on reconnecting with people from your past

Photo by Kelly Sikkema

I think there’s this idea that connecting with the past means you’re regressing…

That you’re choosing to move backwards instead of forward. For that to be true, life would have to be 100% linear, and we all no that’s not the case.

In fact, I believe reconnecting with people from the past is one of the most emotionally mature and forward-thinking things one can do. It requires a level of bravery and self-awareness that many people lack.

All of those toxically positive clichés like “the best is yet to come” and “leave the past in the past, the present is a gift, that’s why it’s called the present” and my least favorite of all, “everything happens for a reason” are not only reductive; they’re dismissive and teetering on dehumanizing.

Yes, you will meet awesome people in the future. No, you’re not a fool for wanting to reconnect with awesome people you’ve already met.

I recently started reconnecting with some incredible humans.

I spent a few hours chatting with my former college roommate, a few old friends and my best friend from Uni. I’m so fortunate that they crossed my path then, and that I have the option to know them again, now.

One thing about me is I don’t like broken bridges. That doesn’t mean that I avoid closing doors, but I certainly try not to slam said door, drop-kick the handle and give them the finger as I walk away cackling.

Blame the Girl Scout in me, but I truly do try to leave every place (and person) better than I found them. This applies to strangers I pass on the street, my local green grocer, and well, people I spent 4 years living, working and studying with.

Platonic or romantic, some things just fizzle away. It doesn’t have to be this dramatic and painful end. Oftentimes, it’s more like an ellipsis that gets longer and longer.

This makes it easier than ever to reach back out. I’m also notoriously bad at holding grudges, and I can pick things back up whether it’s been 2 years, or 10.

But, there are a few ground rules that I always keep in mind.

How to Successfully and Safely Reconnect with People from your Past

Always ask them who they are now.

While it’s okay to reflect on past shenanigans, it’s not okay to hold on too tightly of an out-dated version of this person that no longer applies.

Hold space to get to know them as they are now, and try detach yourself from this fossilized image or idea of them you once held.

Everyone deserves the freedom and space to evolve without guilt, shame, or being constantly reminded of who they once were. No one wants to be in a cage, even if it’s a golden one.

You’ll be grateful when they show you the same grace.

Imagine if you were still being seen through the lens that saw you at 19 or 21, and just how limiting that would feel.

This is not the time to shame folks for how much, or how little, they’ve changed, how different they look, or don’t look, or hold them to passing promises uttered many moons before.

Meet them where they are.


Try to make new core memories

The line between appreciating the past, and living in the past can get blurry.

Society looks down upon the 35-year-old man wearing his college football jacket, the almost-40-year-old trying to fit her now-too-juicy bum into those Juicy track pants, and we feel deep sympathy for the quinquagenarian veteran sharing war tales long gone.

Memories are fallible. Memories are subjective. Memories change.

They require upkeep.

You have to be committed to making new core memories because that story about how you drunkenly stripped down to your underwear and streaked across campus to a 1-ton boulder will lose its charm faster than you can say “Are we really doing this?”


“I may or may not be allergic to small talk. ”

Ask the right questions

“How’ve you been?” is a bit silly when you’re asking someone to fill in the gaps for the past 10 years.

Let people tell you what they want to tell you at their own pace. A decade is a huge amount of time to fit into the question, “How are things?”

I’m extremely earnest, and obviously okay with sharing , as I write about my innermost thoughts on the internet, so I ask questions and I answer them too.

”What do you love most about your life right now? What would you change?”
”What parts of you are still the same, and what has changed since we last knew each other?”
”What’s your preferred communication style and frequency?”
”What do you want me to know about you?”
Or even, “Surprise me!”

I do my very best to avoid saying things like “you always used to” or “did you ever do X, like you said you would?” or “I know you” cause, really, I knew you, but I’m getting to know you now.


SO!


I may or may not be allergic to small talk. I admit that my approach to conversations can be a lot for some. I’m insanely interested in understanding, knowing and appreciating what makes people human.

Unfortunately, “so, what’s up?” doesn’t even scratch the surface.


Set boundaries

The more I think about things, the more I’m convinced that yeah, your girl is probably neurodivergent… which is not a bad thing at all! I just have to understand that not everyone thinks about a situation the way I do.

I will straight up ask someone: what kind of texter are you? Are you okay receiving voice messages? Are you uncomfortable with long written messages? What’s your timezone?

I ask these types of questions because I want to know the answer, and if I can avoid clumsily crossing a line, even better, right?

Ask. Be proactive about avoiding unnecessary communication fumbles. Understand people’s boundaries out of respect. Hopefully, it works both ways.

Also, the world is a dumpster fire, most people are holding on by the tiniest of threads, so it’s the least we can do…


Adjust people’s expectations.

I don’t do drive-by, insincere friendship bids. If you’re going to open up the dusty broom closet of the past (spiders, the original iPhone from 2007, Sketchers, and all) just to say “hey, girl, hey” and never talk to them again… don’t. lol Keep that closet door closed.


Apologize if you need to, and always just in case

This is probably the most important thing: apologize.
Even if you can’t fully remember, and yes, even if your intentions were pure. You literally never know what people have held on to over the years, and how heavy it’s been for them.

Your drunken snub at a frat party might’ve really hurt them.

I also do this because, well, I’m not that girl anymore, and I believe it’s fair to take accountability and provide any type of closure I can for the person I’m reconnecting with.

Otherwise, it’s messy. You rock up a decade later, stirring up feelings, emotions and you look like this while you do it:

Imagine that shit!?


Lastly, understand that not all relationships are meant to last a lifetime. Some truly were linked to location, convenience, or a moment in time.


If after getting to know this person as they are now, you realize that you don’t have as much in common as you thought, or worse, that you don’t like this version of them.

Don’t panic.


This is an inherent risk. It doesn’t denote failure or wasted time. It’s a blessing and a lesson. A blesson? lol (It also still hurts like a bitch, depending on who the person is…)

I’ve seen both ends of the spectrum and everything in-between.

If you take nothing from this piece, please remember this: meet people where they are, and hold space for both of you to show up as you are in this moment, not who you were then, who you said you’d become, or the idea you had of yourself or the other person.

After you do that, just let things flow and see what happens! At least, that’s what I’m trying to do. I’ll tell tell you how it goes (obvs).

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