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Self-Sabotage in Relationships: Why Things Go Well Then You Pull Away

by ConfidenceConnect

You’ve been on plenty of dates. Maybe you’ve had short relationships. But when things start to get good, something shifts. You pick a fight. You focus on her flaws. You get distant or do something that pushes her away. Later you wonder why you did it. That’s self-sabotage in dating, and it’s often a way your brain tries to protect you from being hurt. Understanding that can help you change it.

What Self-Sabotage Looks Like

Self-sabotage in dating doesn’t always look dramatic. It can look like:

  • Finding something “wrong” with her as soon as it gets serious
  • Picking fights or creating distance when you feel too close
  • Cheating or flirting with others so you have an “out”
  • Not returning texts or being vague so she loses interest
  • Telling yourself you’re not ready, or she’s not the one, when part of you knows you’re scared

The common thread: you do something that reduces the chance of real connection, often right when connection is growing. It feels like you’re in control (you’re the one ending it or creating distance). But the cost is that you never get to see what could have happened if you’d stayed.

Why We Sabotage When Things Go Well

When a relationship starts to matter, the risk of loss goes up. If you’ve been hurt before, or you grew up in an environment where depending on someone felt unsafe, your brain may treat closeness as danger. Sabotage is a way to end the uncertainty: “I’ll leave before she leaves me,” or “I’ll give her a reason to go so I’m not the one who gets hurt.”

Another driver is belief about yourself. If deep down you think you’re not good enough for a good relationship, you may unconsciously create evidence: you do something that ruins it, then tell yourself “see, I knew it wouldn’t work.” That confirms the belief but also keeps you stuck.

How to Break the Pattern

Notice the moment.
Right when things are going well, do you feel a pull to create distance, pick a fight, or find a flaw? That’s the moment to pause. You don’t have to act on it. Noticing is the first step.

Separate fear from fact.
Ask: “Am I pulling away because something is actually wrong, or because I’m scared?” If it’s fear, name it. “I’m scared that if I get closer and she leaves, I’ll be wrecked.” Naming it doesn’t fix it, but it makes it easier to choose a different move.

Take one small step toward staying instead of leaving.
You don’t have to promise forever. You can decide to have one honest conversation, or to not send that text that would create distance, or to give it one more month and see. Small steps build evidence that staying doesn’t always end in disaster.

Check the story you tell about yourself.
If you often tell yourself you’re “not relationship material” or “bad at this,” write it down. Then write what contradicts it: times you showed up, times someone liked you, times you were kind or honest. The goal isn’t to pretend everything is great. It’s to balance the story so one bad outcome doesn’t define you.

How ConfidenceConnect Fits In

The same tools that help with approach anxiety and overthinking can help here. Writing down the thought (“If I get close, I’ll get hurt”) and checking it against the facts. Taking small steps instead of all-or-nothing. Building a habit of pausing when the urge to sabotage shows up. The app isn’t a replacement for therapy if this pattern is deep, but it can support awareness and practice.

When to Get Help

If you’ve repeatedly ended good relationships or you feel like you can’t stop yourself from sabotaging, therapy can help. There’s often past hurt or beliefs underneath the pattern. A therapist can help you work through that and practice new ways of relating. An app can support that work; it doesn’t replace it when the pattern is serious.


Related: Avoidant Attachment and Dating, Rebuild Confidence After a Breakup, Dating with Social Anxiety