Hi there,
Just about every day, someone asks me: How do you know when it’s time to end your relationship? Should I stay? Should I go?
The reason this question comes up so often is that it doesn’t have a neat, one-size-fits-all answer. Relationships are living, breathing organisms, shaped not only by two people but also by their histories, expectations, and wounds. And so the decision to leave — or to stay — will always carry weight. It will involve consequences on both sides. And when people reach the crossroads of a relationship, it takes courage to walk away. But it can also take courage to stay and do the work.
Here are the extremes: On one side are the people who want to leave at the first sign of trouble, convinced that conflict means they’ve chosen the wrong partner. On the other are those who stay long past the expiration date, sacrificing their well-being because they’re terrified of the unknown.
The real challenge is learning to tell the difference between normal relational growing pains and fundamental incompatibility or harm. That very distinction is what I want to explore today.
The Non-Negotiables
Let’s start with the clearest red line: violence. I’ve been asked many times, “They hit me once, but it hasn’t happened again. They’re in therapy. Should I give them another chance?”
The answer is no.
Abuse — whether physical or severe emotional manipulation — is not something to negotiate with. Research tells us that the likelihood of violence repeating is extremely high. If you’re rationalizing staying in the hope that this time is different, you’re gambling with your future safety.
And it’s not just about you. Children raised in violent or chronically disrespectful households pay an enormous emotional price, even if the violence isn’t directed at them. Leaving in those cases isn’t just an act of courage; it’s an act of survival.
That said, leaving isn’t always logistically simple. Sometimes it’s a privilege to have the financial or social resources to go. Many people stay in unhealthy situations because the alternative feels impossible. If that’s your reality, the first step is to gather support — friends, family, community resources — and begin to rebuild a foundation that allows you to make choices from strength rather than fear. But even when you do have the option, it can be paralyzing to imagine a completely different life. The what-ifs are endless. What if I can’t handle the loneliness? What if I regret it?
Yet when staying feels like a daily betrayal of yourself, when the cost of staying eclipses the fear of leaving, you already have your answer.
The Chemistry Trap
One of the hardest scenarios is leaving someone you feel intensely connected to but who consistently makes you anxious, insecure, or unsupported. You never quite know where you stand. They say they love you, but they disappear for days. They talk about the future but never follow through. Your nervous system is in a constant state of hypervigilance.
People often confuse intensity with intimacy. But real intimacy is steady. It calms your body instead of wrecking it. If your nights are sleepless and your days are consumed with trying to decode someone’s behavior, something is very wrong.
Chemistry might get you in the door, but character is what makes a relationship sustainable. If you can’t trust who someone is at their core, no amount of passion or history will make up for it. Do you respect your partner? Do they keep their word? Are they reliable and able to take accountability? Or do you constantly feel let down, deceived, or invisible?
And yet walking away from these connections is excruciating. Why? Because our brains are wired to crave the dopamine rush of unpredictability. It mimics love. It gives us hope that this time it will finally feel safe. But if your gut tells you otherwise, you need to listen. Staying becomes less about love and more about addiction.
Why I Broke Up with a Good Person
He was in many ways a catch. Intelligent. Attractive. He had a strong moral compass. He treated people with respect. He loved my dog. But there were things — some small, some enormous — that didn’t align with me or the life I wanted. Not then, not now.
The Hard Questions
For those in longer-term partnerships — marriages, co-parenting situations, deeply enmeshed lives — the calculus is different. You may not be facing abuse or chaos. Instead, you’re quietly asking yourself: Why am I unhappy?
Here’s where self-reflection becomes essential. Have you communicated your needs clearly and effectively, or do you expect your partner to read your mind? Have you been contributing to the relationship, watering it with the same effort you gave in the beginning, or have you pulled back? Have you sought counseling or learned new communication tools?
And finally, is your unhappiness because of your relationship, or because of your relationship with yourself?
None of this is about blaming yourself. It’s about knowing that if you don’t do this work now, you’ll likely repeat the same dynamic in your next relationship. Sometimes people discover that they’ve fallen out of love not because the love is gone, but because it’s been buried under years of unspoken resentments. Sometimes, people struggle to connect to each other because they feel disconnected from themselves.
But other times, the truth is simpler and harder: I just don’t love them anymore. Or, We’re fundamentally headed in different directions. And that’s when it’s time to acknowledge that not every relationship is meant to last forever.
That doesn’t make it a failure. It makes it a part of life.
How do you really know when you’re done?
You know when staying feels like a daily erosion of your spirit. You know when your gut tells you that remaining would mean betraying yourself. You know when you’d rather face the uncertainty of the unknown than the certainty of ongoing pain.
Sometimes the decision doesn’t come in a lightning bolt. It comes quietly, in the accumulation of small moments: rolling your eyes at each other, not caring whether you spend time together, realizing you don’t even like who you’ve become in the relationship. That’s when you recognize: It’s already over.
And here’s the paradox: Often, once you finally summon the courage to leave, you discover that the thing you were most afraid of — being alone, starting over — isn’t nearly as unbearable as you imagined. What is unbearable is living a life that feels misaligned with your deepest truth.
So, should you stay, or should you go? Only you can answer that. But whatever you decide, let it be rooted in honesty — with yourself and with your partner.
Love,
Jillian
When Your Life Is Not What You Thought It Would Be
Our blueprints tell us that they are the only paths to happiness. Without following our blueprint, we won’t ever find contentment or peace. But the reality is that most people’s lives do not end up exactly following the blueprint. And most of us have to sit with the knowledge that our lives did not turn out like they were supposed to