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October 2, 2014 11:25 AM EDT

This story originally appeared on xoJane.com.

“Friends forever” is sweet to write in a yearbook, but sometimes we outgrow old friendships — and that’s okay. Devastating, but okay. It can feel like the very antithesis of friendliness both to recognize when a relationship no longer serves us, and moreover, to retire it.

Think of a friendship like a piece of cake. (Not that friendship is easy, but — just imagine some cake.) You can let it sit out and forget about it; it’ll get stale. You can stick it in the fridge; it’ll be fine for a while, but at a certain point you’ll smell it and you’ll know it’s gone bad. You can shove it in the freezer and preserve it; but not indefinitely — the quality will degrade over time.

The best option, the one that requires the most amount of care: set that piece of cake under a magic glass cloche. This cloche will protect the integrity of your friendship over vast periods, so long as you maintain it.

Thing is, you only get so many magic cloches. You can’t use them on every friend, nor should you. Not every friendship is meant to last your lifetime. And when a friendship expires, the answer, more often than not, is: chuck it. Eating expired food will make you sick. Struggling to maintain expired friendships will make you sicker.

What are the warning signs that a friendship is past its prime?

You and your friend no longer share the same interests or values. Your friend injured you in some way. You frequently feel harassed by your friend to be a better friend.

All of the above are indications that the friendship may have merely lost its luster, or, more alarmingly, turned toxic, and the course of action varies depending on the issue at hand. The common denominator remains: minimizing pain for all parties concerned is key. Good friends remain just that — good, kind, considerate friends — even when a friend breakup is at hand.

The Friend Who…Who?

This is a formerly close friend who really isn’t high on your radar right now, but for some reason, one or both of you feels obligated to continue going through the friendship-upkeep motions. Maybe you two travel in different circles these days, or perhaps you’re separated by great distance. This could be a friend who puts painstaking effort into meeting up, even though you two aren’t really in each other’s lives anymore. Or this could be someone who, when you run into each other on the street, the stilted catch-up convo always ends in, “We should get lunch!”

Could the friendship be worth reviving?

Hey, maybe you really miss this person. Assuming that she is equally into the idea of reconnecting, pull out your day-planners and go for it.

If not…

This person sounds like an acquaintance. And acquaintances are terrific! Acquaintances are a delight! It’s nice to know a bunch of different cool and interesting people! But you don’t necessarily need to designate time towards boosting a relationship that’s not actually there. If you’re the one who typically caves with the frantic “Lunch?!” suggestion common to random run-ins, be strong. Don’t do it. Who says you need to pretend you want lunch? It’ll feel awkward to not extend yourself, but if the other person isn’t pushing you into Let’s Schedule This territory, end the conversation with a pleasant, “So great to see you!” AND SCENE.

What if the friend won’t let go?

Okay, so you’re just not that into Friend, but Friend’s rooted down and ain’t going nowhere without a fight. She may not realize that you’re not feeling it. If she isn’t doing anything particularly wrong, ask yourself: is there any real harm in sucking it up and committing to the occasional get-together? This person may need you in her life more than you need her, and the only thing you’d be losing is a couple hours, plus whatever personal pep talk it takes to stick a smile on your face.

The Friend Who Hurts You

This does not mean physical harm. (Run away. Run to the police.) Rather, this is a friend who causes you emotional anguish. This friend has betrayed you, backstabbed you, badmouthed you, lied to you, or belittled you. Those violations constitute manipulative behavior, and are unacceptable.

There’s also a subtler purveyor of manipulation: the narcissistic user. This is a person who is so consumed with himself and the litany of his own personal problems and aggravations that the entirety of your time together is spent on him. He can’t see beyond his own ego to connect with you as an individual, and uses you to feel better about himself. You often make excuses for him along the lines of, “Oh, it’s cool. I just know I can’t talk to him about my stuff.” What you may not realize is that this friend is inflicting real pain on you by erasing your needs from the equation. You’re his gratis psychologist; you’ve been scammed.

Could the friendship be worth repairing?

Let’s focus on that narcissistic user friend. (As for all the other, more abrasive harm-doers? Ditch ‘em and run-don’t-walk to your closest MeetUp Group activity.) Say you confront him on his past transgressions, and he apologizes. But will he change? Do people actually change? The jury’s in, and the votes are split. Optimistic humanists believe that people can better themselves if they try, while those nihilistic suckers who’ve been beaten down one time too many reckon you can’t teach an old friend new manners.

