Why am I so bad at dating? And how can I fix it?
So, strap in, buckle up, and let’s talk about the age old question: Why am I so bad at dating?
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Why am I so bad at dating? And how can I fix it?

I absolutely love when people tell me they’re bad at dating. I know it sounds crazy, but it’s actually the best possible thing you can say when your love life isn’t working out. Why?

Because when you ask “Why am I so bad at dating?”, you’re putting the ownership of the dating game on you.

You may not realize it, but that’s a HUGE step that most people never take. Instead, they complain about how everyone else doesn’t get it. Other people always “have the wrong eye color,” “laugh too loud,” “don’t pay the check when it’s time to foot the bill,” “don’t make enough money to be a serious partner”…

Blah, blah, blah. I’m already bored to tears over here. 

But I’m not bored of you, because you’re here to learn why your dates aren’t working out, and what YOU can do to fix it. 

So, strap in, buckle up, and let’s talk about the age old question: Why am I so bad at dating?

The best dating advice you’ll ever get: how to go from flunking dating to crushing it

Stop assuming negative things in others

If you’re here, you’re probably jaded from all the bad dates you’ve been on. Some of them may have been really, really bad. And because of that, you might assume that everyone on the market is terrible—that there’s no good men or women left out there for you.

Not true!

If you always assume other people are bad or unsatisfying, you’re in for a long and lonely life (sorry, not sorry). Just because someone doesn’t want kids right away, folds their laundry weird or doesn’t have the best relationship with their parents, it doesn’t mean they’re an awful partner who’s out to get you, ruin your life, steal your 401K and move to San Jose, etc., etc., etc. 

By assuming other people want what you do—a healthy, communicative relationship that’s full of compromise and mutual understanding—you’ll be in a much better place to date. 

Give people a shot. Go on that second date. You might be surprised at what happens.

Let go of “must have” relationship milestones and focus on what makes you happy

Tangential to my previous point, it’s important to let go of all those superficial “must have” milestones. If you don’t know what these are, they look like this:

  • If he or she doesn’t officially make me their partner after a month, it’s over.
  • We CANNOT become long-term partners if we had sex on the first date. 
  • I always saw myself with someone who has brown eyes, so this can’t be it. 
  • If I don’t feel a spark from the second we speak, it’s not worth pursuing. 
  • We should be moving in together after six months of dating seriously. 

These are rigid milestones that don’t allow for much breathing room. So, instead of thinking about milestones, think about the bigger questions:

  • Do they make me happy?
  • Am I my natural self around them?
  • Are they funny, genuine, and kind?
  • Can I rely on them when I need it?
  • Can I trust them?
  • Are they stable enough to enter a relationship?
  • Do we have the same bigger life goals?

Don’t commit any “first date killers”

Alright, this one’s easy. There’s a few things you should absolutely NOT do on a first date. Rapid fire, they are:

  • Talking about your ex
  • Telling them how many kids you want 
  • Talking about marriage
  • Refusing to pay for some or all of the bill
  • Complaining about the service of the restaurant or bar you’re at
  • Making fun of your date’s appearance, traits or qualities 

Yeah, maybe you like a relationship with a little bit of verbal sparring in it—but it’s not going to go well if you tell your date they’re wearing last year’s color the moment you meet them. Remember that relationships are built on trust, and when you first meet someone, neither of you knows enough about the other person to trust each other. 

Once you’ve built up enough rapport, you can talk about things like exes, marriage, kids, their gaudy shoe collection, the works. But just HOLD YOUR HORSES until you get a little further down the road, capiche? 

Do some groundwork in a journal

Are you sabotaging dates because you’re not over your ex? Are you not really interested in a long term relationship but you keep ending up in monthslong flings regardless? Are you unsure of what qualities you like in others?

These are all fair questions, and if you haven’t really done your homework and dug deep for the answers, it’s going to murder your dating game. 

Instead of self-sabotaging, pick up a journal and answer some of those important questions for yourself. Journaling can help you process feelings that you’ll need to work through in order to be a better dater, partner and romantic companion. 

Some journaling prompts you can start with include:

  • Write out a list of all your non-negotiables in a potential partner
  • Talk about what your ideal first date will look, feel and sound like
  • Ask yourself if you’re actually ready to date, or if dating is a distraction from something else happening in your life right now
  • Name three ways you could have more fun—and be more fun—on a first date

Talk to someone about what’s going wrong

It’s so hard to see what we’re doing wrong when it comes to dating. That’s because we’re too close to our own life to understand it from the outside. 

It’s sort of like how all your friends could tell your ex wasn’t right for you, but you couldn’t see it because you two were like, sooooo in loooooove. 

There’s an easy fix to this: talk to someone! Talk to a friend, your parents, your siblings, a coach, a therapist, anyone you want. Just make sure they’re someone you can trust who gives good relationship advices and wants what’s best for you. 

Who knows? You might be surprised at what they tell you about your choice in partners, your dating style, and what you want going forward.

Got more dating questions? We’ve got you covered. Talk to one of our coaches today about why your dating life hasn’t been panning out lately, or listen to our podcast about life, love and all its messy moments.   

Important note:
We are a coaching company with expertise in lots of different areas like mental wellness, career, relationships, parenting and a whole lot more. While coaching in The Journal That Talks Back™ can help you to take a deeper look at the above topics, we recognize that there are times when other resources, like therapy and/or counselling, may make more sense. As such, we have begun to develop a Mental Health Directory with well over 800 resources and we are investing time and effort into really growing it. It is also developed in a super user friendly way (we hope) so that it's easier to navigate than say another government website. Click the button below to check out our Mental Health Directory.
The Mental Health Directory