Stuck Attracting the Wrong Type of Person? The Enneagram Can Help Break the Cycle

Have you ever had that moment after a breakup when you realize… Wait, didn’t I date this person before? Not literally, of course, but figuratively. Different face, different interests, but hauntingly similar emotional dynamics. 

Why We Repeat Relationship Patterns

Several psychological concepts explain why we tend to get caught in this Groundhog Day loop of love. The first is attachment theory. This theory says that, as adults, we tend to subconsciously gravitate toward emotional dynamics that felt familiar to us as children. So if caregiving was inconsistent or conditional in childhood, you might now find yourself drawn to relationships that feel... kind of the same. Not because you want the same suffering, but because your crush’s vibe matches your internal blueprint for what closeness with another human being should feel like.

John Bradshaw, the author of the book Homecoming: Reclaiming and Healing Your Inner Child, took this idea further, writing that we seek out these familiar emotional dynamics because our inner child is hoping to resolve unfinished business from the past. It’s as if your younger self is directing your dating life, hoping that this time the avoidant partner will finally choose you, or this time the emotionally distant one will finally show up. Spoiler alert: they usually don’t. But the subconscious keeps trying.

There’s also Arthur Aron’s self-expansion theory. This says that attraction may stem from a desire to grow into a fuller version of oneself, especially if the potential romantic partner possesses traits you feel you lack.

Whatever your reason for choosing the same “type” over and over, this doesn't mean that you are doomed to repeat this cycle forever. With the help of the Enneagram, you can see what's really driving it and finally break free.

Enneagram Reveals Your Childhood Wounding

The Enneagram doesn’t just “diagnose” your personality type. It can also help you understand why certain types of people keep showing up in your life and how to move beyond those patterns.

For example, having learnt that you’re a Type Two, you might realize that your urge to help and care for others is rooted in early experiences where your caretakers only validated you when you were being helpful or tended to their needs. So, you internalized early on that affection isn’t something you receive just for being you – it’s something you have to work for.  This can set up a pattern where, as an adult, you're drawn to distant or unavailable partners because that dynamic feels familiar. The hope is that being helpful will finally earn the affection you want.

For Fours, the pull towards emotionally unavailable partners has a different reason. The Four’s characteristic longing often starts with a childhood sense of feeling emotionally abandoned, even though your caregivers were physically present. This creates a pattern where connection always feels just out of reach, never fully arriving. New relationships echo that old longing.

Armed with these insights, you can begin to shift these patterns. For a Type Two, that might mean spending time with people who check in on you because of who you are, not what you do for them. For Fours, it could involve choosing partners who are emotionally available, even when part of you is still drawn to the intensity of longing that comes with unavailability.

That said, change doesn’t happen from insight alone. The Enneagram can help you connect the dots between your attraction patterns and childhood wounds, but true transformation happens when you actually start meeting those deeper needs in healthier ways.

Looking for Someone to Fill the Void

While some people keep dating the same type because of their childhood wounding, others end up doing so because they’re drawn to partners who embody something they feel they are missing, hoping the person could help them fill that void. But when you date from a place of lack, you often end up attracting people who are also dating from a place of lack, but in the opposite direction. And that can get heavy fast.

For example, you might have built your life around being strong and in control, yet secretly long for softness. You’re attracted to people who seem gentle and nurturing. But they may be looking for someone to protect them and take charge of issues they don’t want to face. At first, it might feel like the perfect match. But relationships built on mutual projection usually end in disappointment. No one can be another person’s emotional savior.

The Enneagram can’t eliminate projection, but it can help you set more realistic expectations. By understanding your own and your partner’s type, you’re less likely to assign an outsized meaning to a relationship and more able to see what each person can genuinely offer based on their personality traits.

Seeing Beyond Chemistry to Actual Compatibility

Sometimes, it’s not that you keep dating the same type of person, but that you keep ending up in the same type of emotional dynamic. The most classic scenario is where the relationship starts with intoxicating chemistry only to crash and burn when you realize you're actually deeply incompatible.

The Enneagram can help you break this pattern, too. When you understand your Enneagram type, it becomes easier to identify whether you’re able to connect on a deeper level.

For example, you might have dizzying chemistry with someone, but start to notice their hyper-independence and need for space. Maybe they say they “don’t believe in texting every day,” or they go MIA for a week after a really intimate hangout and then brush it off with a joke about “being a lone wolf." In the past, you might have doubled down, tried to prove your worth, and lost yourself in the process. 

But with the Enneagram insight, you might realize that kind of vibe is a long-term deal breaker because you’re a Type Two who thrives on feeling needed, not like you’re chasing after scraps of attention. Now, you can catch your type-specific red flags early and walk away before you get too emotionally entangled, saving yourself from getting stuck in an unfulfilling relationship. 

Keep in mind that the Enneagram can’t help you find your perfect partner or avoid all relationship mistakes. But it can help you understand your patterns more deeply, so you can make choices that actually serve you. The Groundhog dating loop might not vanish overnight, but you can start writing a new story—one that feels a lot less like déjà vu.