#436 - 5 Self-Sabotaging Dating Behaviors You Don’t Know You’re Doing
You might be sabotaging your own love life and not even know it.
Not because you’re broken, but because you’re human.
After coaching hundreds of midlife singles, I’ve seen how even smart, self-aware people unconsciously block the very relationships they want. Here are five subtle self-sabotaging behaviors and what to do instead.
- The “Endless Options” Trap
Let’s be honest, you’ve probably said this:
“I’ll just swipe a few more times. The right one’s out there somewhere.”
The problem? Too many options create choice overload...your brain starts shopping instead of choosing. You chase perfection instead of connection.
Fix:
- Pick one app. Keep no more than ten active chats.
- When someone matches your Must-Have list, move to a call within 72 hours.
- Follow the two-date rule: if values align and it feels safe, give them a second chance before deciding.
Curiosity beats comparison...every time.
- Letting Rejection Sensitivity Run the Show
After divorce, widowhood, or a string of failed dates, your brain becomes a threat detector. You interpret silence as rejection and pull away before you can get hurt.
That’s called rejection sensitivity, and research shows it predicts more conflict and fewer healthy relationships. You’re protecting yourself right out of love.
Fix:
- Assume positive intent until you see a pattern, not a single lapse.
- Replace tests with requests: “I like staying in touch during the day, does that work for you?”
- Practice “micro-bravery” once a week. Send the first message. Ask for the date. Express a real preference.
Confidence isn’t avoiding rejection, it’s trusting you’ll be okay when it happens.
- Attachment “Leakage”
You never tell someone your attachment style, but people feel it instantly.
If you lean anxious, you might overshare or “future-trip,” saying things like, “I can really see us traveling together,” after two dates. Your brain is trying to create security before you’ve built trust.
If you lean avoidant, you go the other way, interviewing instead of connecting. You ask logical, checklist questions because it feels safer than being emotionally open.
Both extremes kill chemistry before it can grow.
Fix:
- If you skew anxious: slow the emotional pacing. Be curious about their world instead of imagining your shared future.
- If you skew avoidant: share one personal story per date. That builds trust without forcing vulnerability.
- Follow the 30/70 rule — talk 30–40% of the time, listen 60–70%.
As Vanessa Van Edwards says, it’s about balancing warmth (making people feel safe) and competence (earning respect). Blend the two and you become magnetic...calm, confident, and deeply attractive.
- Negativity & Confirmation Bias
If you expect red flags, you’ll find them, even when they’re not there.
Midlife singles are experts at this because we’ve all been burned before. But “interviewing for disqualification” keeps you from noticing what’s right in front of you.
Fix:
- Apply the 5-to-1 rule: for every red flag you think you spot, name five positives. Maybe they were kind to the server or made you laugh.
- Separate discomfort from danger. New isn’t unsafe — just unfamiliar.
- Change your language: instead of “You always…,” try “I noticed X. Here’s what works better for me...Y.”
That’s direct, kind, and confident; the trifecta of emotional intelligence.
- Digital Disrespect
Let’s call it what it is; ghosting, breadcrumbing, or low-effort texting.
These may be common, but they’re toxic to your confidence.
Every time you tolerate low effort, you teach your brain to accept emotional scraps.
Fix:
- Close the loop: If you’re not interested, send one line: “Thanks for the coffee — no match for me. Wishing you the best.”
- Upgrade communication: After 6–8 messages, move to a call. Texting is for logistics; voice is for connection.
- Do an effort audit: If you’re carrying 80% of the planning, pause. Ask, “Would you like to plan something for next week?” If they don’t engage, move on.
Boundaries aren’t barriers, they’re filters for respect.
Your 30-Day Reset
If you want to change your dating experience, start small:
- Write your Must-Haves and Deal Breakers: behavior-based, not “vibe-based.”
- Use one app. Ten chats max. Call within 3 days.
- Follow the 30/70 share rule. Give two genuine compliments per date.
- Each week: send one brave message, set one clear boundary, and express one gratitude.
- End each week asking, Did I show up as the kind of partner I want to attract?
Small, consistent steps change everything.
Thought Reversals
“I’m just picky.” → Maybe. Or maybe you’re overloaded.
“I don’t want to waste time.” → Playing games wastes more time than clarity.
“If it’s right, I’ll just know.” → Chemistry is instant. Compatibility takes time.
Final Word
You’ve lived enough life to know love isn’t magic, it’s choice and courage.
If you’ve been unknowingly sabotaging your own results, that’s okay. Awareness is the first breakthrough.
If you’re ready to stop guessing and start dating intentionally, book a free 30-minute Discovery Call with me. We’ll review your Must-Have list and uncover what’s been holding you back.
And if you’d like a deeper dive into these five behaviors, including real client stories and practical fixes — watch the full YouTube version here.
You’ve got more to offer than you realize.
Let’s make smarter dating decisions so you can finally find your love for a lifetime.