I recently “broke up” with one of my friends. If this has ever happened to you, you know it’s almost more awkward and stressful than when a romantic relationship ends. There are fewer rules, different expectations, it feels like uncharted territory. What constitutes a breakup between girlfriends?

It’s totally acceptable to end the friendship if a gal pal breaks an obvious rule, like stealing your man. But what if it’s more subtle than that? What if it’s something you can’t put your finger on, but you just keep walking away from each interaction feeling a sense of discomfort, or ickyness?

That’s what I was experiencing with my friend. It hadn’t always been that way. When we first found each other, she was an absolute Godsend to me. She was a person I’d trusted, laughed with, whom I’d shared Benedicts with at brunch, dog-sat for. She’d been my companion for countless happy hours, movie nights, Sunday dinners. She’d put me in Ubers, held my hair back when I puked, told me her secrets, brought me souvenirs from her vacations. I thought we’d always be tight.

So when our dynamic started to slowly shift, I didn’t want to accept it. Life was changing for both of us: I was in a serious relationship, working 9-5, and applying to grad school. She was going through a major breakup, working late nights in a downtown club, and acquiring a new group of party friends. There was no denying that our paths were diverting.

But what does that matter, I’d told myself. She was still the same person, a good friend. Someone I loved! It felt wrong to discard a friend based on circumstances. So I hung in there, determined to make the friendship work. The more I tried, the more I could feel the distance between us growing (sounds like a cheesy romance, I know.) It felt forced. I couldn’t shake the feeling that I was doing things I’d never otherwise be doing, just to accommodate the friendship.

What I came to realize is that circumstances do matter. And it’s not always about someone being a “good” or “bad” person. Often it comes down to commonalities, timing, where that person is and where you are in your respective lives. Is there anything to tie you together when your interests are so vastly different? If I’m waking up when she’s going to sleep every morning? If I’m cutting back on alcohol but she’s living off champagne and cocaine? I started to see that our common ground was quickly vanishing, that the things we connected on and shared were somehow slipping away.

People tend to think that if a friendship is toxic, that means that the friend is toxic. I’ve come to realize that’s not always the case. I think there’s a big gray area, and it can be very hard to determine if the friendship is worth staying in. When I thought about this scenario with my friend, I had a very hard time letting go because I was holding on to a lot of valuable memories. If you are in this boat, and you feel guilty letting go, but unhappy staying friends, consider these things:

  1. How do you feel before you see this person? This reveals a lot. I think we often spend time with people because we feel obligated, not because we actually want to. If you feel yourself getting worked up, stressing about what to talk about, how to dress, or who else will be there, that’s not a good sign. 

  1. Do you constantly accommodate her? How you spend your time with this person can say a lot about the nature of the friendship. Are you the one that does all the driving? Does she insist that you meet up with her friends, but never reciprocate and hang out with yours? If you love Mexican, and she loves Italian – what do you end up eating most times?

  1. How much do you share about yourself? Do you feel that this person honestly “gets” you, what your priorities are, and why you do the things you do? I was finding that every time I got an invitation to meet this particular person out, I’d make up excuses. When we would see each other, I’d shy away from sharing too much, deflecting conversation back to her. It reached a point where it just didn’t feel natural to talk about the things I truly cared about. I’d gotten one too many blank stares of disinterest.

  1. What is your friendship based on? Suppose you are drinking buddies with someone. If you have built your friendship over a series of Sunday Fundays, that should set off warning bells. Do you ever have movie nights or meet for breakfast? Go for a walk? Talk on the phone? Real friendships cannot be maintained by rubbing shoulders in the bottle service section. The same goes for friendships based on money, gossip, negativity…fill in the blank. Whatever the behavior, if it lacks substance, the friendship probably does too.

  1. How do you feel after spending time with this person? I would often feel tired, sad, or disappointed. Most of us lean on friends to feel supported, understood, and loved, so it can be a major letdown when we don’t get those things. I was finding myself wondering why I’m walking away from each playdate feeling so dissatisfied. I finally realized it was because that friendship no longer gave me anything positive.

If you ask yourself these five questions and someone’s name immediately comes to mind, it might be time to re-evaluate the friendship. We are all deserving of real relationships with genuine connections. We all want to be recognized and loved for who we are. It’s okay to shed the relationships that are no longer doing this for us.

By letting go of someone, you’re not being negative, you’re not judging or saying “no” to anything or anyone. You’re simply saying “yes” to yourself! Honor yourself and make space for the people in your life that do appreciate you.

As Mandy Hale writes in her book, The Single Woman, Life, Love and a Dash of Sass,Celebrate the people in your life who are there because they love you for no other reason than because you are you.”