Are You Dating The Same Guy Over And Over Again? Maybe.

Are You Dating The Same Guy Over And Over Again? Maybe.

I'm pretty sure that, at this point, it's pretty safe to say we've all heard that the definition of insanity is doing the same things while expecting a different result. But I can't help but wonder how many of us apply this to our dating situations.

Take this one woman I know. Around every six months or so, she hits me up on email to tell me that she's met the perfect guy for her. I've been receiving these kinds of messages for at least a decade now, so the dialogue is usually the same.

Me: "How long have you known him?"

Her: "A few weeks."

Me: "What's so awesome about him?"

Her: "We just have a connection. It's hard to explain but I think this is it."

Me: "You already know what I'm gonna ask you right? Have you slept with him yet?"

Her: "Yeah. But this time is different."

Me: *crickets*


Fast forward to a few months later…

Her: "Well, it looks like things aren't gonna work out after all."

Me: "What happened?"

Her: "He says that I'm too intense and that he's not ready for anything serious."


Usually, she'll end her email with something along the lines of men are jerks and she wonders if she'll ever find true love. She's not exceptional in this case. I know a lot of women who feel the same way. But as someone who is not new to this kind of rodeo ride, there is a big part of me that wonders if some of us are jumping to generalized conclusions about men simply because we're not willing to look within.


What I mean by that is, I wonder if the real issue isn't that we can't find good guys, but it's more like we keep dating the same person over and over again. Sure, each man may look different but at the end of the day, could it be that we're caught up in a cyclic form of an emotional hamster wheel without even recognizing it?

If there's a part you wonders if you're lumping all men together because you keep dating the same kinds of guys, here are some telling signs to look out for.

6 Signs You Keep Dating The Same Guy Over And Over Again

1.You Always Seem to Break-Up With Guys For The Same Reason(s)


Break-ups hurt. Remembering them do too. I totally get that. But if you want to get to the root of whether or not you keep dating the same guy (or type of guy), purposeful reminiscing can actually do you some long-term good.

Take out a sheet of paper and think back to your last five relationships (or situationships). Now try and be as unbiased as possible as you write down the reasons why things came to an end. Were they scared to commit? Did you find yourself doing most of the work? Was there a lot of sexual chemistry, yet not enough of an emotional connection?

When I think back to a constant in a lot of my relationships, if there's one thing that was a common thread for me, it's feeling like I was being taken for granted. Yet when I stepped back and thought about how I got there, each and every time, I had to accept that I was willing to do a lot without requiring certain things in return.

It wasn't until I relived the break-ups that I realized that I kept attracting the same kind of guy because I never processed the common thread that connected them all.

2.You Never Make Time For Self-Evaluations


One of the toughest parts about being in marriage life coaching sessions is when one person thinks that their marriage would be fine if only their spouse made some changes. Not only is that pretty arrogant, but it's pretty self-delusional too.

None of us like to hear this, but if there's one thing that all of our exes have in common with us is us. That said, what were some of the words that the men in your life used to describe you? Needy? Controlling? Impatient? Insecure? Emotionally unstable? Suffocating? Petty? Relationships are mirrors. Sometimes they show us some of the very things we don't want to see about ourselves.

I'll give you an example. Let's say that you seem to always attract narcissists or sociopaths. Something that those kinds of men look for in a woman is insecurity, the fear of confronting matters, and the propensity for excessive people-pleasing. If you're wondering why you're always feeling manipulated or drained in your relationships, have you ever thought about if you have some of those traits?

If you're trying to figure out why you keep dating the same kind of individual, first, identify what kind of men you've been dealing with. Then look at what weaknesses they are drawn to (Psychology Today is one site that provides a wealth of wisdom on topics like these). If you have some of those qualities, remember — you can't change other people, but you can always improve upon yourself.

Sometimes just a little bit of self-evaluating and adjusting can be all that you need to break certain dating patterns and cycles.

3.You’re A Poor “Relationship Editor”


Whew, times flies! I can't believe that it's been over 20 years now since Juanita Bynum laid us all out with her sermon "No More Sheets". Out of all of the hot points that she hit, the one that has always stayed with me is the fact that we'll oftentimes miss someone from our past simply because we only replay the good times (including the good sex) in our heads. It's like we're wired to subconsciously edit out the heartaches, disappointments, and betrayals.

This is just one more reason why we can find ourselves dating the same kind of dude. If you're always finding yourself with a seductive cheater but every time you think back to your exes, you only remember how charming and romantic they were…see how that can result in you constantly being with someone who has the same attributes and the same character flaws?

If you don't want to date the same guy, be intentional about not editing out the bad stuff from each of the past ones. It's the bad stuff that teaches the real and lasting lessons so that we can grow.

4.You’re (Far Too) Comfortable With Routines And Patterns


Sadly, some of us would rather stay in something that is, at best counterproductive and, at worst toxic simply because it's familiar to us. Sure, you might not like being involved with guys who are not attentive or aren't as proactive as you might like but at least you know how to deal with those kinds of dudes. Right?

I'll raise my hand in this class and say that I used to have a real knack for getting involved with my male friends. To me, I thought it was "safe" because at least I knew they cared about me. But a guy caring about you vs. loving you so much that he doesn't want to be without you are two totally different things.

For a long time, I wasn't in love with myself, so I attracted men who felt the same way. They cared about me about as much as I did (some of y'all will catch that later).

The gal I referenced at the beginning of this piece? Her pattern is smothering guys too soon and confusing great sex for a solid connection. Intellectually, she knows that she deserves more. But she's settled for so long that she'd rather stick with what she knows than be alone.

It might sound cray-cray, but it's an epidemic, the number of women who do the exact same thing as her and me.

5.You Start New Relationships With Rose-Colored Glasses On


The last man I loved was a chronic — and I mean, CHRONIC — commitment-phobe. But because he also had so many awesome attributes, I overlooked that fact — for years. When it got to the point where we knew we had a solid connection and I also knew that he was too emotionally immature and unstable to establish anything solid and lasting, why did I stay…for as long as I did? Because I chose to ignore the blaring red flag that was staring me dead in my face.

Why did I do that? Because rather than say, "Shellie, you want a husband and he's terrified of commitment. So, even though he's a great guy, the two of you should probably just be good friends", what I told myself was, "He's got some great husband qualities, so I'll love him through his phobia of long-term commitments until he changes."

In other words, I saw only what I wanted to see. That's what rose-colored glasses are designed to do. If you don't want to keep dating the same guy over and over again, look at ALL of a man — not just the good parts.

6.The Thought Of Doing Something Different Totally Freaks You Out


It's amazing, the words we commonly use that we think we know the definitions for that we probably don't. Take the word "different". It means unusual and several and separate and not alike in character.

If all of the guys you meet are online, let a friend set you up. If all the guys you go out with, you sleep with after the fifth date, wait longer. If you only go for tall, dark and handsome, consider slightly shorter, cinnamon and hella cute. If your dating life has been going the same way ever since you can remember, step out and try something a little unusual.

I'm telling you, sometimes guys get a bad rap because we speak in generalizations about them. And that's because we're only dating one type of guy. If any of this resonated, even a little bit, stop dating the same man in a different body.

For the sake of your sanity, break your old patterns and try something new. There's no tellin' what kind of man is on the other side of your hamster wheel if you do. #realtalk

Featured Image by Getty Images.

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