A Letter to my Past Girlfriend

Before you start reading, understand that I’m not a reliable narrator. This is difficult for me to come to terms with, as someone who prizes facts and objectivity. But so much of what I’m going to write about can’t be quantified because it’s part of my inner world, which always has a distorted view of reality. Though you are probably the best equipped person on the planet to understand those distortions.

I decided to write this to help me process my emotions from the break up and use it as a way of healing. I think there’s something about sharing with other people and letting them know what’s going on with me that I find very cathartic. Even though it’s been over 7 months since we officially ended things, I still find myself thinking of you from time to time and having feelings of loneliness. Overall people have said I’ve been handling things well, and it’s hard for me to disagree with them. I’ve been coding, going out with friends, traveling, eating right and staying fit, applying to jobs and writing a lot. At the same time, I think the bar for how people handle break ups is set pretty low. I’ve still got some things I wanted to get off my chest and writing is the best way I know how. Hopefully my message is clear enough, because writing this felt completely disjointed and I couldn’t have prepared for the emotional roller coaster this ended up being. No idea why I thought this was going to be easy… But that’s hindsight for you.

It’s funny, I remember we used to write letters to each other during special occasions. I still have them all, somewhere. I haven’t read them in a while. Hopefully I’ve become a better writer since then, because I’ve definitely been practicing a lot. I always worried when I would write one, that I couldn’t make it as heartfelt as you made yours. I felt cheesy. How do I convey how I feel in a way that flows through the reader? How can I really make someone feel how I feel with a few hundred words on a page? It’s taken me some time to be able to pour my heart out on the page like this.

Something happened during a drive down to the South Bay last week. Maybe my brain was primed because I was feeling nervous and overwhelmed by the job hunt, and driving by where you work (or used to work) triggered memories of you. I’m pretty sure the queasiness I was feeling was literally the feeling of being lovesick; my mind going through withdrawals. It’s not the first time I’ve had those feelings, but I was hit unusually hard by them this time. I guess that’s what prompted me to write this thing.

Okay enough rambling. Why don’t I just get straight to the point.


I miss your touch. Your soft feminine texture and temperature. I loved lying next to you in bed in the morning, waking up next to you and taking silly naked selfies. You always needed more sleep than I did. I miss that soft feminine energy in my life, and I didn’t know how much I enjoyed it until it was gone. I didn’t know how good life could be when I shared it with another person, and I worry sometimes I won’t be able to find it again with anyone else. Maybe Passenger was right: ‘You only know you love her when you let her go.’

I think it’s because our brains can’t remember the good times we haven’t had with someone we haven’t met yet. That’s why it’s difficult for me to look ahead at times like this. It took a long time to build up what we had, and it’s difficult for me to imagine having anything else with anyone else. I think this is the reason some people can’t stay broken up, and they go through cycles of breaking up and getting back together. They stick to what they know, because they can’t envision a future with anyone else.

It’s weird, all the bad memories seem to have faded with time. For some reason most of them seem to have happened in a car, usually mine (what is it about road trips that brings out the worst in people?). I don’t really remember the content of most of our fights and usually I can’t even seem to figure out what we were fighting about. I just have some vague recollection of feeling frustrated and disconnected. But that feeling always seemed to pass very quickly, and we’d be back in sync in almost no time. Even the word ‘fight’ seems like an overstatement now. They were more like disagreements that usually stemmed from one of us not communicating our needs or wants clearly to the other.

I also seem to remember a lot of tender moments I didn’t necessarily think were super memorable at the time. Like I remember when you were sick one time and I made you tea with honey, which we spiked with Jack Daniels, and then walking around the park. Not the best time of our lives; it was uncomfortably cold and I think you got me sick and had to take care of me the next week. But it was a moment of genuine connection, where you were happy to be with me and I was happy to be with you and take care of you. And I could see the love in your eyes.

So much love.

It was all the little moments like those that made the whole relationship worth it. I guess this is the lens of hindsight.


There are two things at the moment though that are causing me a lot of pain, and that I feel very ashamed of.

First, I could have been a better boyfriend. I was too self-absorbed, and I still am to a certain extent. During the relationship that meant I couldn’t give you everything you needed. Reassurance, stability, certainty. What you got instead was disorganization, apathy and ambivalence. You met me at a time when I felt lost and though you helped me grow SO much in the three years we were together I didn’t manage get a clear enough picture of the man I wanted to be. But you deserved better than what I could give you. A lot better. And I really do hope you get it, and more, with your next boyfriend.

