The Jupiter-Square-Chiron Transit Will Totally Transform Your Relationships

Have you ever liked someone just because they liked you first? It may seem relatively innocent, but it’s also a surefire way to attach self-worth to external validation. Which, what a coincidence, is exactly what this rare Jupiter-square-Chiron transit is all about! On October 23, these two celestial bodies are forming a 90-degree angle for the first time in six years to ensure your love is actually rooted in authenticity.

Sound intense? It is! And here’s what it means for you.

Remind me, what does Jupiter symbolize in astrology?

Jupiter governs hope, faith, opportunity, and the quest for higher purpose. Whenever the largest planet in our solar system is involved, we’re encouraged to dream bigger, reach further, and trust in possibilities — even ones that feel unknown or scary. It’s the teacher, the philosopher, and (sometimes) the gambler.

Since early June, Jupiter has been in Cancer, a cardinal water sign tied to safety, roots, and emotional truth. Jupiter actually loves being in this sign (it’s considered “exalted” here), which means Jupiter is truly thriving right now, encouraging us to expand our capacity to care, to nurture, and to belong. Of course, Cancer (the crab) can also cling on a little too tightly, and under this influence, Jupiter’s instinct to protect can morph into possessiveness; what starts as love can harden into control. So now through June 30, 2026, when Jupiter enters Leo, we’re learning how to expand courageously while also trusting the process. If we need to white-knuckle a situation into existing, that’s not love … that’s a problem.

And what about Chiron?

Interestingly, Chiron isn’t a planet; it’s a comet with a complex myth. In astrology, Chiron represents the “wounded healer,” a symbol of both our deepest pain and our greatest healing potential. Chiron shows where we feel perpetually raw, but also where our compassion and wisdom live — the parts of ourselves that can help others once we’ve faced our own scars.

Chiron entered fiery Aries in 2018 and, since then, it’s been exposing wounds around selfhood and autonomy. Aries asks, “Who am I when I’m not waiting for approval?” and “Do I have the right to exist as I am?” Chiron in Aries brings up insecurities about independence, assertion, and the fear of being forgotten or silenced. Its medicine, however, is radical self-acceptance: claiming your identity without apology.

Why are they “square”?

A “square” is an aspect in astrology; an “aspect” describes the relationship between two celestial bodies, determined by their geometric distance in the sky. Squares are 90-degree angles. —I like to say that a square is the shape an arm makes before elbowing you in the stomach. Yes, squares can be painful — but they teach us invaluable lessons and inspire us to take action. Like telling the person who is about to elbow you to back the hell off.

Squares demand integration, so when Jupiter in Cancer squares off with Chiron in Aries, we’re confronting a contradiction: the desire to nurture and the need to assert. Jupiter says, “I want to love and be loved fully,” while Chiron replies, “You don’t own me!” This aspect challenges us to examine how we love — and how we let ourselves be loved — without shrinking, performing, or rescuing.

This is just the first part of a three-chapter story, one that will continue unfolding over the next several months. Together, Jupiter and Chiron reveal where our growth has outpaced our healing, and where emotional security might be cushioning unhealed wounds. This energy can manifest as overextension — trying to fix everyone through caretaking — or as retreat by hiding behind old, defensive habits. But growth that ignores pain isn’t sustainable: To evolve, we must let vulnerability reshape what we believe in.

Wait, it’s part of a series? What does that mean?

Jupiter and Chiron will meet two more times, creating a three-act drama of growth and healing that unfolds over the next ten months. After this initial connection, they’ll meet again on December 21 (which just so happens to coincide exactly with the winter solstice), deepening the reckoning and inviting reflection as we step into a new season of contemplation.

And the final connection between Jupiter and Chiron will take place on July 1, 2026, just one day after Jupiter enters Leo. By that time, Chiron will have also progressed into Taurus (on June 19), kicking off a new six-year cycle focused on stability, embodiment, and self-worth. Meeting at 0 degree (each celestial body’s starting point on a new journey) will add a new dimension to this narrative, one centered on rebuilding confidence from the ground up. It’s not just about what we believe or how we assert ourselves; it’s about what we value, what we hold sacred, and how we root those lessons in reality. When these two meet again, the healing shifts from theoretical to tangible, allowing us to see all the work we’ve done on ourselves in real time.

So what does Jupiter-square-Chiron mean for me?

In short, your focus should be on healing your self-worth. If Jupiter in Cancer is revealing where you crave connection, then Chiron in Aries is exposing how a fear of rejection may actually be driving that need. Together, they ask you to build belonging from the inside out — not from approval, comfort, or caretaking, but from confidence. The square pushes you to love without fixing, to care without clinging, to pour in without draining out completely.

Under this sky, don’t be surprised if old habits resurface: people pleasing, perfectionism, or the urge to disappear when things get hard. Notice, though, that these patterns no longer fit the life you’re growing into. Jupiter-square-Chiron asks you to stay open to that evolution. By the time this series is over, your relationship to care, vulnerability, and courage will be completely rewritten. And you’ll be better off for it.