letters from: reaching out to the past

Jan 15, 2025

cozy advice on: when is it okay to apologize to someone from the past?

Today I’ll be answering a question about what to do when we want to reach out to people in our past. This is pulled from r/advice on Reddit. Please submit your questions, and I will answer those as well!

If you would like to ask your own question, please use this form to do so!

Here is what the OP posted:

I'm at a crossroads burdened by past mistakes and unsure on where to move on in my life. I'm 27, and while that is young it's also 5 years after college. Unfortunately, this will likely be a long message so I'll add a TLDR... I am stuck in an unrequited love situation and at a point in my career where I want to move to a new city and a different job. While my love life is one of the main reasons why I'm making this post, it's primarily my existential crisis that's driving this.
I'm at a point in my life where I realized that I need to start 'living' because I realized I only have one life. The sad truth of getting older and not realizing it when young like many others. I'm currently mentally exhausted because of my existential crisis and overthinking. While I am 'living' in the sense of travelling, hanging out with people, hobbies, I don't want to live life with regrets.
My question is: I want to move cities, but I can't decide where because of an ex I still have a crush on. I want to express my feelings to her because I don't want to live life thinking "What if?". It's not just her though, I want to tell my friends sorry for things I've done in the past, but I'm scared of people overreacting wondering "Are you ok?" or "That's a little much" resulting in me being outcasted. Even though I should live life, would I be trauma dumping or is it ok to take a leap of faith and let them judge me for my attempt to reconcile.

Because this is a Reddit post, and not from a letter writer, I decided to omit the longer part of this question. I think this question speaks volumes and probably applies to a lot of people – I know that I deeply relate.

I am on the cusp of turning 27, and I can relate to having regrets like this.

When I went to college at 18, I was a mess.

I had held myself together in high school. I was an overachieving perfectionist who was in every club and organization in the school (except for Future Farmers of America because I was not aiming to be a future farmer), I was a cheerleader, and I graduated high school with an Associate’s degree from our local university (shout out to WNMU). And this was in an area that didn’t have the programs they do now, where you are guided through how to do this. I figured out everything on my own, and the purpose was to have as good of a chance as possible to leave.

I was still an overachiever when I got to college. I took 18 credit hours, worked 20-30 hours a week, had internships, and did theater so that I could make sure I had a job lined up when I graduated. I still had the drive in me that pushed me to work as hard as I could, out of fear that I would fall behind.

This may contain: a woman sitting in a bathtub with her arms crossed — me at 18 in the shared dorm bathtub, drunk, high, and crying, but def not looking as cute as miss swift

At this time, I was also dealing with the emergence of PTSD symptoms that came from my childhood. Now that I no longer lived with my mother or in my hometown, it started bubbling to the surface. In my second year of college, I started therapy again (I had been in therapy at 16 – 18 for SA in high school). It helped, but at the beginning, therapy was like a Band-Aid on a gaping wound. One hour a week couldn’t fix 19 years of repression.

I smoked weed and drank alcohol often and to excess. I slept with a lot of people who I shouldn’t have. I wasn’t a good friend. I wanted to be! I just was not someone who could maintain healthy relationships at that time in my life. I slept with my best friend’s crush for three months and kept it a secret the whole time. I had a love triangle with my roommate and her gay awakening who was also someone I was interested in and talking to (oh, and I was also in love with said roommate). I then had a love square with this crush’s friend. I would ghost friends, sometimes on purpose, sometimes on accident. I would melt down crying in the dining hall. I asked to cheat off my classmates in my honor’s statistics class. I would drink vodka in a coffee cup at work.

I could probably go on and find more examples of the kind of state I was in, but I think I have divulged enough (perhaps too much) to tell you that I was a mess.

So, I understand the feeling of living with regrets.

There is a side of me that so badly wants to show all those people from my past the person I have become and keep becoming. I don’t think I am anywhere near healed (no one is) and I am not without my flaws. But as a whole, I think I’m a pretty grounded, levelheaded, sober person now. Sometimes I say things that I wish I didn’t say, or handle conflict in ways I wish I could re-do, but in general, I’m so much more stable than I was when people from that time of my life knew me.

I want them to know the new me so badly. Not even because I want a relationship with them. Because I want them to see the ways that I have changed. I want them to see the ways that I am better than I used to be.

And, sometimes, that actually isn’t helpful to anyone.

Sometimes it is.

To reach out or not to reach out? As a Pisces that resonates a little too much with Adele’s Hello, I understand this urge. I have sent a great many apology messages in my time. Sometimes, they were very well received. And sometimes, I ended up being blocked. Which, honestly, is good for them.

