7 Ways You’re Making Your Dating Life Miserable (Without Knowing It)

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Remember that time we talked about all the ways you were totally sabotaging your dating life without even realizing it? Yeah, you guys LOVED that one. So, naturally, we’re back at it. Consider this your not-so-friendly guide on how to absolutely tank your chances at finding a meaningful connection. Buckle up, buttercup, because we’re about to dive deep into the wonderfully weird ways you might be making yourself miserable in the dating world.

Ever wonder how some people just seem to stumble from one frustrating date to another? Newsflash: it’s rarely accidental. While no one wants to mess things up, plenty of folks are masters of self-sabotage. Why? Because often, the real issues are hidden beneath the surface, the sneaky little things you don’t even realize are derailing your love life.

That’s where we come in. Every day, our inbox is flooded with people asking for help with their dating woes. And you know what we do? We don’t just address the obvious complaints. We dig for the secret stuff, the underlying patterns that, once fixed, make all the difference.

So, ready to learn how to date completely wrong? Let’s get started:

1. Using Your Partner as Your Personal Fix-It Upper: Feeling a bit lost, lonely, maybe even like a puzzle piece with a missing chunk? It’s tempting to think a partner will magically snap into place and make you feel whole. And sure, feeling loved and valued gives you a boost, but it’s a temporary high. You’re essentially slapping a band-aid on a deeper wound. Plus, guess who you’re likely to attract when you’re broadcasting “I’m broken”? Often, it’s the folks who thrive on that dynamic – the ones who like to hold the power, the narcissistic types. Real talk: become a whole, complete person with an amazing life first. Then, you can approach love from a place of wanting to share your amazing life, not needing someone to create it.

Editor’s note: Ready to attract love with a proven strategy? Watch this free video to learn the 7 powerful steps

2. Head in the Clouds: Dating the Idea of Him, Not the Actual Dude: You barely know him (and maybe you’re even actively avoiding learning too much). This leads to some serious FIB-ing – Filling In the Blanks. Cue the excessive wishful thinking and giving out “benefit of the doubt” cards like they’re going out of style. He’s waving red flags like a matador, but you’re hyper-focused on that one semi-decent thing he did (“OMG, he brought me a single daisy!”). He’s showing you exactly who he is, but you’re convinced you see some hidden potential that doesn’t exist. You’re basically trying to develop a photograph that was never taken.

3. The Endless Second Chance (and Third, Fourth…Hundredth): Okay, we’re all for a second chance. Life happens, people make mistakes. But beyond that? Hard pass. He flakes again? Done. You need boundaries, people! Respect yourself enough to know when enough is enough. Remember, it’s tough for people to fundamentally change. Implement a “one strike” policy for anyone you’ve been dating for less than 1-3 months, especially when major red flags pop up. Early on, they’re on their best behavior. Trust us, it usually goes downhill from there.

4. Playing it So Safe You’re Basically Invisible: Lack of clarity is the kryptonite of romance. You like a guy, but you’re only willing to show it after it’s crystal clear he’s head-over-heels for you. The problem? If you’re already riddled with self-doubt, what astronomical sign are you waiting for to be convinced he’s 100% in? Spoiler alert: you’ll probably never get there. You’re cushioning potential rejection by making him do all the heavy lifting. This creates a bizarre standoff, a downward spiral of disinterest where both of you lose. Put yourself in his shoes: “I’m dating this woman who seems…meh.” Why isn’t she interested? (Doesn’t like me? Has better options?). Would you invest more time and energy? Probably not. Take a chance, be a little vulnerable. The risk is worth the potential reward.

5. Swiping Your Way to Nowhere (and Other App Faux Pas):

  • The Serial Swiper: Treating dating apps like a video game, swiping mindlessly with zero intention.

  • The Picture Purist: Judging solely on heavily filtered photos (and being ridiculously picky about them).

  • The Perpetual Pen Pal: Letting chats linger for months on end. Are you secretly okay with never meeting? Procrastinating? Drop the “You’re one of the first guys I’ve chatted with this much without meeting. I’d love to meet you in person…” line. Or try, “You’re interesting over text, but I bet you’re even better in person.”

  • The Storyteller (of Fiction): Forming deep emotional connections with people you’ve never actually met, building elaborate narratives in your head that may or may not be based in reality.

6. Letting Him Date You on Easy Mode (aka The Doormat Syndrome): Oh, he loves this. He’s probably thrilled and might even send a thank-you note. But beware, it’s a trap! We tend to value what we work for (hello, cognitive dissonance). Making it ridiculously easy for him to be involved – planning everything, doing all the work while insisting you’re just “being nice” or “helping out” – is a recipe for disaster. Maybe you have a control issue, or you think his ideas aren’t good enough. Maybe you always drive, even if he offers to send a car or plane ticket. Maybe you don’t ask for much because you’re afraid of disappointment. Chasing guys and pouring enough emotional energy for both of you while excusing his lack of investment? Stop it. Just stop.

7. Fuzzy Goals = Fuzzy Outcomes (Surprise!): Not having a clear plan for what you want in a relationship is like setting sail without a compass. “Seeing where life takes you,” “taking it day by day,” “living in the moment” – these sound innocent, but they’re not long-term relationship mindsets. They set you up for short-term thinking, which inevitably attracts guys who are also thinking short-term. If you don’t stand for something, you’ll fall for anything. When you lack clarity, you can always find a few positive traits in anyone and use them to justify ignoring all the negatives. You might even try to base your feelings on his: “He likes me, so I can probably make this work and like him back.” Newsflash: that’s building a house on a foundation of “maybe.”

So, there you have it. Seven more wonderfully effective ways to make your dating life a special kind of hell. Recognize any of these patterns? Good. Awareness is the first step. Now, let’s ditch these self-sabotaging habits and start creating a dating life that actually brings you joy. You deserve it!

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