Here’s the long and short of it: YOU can’t change your friend. You can’t change your partner, you can’t change your co-workers, and you can’t change your parents. Your friend, like everyone else, needs to make the proactive decision to change himself.

For those positivity nutcases out there (and I count myself among them), practice caution and allow the jumpstarted relationship one more go on a trial basis.

If not…

The first time you feel taken advantage of or used in any way, pull the plug. You need to protect yourself, and you are worthy of friends who treat you as an equal, not as their servant/therapist/parent/maid.

What if the friend won’t let go?

Being blunt in this situation may feel very scary, and the last thing you need right now is a confrontation that devolves into your now ex-friend berating you. If you feel like you need closure with this person, be honest as you say goodbye. But also be prepared for the backlash. It’s almost impossible to walk away from conflict with a narcissist unscathed.

The safer tactic? Particularly if this person is quick to attack you? Cut off communication, and surround yourself with friends who legitimately support you. This is the recommendation for those struggling to leave verbally abusive romantic relationships; why not adopt the same strategy with friends? It’s not cowardice; it’s pragmatic self-defense.

The Friend Who Guilts You

First, let’s make one thing clear: The Friend Who Guilts You is NOT the counterpoint to The Friend Who Hurts You. There is no cause-effect here, as these are two different scenarios. This is a friend who guilt-trips you endlessly, and, over time, you’ve realized you’re actually not guilty.

This is the friend who tells you constantly that you are a terrible friend. “You never call me.” “You care about your other friends more than me.” “You’re abandoning me.” She’s high maintenance, and you suck at maintaining her.

Her mopey whining is another version of narcissism, sure, but many of us are less likely to nose this type of manipulation out — particularly those who prioritize caretaking above all and jump to self-improve when accused of falling short.

Here’s how this typically plays out:
Your friend confronts you.
You’re confused.
Your friend accuses you of various transgressions.
You’re still confused, but feel AWFUL.
You apologize.
Your friend forgives you.
You make sure to be extra attentive to your friend. How could she possibly feel bad/sad/mad now!
Time passes.
Your friend confronts you again.
Rinse, wash, repeat.

Could the friendship be worth refocusing?

If this is a friendship that means a great deal to you, and you feel like you’re being the best-friend-you-can-be-dammit, tell your friend how you feel. She may not be aware that her actions or words are so reproachful and causing you such grief, or she may have her own reasons for behaving this way that she needs to air out.

In either case, it’s best to be upfront. “I don’t feel great about myself when we hang out together,” is a good way to start, and you’re right if you noticed that this strategy begins by placing the brunt of responsibility only half-accurately on you. However, when you elaborate, it will be clear that there’s something off-kilter in this dynamic that reflects equally on you both. Coming from an angle of, “Help me help you,” as opposed to “Sweetheart, you’re batty,” invites a minimally combative interaction.

If not…

This friendship may just be too exhausting, with two few checkmarks in the pro column and several pages worth of notations in the con, to prolong. In that case, I don’t blame you for hightailing it out of there. You should still attempt to be honest about why you’re backing out of this friendship; but she may not be a person who’s able to receive constructive criticism. Do not feel badly if your friend breakup is, shall we say, an ordeal.

What if the friend won’t let go?

She may cry. She may beg. She may remind you of the good times you shared. But the fact remains: if your time together is not productive and beneficial to you both, leave. There are so many other life-sucking aspects to your day-to-day — job-related stresses, difficult family members, financial anxieties — and you need to ration your emotional resources. A friend who spins drama like your Great Uncle Larry spins torturous yarns is not worth the headache.

Ending a friendship is no fun.

Period. For any of these individuals to have stayed in your life this long means you care a great deal about them. You’ve probably had some super fun/wacky/memorable/life-affirming/insert-applicable-adjective-here times together. Let’s not discredit the good when cataloguing the bad.

But if you’re expending energy on a relationship that just isn’t fulfilling, consider exactly what you’re losing by putting the friendship aside, and compare it to what you’re losing by muscling to keep it afloat.

Protect yourself. Seek out friends who support you and validate you, and I don’t need to tell you that it goes both ways, because, let’s face it: Anyone would be lucky to call you a friend.

Stephie Grob Plante is a writer and former worker bee in the ever-buzzing NY film/TV production hive.

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