I was nervous and a little late making it to the diner that day. I thanked the universe that in our time apart, we had never once run into each other accidentally at a party or gallery opening. Had it occurred, our meetup may have never come.

When we met eyes, it wasn’t as stressful in real life as I had built up in the span of our years apart. The eyes I looked into were different. Mine were, too. And from there, two former best friends tried differently this time—unsure where to start, but content to walk the path together.

What happens when you need to let go of a friend? When is it ok to say, “This isn’t really working for me anymore”? Have you thought about friend breakups as much as I have in adulthood? To me—a person in a committed, monogamous relationship—this is as close as I’ve come to dating in a while, and it’s just as difficult to navigate.

Getting to know people as adults—with lives and bills and bedtimes—is frustrating, yet necessary. I never subscribed to the Midwestern take on friendship: kindergarten ’til death do us part. People fascinate me too much to only know a handful with the same exact experiences. But being too accepting and having many friends? Well, that perspective also comes with a price. I’ve had to walk away from friends for any number of reasons. We’ll get to that soon.

Friendships, be they short or long, are woven in and out of the fabric of our lives on this earth. Maybe you’ve had only a few; maybe you’ve had dozens at a time. Maybe you hold the word “friend” in high regard; maybe you meet a new one every day. When you think about how many friends you’ve had in your life, how many have stayed? How many are now just memories? Personally, I hate to regard anyone as just a “moment” in my life, but when you think about growth and the needs of a person, we as humans shed our needs constantly, and relationships are no different. When thinking about those moments in your life, remember that they brought you here. Don’t forget, good or bad, those friends brought you right here.

So…

When is it the right time to say see you later?

When you aren’t replenished by what you put into your friendship

After spending time with a friend, do you feel whole, loving, *energized*, and informed? Legit HAPPY? Well, great! You have a good friend who is filling your soul! Make sure you’re checking in on them as much as they do for you—they are gem humans with insight and empathy, and they deserve that same energy back from the people in their lives.

It’s a huge red flag, and time to set boundaries with that person—or, soon enough, leave the friendship altogether—when your friend doesn’t have the same capacity for you; when you feel depleted after spending time with them. Are you constantly talking about them and their issues without getting a word in edgewise? Do they call you only in the case of an “emergency” or as a reason to party? As a reformed party girl, this one hits hard. It’s like getting rid of f*ck buddies: Sure, they’re great at the moment, and you’ve got some great memories. But you’re looking for something that can happen during the day and over brunch now, not so much over booming speakers and three (or more) vodka sodas.

When milestones drift you apart

Whether it’s a committed relationship, having a baby, a change in job location, the fact that one of you is sobering up (let’s get HONEST), or a change in interests (see above), these are the things every adult struggles with when they have a longstanding friendship. For the sake of your new life—and let me just say GOOD 4 U—you *must* cut off the people who aren’t supporting you through those beautiful but difficult transitions. You owe it to yourself to be your favorite person if they aren’t equipped to be.

When you don’t feel the partnership is equal

If you don’t know where you stand with a friend, it’s time to leave. Walls are built up and it is not your job to break them down. I’ve felt used in friendships before, as if I was a pawn just to make others feel something about themselves. I can say with the greatest confidence that those are not, and have never been, your friends. No friendship should be transactional, conditional, or hollow.

I used to think losing touch with so many friends over the years meant I was shallow or unable to keep long-term relationships. While that could be true in some cases, I was being too hard on myself for learning to love and cherish the people in my life when I had them. I never wanted to let go—it just naturally happened. We grew up and grew apart. Like reminiscing on my childhood, I think of those relationships as wonderful, scary, painful, beautiful, profound, prophetic moments. I hope they meant as much to them as they did to me. I won’t forget them. I hold them dear. In my heart I thank them. Thank you for coming into my life when I didn’t know what I needed. Thank you for the good times and the hard lessons. Thank you for showing me what good (and not-so-good) friendships look like. Thank you for showing me what I need and what I don’t.

Decluttering your friend list can sound a little petty, but by considering all the gratitude you can give yourself and that person by walking away, you allow yourself to live authentically—without question, tension, worry, or resentment.

Just because you’ve invested time in a friendship doesn’t mean you must stay to see it through. Gone are the days we say that for romantic relationships; we shouldn’t say it for friendships, either.

The good news is that nothing is forever. When I met my friend in a little diner not far from home, I knew we’d meet in a different place than where we’d left off. Time hadn’t seemed like as much of a gift back then as it did now. If you have someone in your life who you want to let go so they can grow (and so you can, too), leaving them to do just that is a gift. It can lead you to a little diner—out from the cold, and into the warmth of a new friendship.

Vanessa McDuffie

Vanessa McDuffie is a writer, educator, and influencer living in Minneapolis. She lives her life like a cat; on the couch, near a window away from the elements. You can find her on IG.