Second, I feel guilty because I feel like I got more out of the relationship than you did. I feel like I used you, even though that was never my intention. Like I said before, this relationship helped me grow up. It was a place I could retreat to during dark times. You were my best friend, and you understood me better than anyone else, including my parents or brother. You put so much hard work and patience into helping me grow as a person and get past my demons. I will forever be in your debt, but I worry that all you got from me was just more baggage, wasted time, and a broken heart. I want to believe that you got something more out of the relationship. I hope that I left you better than I found you, because you definitely did that for me.

Going forward there is still plenty I need to work on. I need to learn to be more comfortable by myself, before I can include anyone else in my life again. I need to learn how to have self-esteem and not need to seek external validation. And this past year has been great for that. I’ve been much more focused, and have had a lot of time to myself to think and just be alone. I’ve been learning to love, forgive and take care of myself. And I mean in every sense, not just emotionally. I’ve been trying to truly understand what it means for there to be a world beyond my own mind that I’m not the center of. It seems so obvious that it should go without saying, but I’ve see too many supposed “grown-ups” lately who are so emotionally stunted by their childhoods that they lack the self-awareness to see how childishly they act and why people treat them accordingly.


We both faced serious challenges in our personal lives when we first got together and throughout our relationship. Some of them were external forces, like college stresses, finding jobs and careers, our parents divorces, or family health problems. All those things definitely impacted me and my outlook on life. They made me question what was truly important in life and they shaped my adult worldview.

Other problems were internal. I struggled to be honest with myself about how I felt about you. I had no reference point for this kind of relationship before you. And part of the struggle early on in our relationship that ended up weighing on us is that I played games with your heart. I didn’t know what to do with all the new attention and validation.

Somehow, through it all, we managed to still have some amazing and beautiful times together. Trips to Mexico, Tahoe, Camping, Napa, LA. We leaned on each other for support, and helped each other stay sane. We were a safe space when the whole world felt hostile towards us, and I sometimes wonder how I would have made it through those three years if it hadn’t been for you.

Our relationship taught me that we are both way stronger than we look on the outside. For all the chaos, all the mess in our lives, we’re both not only surviving now but thriving and continuing to move forward. And I’ve always admired how much better you were at it than me.

One of the lessons that the chaos also taught me is that life seems to throw a lot of traps and temptations in our way. Empty promises and fantasies that have lead so many people around me into misery. And there are patterns that seem to repeat themselves over generations that need to be broken. Cheating, lying, manipulation, egomania. People become slaves to their baser instincts and think they are somehow free when in reality they are making themselves and others miserable.

There are times when I don’t know what the right path is, but I trust my gut and go where I can find meaningful connections with other people. You taught me that. You taught me what is possible with another person, and it’s hard to forget that lesson. Hopefully I’ll find something like what we had one day. And if I’m lucky I will be worthy of it and able to appreciate it fully.


I’ve talked a lot about what this letter is. Now I want to say a few words about what it isn’t.

This isn’t an attempt to get back together. Deep down, I still think we made the right choice to end things. The relationship was starting to hold us both back, as hard as that is to admit. We both made mistakes, no one is perfect after all. But I don’t see it as a failure. The only relationship that’s truly a failure is one that lasts longer than it should.

I also want to acknowledge the reality of social media and the internet in general. I know there’s a decent chance either you or your boyfriend might actually read this at some point. I’m okay with that, and hope you are too. In the spirit of openness, I’d rather you understand where I’m at in life by reading this than through direct communication or through a newsfeed.

Because I think the problem with Facebook and Instagram stalking it can create unrealistic stories about a person’s life. You still pop up in my feeds, and I’d be lying if I said I didn’t feel a bit of sadness every time I’m reminded of you. But I also realize it’s such an incomplete picture. I have good days and bad days, but those aren’t necessarily captured (though I did just post a picture of my bad hair day to try to make up for it). I have days where being single brings me a sense of freedom and ease, and I’m able to learn things about myself more clearly than I would have had I been in a relationship. There are others where I deeply miss having intimacy in my life. Like anything, there are pros and cons.

Also, one of the traps that people seem to fall into on social media is posting things with the intent of making their ex jealous, or to show off how well they are doing without him or her. I just wanted you to know that I’m mindful of this, and that has never been or will be my intention. You really do seem happy in your new relationship, and I would never want to get in the way your happiness.


Life is long and strange. I have no idea if our paths will cross again, or whether that’s even what’s best for us. But I’m still a friend. Someone who loves you and who you can trust. I want you to go forward and be happy. Be with someone who makes you smile; someone who makes you whole. Someone better than me. Find happiness, make the life you want to make for yourself, and surround yourself with the people you love and who love you most. Hopefully you got something meaningful out of our relationship that will help you in your journey. Something you can take forward with you. A piece of me, that helps you, that you can make part of yourself.

Because the part of you that’s still with me carries me forward every single day.

With Love,

Your Past Boyfriend