Three Mistakes That Keep Tanking Your Relationships

Get out of that wash-rinse-repeat cycle

Frank Vaughn
5 min readMay 24, 2023
Photo by JAIME CUADRA on Unsplash

Breaking up sucks. I’ve honestly never been through one that felt good — even the ones I was eager to initiate.

You spend time, money, and both mental and emotional energy on someone, only to eventually get to a place where you know it just isn’t going to work.

Which is a little like admitting failure, right? I mean, you’d think that at your age, and with your experience, you should be able to make just one relationship work. After all, what use is all that experience if you can’t?

Well…here are three reasons you keep failing.

Reason #1: You have no idea who the other person really is

Chris Rock once joked that when you date someone, you don’t actually date them — you date their representative.

Especially in the early days of a relationship, everyone mostly puts forth their best image. And that is rarely (if ever) an accurate picture of who they really are.

Remember when you didn’t have to open the car door yourself? Pull out your own chair at the restaurant? Pick up the tab when you were out together?

Remember the compliments and careful listening back when the conversations were brand new?

Then time passes, familiarity sets in, and the personality quirks begin seeping out from behind the best-behavior facade.

Once that initial picture gets even slightly distorted, many of us either turn and run for the hills or dig our heels in, set our jaws, and vow to muddle through to the other side.

Runners, listen up. Some people are definitely flee-worthy. Especially those who bring the sugary-sweet on the front end and then quickly reveal their nasty nature when they feel they have you locked up.

And don’t get me started on gas lighters, verbal and physical abusers, addicts, pimps, and hustlers.

Definitely run and do not walk to the nearest exit with those specimens.

Heel-diggers, it’s your turn. Why are you sticking around when you feel in your bones that this isn’t working? Why let yourself go through something that is only going to get worse?

What is your personal threshold for deciding something is definitely never going to be what you need before you do something about it?

“But, but…how do you know the problem is with them and not you?” you may ask.

Great question!

Reason #2: You have no idea who YOU really are

Do you find yourself bouncing aimlessly from relationship to relationship, kind of wet-thumb adjusting from one to another in the hope of fixing your luck?

Are you relying on luck to get this right?

I don’t want to get too far down the rabbit hole of whether people should use dating apps or not, but I will say that folks don’t usually turn to those on a winning streak.

Yeah, they can totally lead you to your forever someone — I’m sure we all know someone who won that lottery.

But before you turn to modern technology to send your vibe out to the world in the hope of hitting pay dirt, why not spend a little time examining that vibe?

What’s wrong with taking a few (days, weeks, months, maybe even years) off to really dig into what might be broken inside you?

If you keep swerving all over Relationship Road, slamming into the barricades on both sides and further damaging your soul, why not slow down for a minute?

Check in with yourself and figure out why you keep choosing the wrong people. Take some time to autopsy your previous relationships and see if you can’t diagnose the real, deep, inner issues that keep you from being happy.

Be honest with yourself. Really examine not just the results but also your motives moving forward. Are you dating again because you know you’re ready and able to love and be loved? Or are you dating again because you’re hurting and need healing, however artificial it may be?

Ask the hard questions of yourself so you can ask the important ones of someone else.

Which reminds me…

Reason #3: You’re asking the wrong question

Without much fanfare, I’m just going to throw some questions out here that a typical person might ask in the early days of a relationship.

  1. How attracted am I to this person?
  2. How attracted are they to me?
  3. How does this person make me feel?
  4. How do I make this one work?

Attraction is important, and I don’t want to hear differently. When deciding whether to attach to someone we evaluate looks, body language, verbal cues, emotional chemistry…

Before actually getting to know someone, the superficial things are really all you have to go on. If you stay in that place forever, then go ahead and bank on failure right from the start.

Feelings are important too but, as pointed out above, they can lie to us if we haven’t done the work of really putting a thing through its paces. If we aren’t attuned to the reality of the person across from us. If we lack the proper self-awareness.

Really, it’s that last question that will get you in the most trouble. How do I make this one work?

If you are asking that one, you might as well admit one of the following things:

“I am not attracted to this person, but I’m lonely and they are interested.”

“This person does not find me attractive, so I need to change my looks and personality so they will.”

“This person comes off like a douche bag now that I’ve gotten to know them, but who else is going to go out with me? I need to suck it up and accept them for who they are.”

“I’m acting like I always do in these situations and it’s putting yet another person off. I need to try harder to be something I’m not so they don’t leave.”

Fake It Until You Make It simply won’t get you anywhere in a relationship. Rather than try to pound yourself or the other person into an unnatural shape, ask a much more important question:

“Does this really work for me?”

It is such a heart-preserving and time-saving thing to be honest with yourself when you realize you are pushing a thing that should not be.

And if you’re doing a completely honest assessment of a potential long-term relationship and you realize it is almost working, then do the additional work of figuring out if reasonable compromise and minor adjustments might really make it shine.

If you find, though, that the only way this will work is if one or the other of you has to sell out your authenticity or invalidate the other’s feelings, then make the tough call and hit that eject button immediately.

Relationships are never easy. Not the good ones, and certainly not the bad ones. Don’t be afraid to do the work when one is truly worth it.

If you know it isn’t though, then stop wasting your time and hit the bricks.



Frank Vaughn

Regional Emmy- and AP-award winning journalist and writer. Everyone’s brother.