I was having coffee with an old colleague last week when he mentioned running into someone we both knew from years back. “Should I reconnect?” he asked. The question hung there between us, and I found myself thinking about all the times I’ve watched people open doors they’d wisely closed years earlier.
After decades in negotiation rooms where people revealed their true motivations under pressure, I’ve learned that some relationships aren’t worth salvaging. Experts back this up with evidence about which personality types consistently damage our wellbeing. The difficult truth is that certain people will always take more than they give, no matter how much time has passed.
1. The gaslighter who rewrites your history
You know the type. Every disagreement becomes a debate about what actually happened. They insist you said things you never said, twist your words until you question your own memory, and leave you wondering if you’re losing your mind.
As Dr. Robin Stern explains, gaslighting is “an insidious and sometimes covert form of emotional abuse, repeated over time, where the abuser leads the target to question their judgments, reality, and, in extreme cases, their own sanity”. I’ve seen this play out in business partnerships where one party systematically undermined the other’s confidence until they couldn’t trust their own judgment.
The damage runs deep. Once someone has successfully made you doubt your perception of reality, that foundation crack never fully heals. They’ve shown you exactly who they are. Believe them.
2. The person who treated you with open contempt
I once watched a business partnership dissolve over eye rolls. Sounds trivial, but Dr. John Gottman’s research reveals that contempt is the number one predictor of divorce. It erodes relationships.
Contempt is different from anger or frustration. It’s the belief that you’re fundamentally inferior. When someone shows you contempt through their words, tone, or body language, they’re telling you they see you as beneath them. That’s not a misunderstanding or a rough patch. It’s a fundamental lack of respect that rarely changes.
Years later, they might apologize, claim they’ve grown, promise things are different. But contempt leaves a particular kind of scar. Your nervous system remembers even when your mind wants to forget.
3. The energy vampire who left you exhausted
We all know someone who leaves us feeling completely drained after every interaction. They monopolize conversations with their problems, dismiss your concerns, and somehow make everything about them. You hang up the phone or leave the coffee shop feeling like you’ve run a marathon.
I learned to recognize these patterns during negotiations. Some people approach every interaction as a taking opportunity. They’ve trained themselves to extract value without reciprocating, and that pattern becomes hardwired over time.
4. The boundary bulldozer who never heard “no”
Setting boundaries takes courage. Maintaining them against someone determined to break them down is exhausting.
I spent years learning to say no without explaining myself. It was uncomfortable at first, but necessary. The people who respected those boundaries stayed in my life. The ones who pushed, questioned, guilt-tripped, or ignored them? They revealed something important about how they viewed our relationship.
As Dr. Brené Brown puts it, “Daring to set boundaries is about having the courage to love ourselves, even when we risk disappointing others.”
When someone consistently violates your boundaries, they’re telling you they don’t believe your needs matter as much as their wants. That fundamental disrespect doesn’t age well. Time apart doesn’t teach them to value your autonomy. It just gives them new strategies to override it.
5. The friend who disappeared when you needed them
Dale Carnegie wisely observed, “don’t be afraid of enemies who attack you. Be afraid of the friends who flatter you”. But I’d add another category: be wary of friends who only remember you exist when they need something.
These relationships feel particularly hollow because they masquerade as friendship. They call during their divorces, job losses, and health scares. You listen, support, advise. But when you’re struggling? Radio silence. When you have good news to share? They’re too busy.
The pattern becomes clear over time. You’re not a friend to them. You’re a resource. A free therapist. An emotional support system they can activate on demand. Real relationships require reciprocity. Without it, you’re just performing unpaid emotional labor.
6. The perpetual critic who chipped away at your confidence
Some people can’t help themselves. Every accomplishment you share gets minimized. Every decision you make gets questioned.
I’ve watched talented professionals lose confidence because someone in their life consistently undermined their achievements. The criticism often comes wrapped in concern. “I’m just being honest.” “I’m trying to help.” But the result is always the same: you feel smaller after talking to them.
The damage accumulates slowly, which makes it dangerous. You don’t notice your confidence eroding until you catch yourself doubting decisions you would have made easily before. Recovery takes time, and letting that person back in restarts the erosion process.
7. The chaos creator who thrived on drama
Every interaction was a crisis. Every day brought new emergencies, conflicts, and theatrical performances. Being around them felt like living in a permanent state of high alert.
Researchers note that “people exposed to chronic stress age rapidly”. The chaos creators in our lives activate our stress response constantly. Your body can’t distinguish between a tiger attack and someone’s manufactured drama. The physiological response is identical.
I learned this the hard way in business. Some negotiators create chaos deliberately because they thrive in it while others flounder. But in personal relationships, this dynamic is toxic. You spend so much energy managing their crises that you have nothing left for your own life.
8. The promise breaker who taught you not to trust
Trust, once broken, leaves a specific kind of wound. The person who consistently made promises they didn’t keep, who assured you things would change but never followed through, who asked for one more chance repeatedly—they taught you something valuable. They taught you that their words mean nothing.
In negotiations, I learned that past behavior predicts future behavior with startling accuracy. Someone who broke promises before will break them again. The apologies might sound sincere. The reasons might seem valid. But the pattern remains consistent.
The cruelest part is how promise breakers make you question your own judgment. You wonder if you’re being too harsh, too unforgiving. But protecting yourself from predictable disappointment isn’t harsh. It’s wisdom.
Closing thoughts
Not every relationship deserves resurrection. Some doors close for excellent reasons, and reopening them invites the same problems back into your life with compound interest.
The hardest lesson I’ve learned is that you can’t negotiate someone out of what they’re committed to misunderstanding. People who hurt you before have shown you their capacity. Time might soften the edges of memory, but it rarely changes core patterns of behavior.
Here’s my rule of thumb: if thinking about reconnecting with someone makes your shoulders tense up, your body is remembering something your mind is trying to forget. Listen to it. The peace you’ve built in their absence is worth more than the false hope of their change.