Here are some things to consider if you want to reach out:

How did you leave things? If things ended pretty amicably or just drifted apart, then I would venture to say a reach-out might be appropriate. Especially if it wasn’t a big falling out, or you are still friends on social media, or occasionally even do a “happy birthday” here and there. Maybe things ended tumultuously, which doesn’t necessarily mean you can’t reach out, but it is something to think about.
Is it safe? Was the person you want to reach out to abusive or dangerous? Or even, are they not the most emotionally safe person? Or are they a pretty level-headed, nice person?
On a less intense level, do you believe they are the kind of person who can have a non-charged conversation? There’s a friend in my past that I will be meeting with to talk things out with who is very kind and loving. Even if nothing changes from it, I know that we would both be going into a conversation with respect and care. I have other ex-friends that I know are reactive, unkind, impatient, and genuinely are not open to seeing other people’s perspectives. I would not desire to engage in a vulnerable conversation with them.
When you were together (friends or a partner), what were their opinions on people reaching out/apologizing? I am someone who would probably almost always like to be apologized to, even if it’s been a long time. And it’s obvious that I am like this because when I am processing people of my past, I usually say things like, “I just wish I knew why…” or “I always wondered if they felt bad…” etc. Has the person you want to reach out to ever expressed sentiments like this, or the opposite of this? Similarly, I had a friend who expressed adamant anger and harshness towards people of her past (even though, in a lot of her rants, I usually agreed with the other person). I know that this person would probably not be the most receptive to me trying to connect.
Will it hurt their healing for you to reach out? I have an ex, who I actually do like. When I realized we lived in the same city, I wanted to connect. It had been eight years, I was married, and it was clear that we would not be compatible at all with each other romantically. We were also in high school when we dated. I happened to be friends with a friend of his, and they confided in me that this ex was perturbed that we lived in the same city. They felt uncomfortable being around me because of their own space in life. So, even though I would have loved to meet up and have coffee (and, again, show them that I’m not the same codependent teenage girl they once knew), I realized it would not be the best for them.
Is it for them, or for you? Do you think they would benefit from hearing your apology, and maybe even get some sort of clarity from it? Or is it just to ease your guilt? If you need their forgiveness in order to be content, then don’t reach out. But if it would help you rest easy knowing that you were vulnerable and tried to leave things on a peaceful note, perhaps reaching out is good.
What are your values, generally? And does this action align with your values?

Story pin image — photo from h 🐞 on pinterest

If you decide to reach out, here are some things to consider:

Consent can be tricky with this. I have been the sender of a DM or two that contains paragraphs of details, admissions, explanations, apologies, well wishes, etc. At the time, they felt heartfelt, sincere, and vulnerable. But looking back, I wonder if that was quite jarring to receive out of nowhere. They had no say if they were going to receive my novella of emotions. They were not prepared. I think this is what you meant when you said you didn’t want to trauma dump.
Consider asking for consent. Perhaps send a message like: “I have been thinking a lot about you and the regrets I have. I would like to apologize to you and offer some insight into the situation. Is this something you would be open to me doing? If not, I understand. Either way, I apologize for how things turned out.” Or something of the like. You could then go on to ask if they would prefer a text, an email, a call, or a meet-up.

You could also say something along the lines of, “I would like to apologize to you. I have written you a letter, and I’m wondering if you would be open to me mailing it to you.” Or, you can write an email with a clear subject line and a warning at the beginning for the contents, then text the person and say, “I owe you an apology. I have sent a lengthy email with my apology. There is no pressure to read it or reply.” That way they still have space around this information.
Prepare yourself for them being angry, cold, responding in a way that says their piece, or to not respond at all. Before you make a move, make sure you’ll be okay if any of these happen. If you still feel proud of your words, and feel like your actions are in integrity, even if they say something you don’t like/nothing at all, then that’s okay.

“I don't want to live life with regrets.”

I understand this. When my mom passed, my main motivator was not wanting to live with regrets and not living fully like her. And… it is impossible to avoid regrets in our lives. Every decision or action has an opportunity cost attached to it. Every decision has another decision we could make instead. While it’s good to remind ourselves that we only have this one life, so we need to live it authentically and boldly, we also should avoid a scarcity mindset. Life isn’t about avoiding regrets.

I'm scared of people overreacting wondering "Are you ok?" or "That's a little much" resulting in me being outcasted.

Well… it sounds like you are already moving! If you do have something to apologize for, likely that strain is being shown in the relationship already. If your friends push you away after apologizing, then perhaps that friendship wasn’t so solid in the first place. And, what do you have to lose?

Also. It sounds like you are trying to convince us to tell you that it’s okay to apologize and shoot your shot. So, it sounds like you already know what you want to do. You just want permission.