in May 2007, I woke up and thought – oh, there I am.  I felt better.  More like myself.  I knew I had finally come out the other side.  I was still sad, but I was ready to move forward.  Early that morning I sat on my back deck with a cup of coffee, watching the spring birds, and I wrote her a long letter.  It took me 2 hours and waterfalls of tears to write.  I told her how much I missed her, how much she had meant to me, what a profoundly positive impact she had on my life.  I wish I would have written it and given to her before she died.

When my dad passed away in 2013, I tried to write a letter, but it never came together.  There is a partial letter there, which is a lot like the relationship I had with him; full of half-finished sentences, paragraphs I do not know how to end, feelings I am still unable to express.

In many ways, the letters have acted as a journal for me, reliving some key moments and the emotional responses that often followed.  The things I should have said.  The things I wish I hadn’t said.  In the upsetting episodes of our lives, we are never our best in the heat of the moment.  Often I tried to respond in these situations in a way that I hoped showed that I was kind, helpful, giving, supportive.  In reality I can now see that I was often actually scared.  Full of angst, anger, sadness, fear, guilt, shame, worry.  Unable to set boundaries, unable to see I deserved more.  I wrote these letters because I needed to get it all out, and find a momentary sanctuary.  In many of these scenarios – I should have sent the letter.  Or, at the very least, opened up to the person or people involved and shared with them how I truly felt.

Over the years I’ve gotten better at expressing myself safely, honestly, and have been more deliberate and firm in setting my boundaries.  I still need to do more work there, but I feel like I can better see my own worth, and acknowledge when bad behavior is not acceptable.  I’m sharing more of the positive moments too, telling people how much they mean to me now, quicker to thank people, more apt to get involved in social events where I can connect.  I’m sure I will keep writing letters, but this time, if the tone is overall negative or fear based, I will sit down with each one and figure out what really needs to be said.  And then find the courage to say it.


Virginia Addis is a Project Manager by day and a podcast enthusiast by night.   She lives in a historic home in Franklin Park with her 2 wonderful dogs, and she loves to explore the little known gems (parks, buildings, artists, restaurants, stores) of Columbus.  She is currently developing her own podcast, which will mainly focus on women’s issues as well as life in Columbus, and which she plans to launch in August this year.