Dating the Wrong Men: Destructive Relationship Patterns to Avoid Series [Part 3]

We’ve made it to part three of the “Destructive Relationship Patterns to Avoid” series and the epic deep dive into all my past relationships! In part one we discussed dating anxiety. In part two we talked about the savior complex. And in part three we discuss dating the wrong men, pushing away the right ones, and losing myself in the process. If you haven’t read part one and part two, I recommend going back to read those. But if not, no worries. In the last post, we left off at my first boyfriend in high school and in this post we head into the rest of high school, and get all the way up to post college. 

Destructive Pattern: Dating the wrong men, and pushing away the right ones.

After Calvin, I felt free. The relationship and navigating through someone’s insecurities and tending to someone else’s feelings constantly drained me. My first experience with a “real boyfriend” reaffirmed my desire to not end up in a committed relationship. Commitment equaled suffocation and Calvin proved that to my teenaged brain. 

You’d think I decide to stop dating for good and enjoy my high school years, but not this one. Despite my commitment to anti-commitment, my teenage self kept finding herself in relationships.

So instead of avoiding relationships, I started dating the wrong men. I’d date boys I knew I’d be incompatible with. Unconsciously or consciously, I did it because I knew dating the wrong men t would mean never getting married. It’d be fun. I’d know when to get out since it’d be easy to see we weren’t compatible. That’s the point of dating the wrong men, right? So why the fuck not right? 


Great plan, little Chloe. 

What I didn’t plan for was actually falling in love with one or two or three of them..

Destructive Pattern: Losing Myself Within a Relationship… while dating the wrong men.

This pattern coincides dating the wrong men. It also coincides with dating anxiety, and the caregiver. My patterns stack up like a fucking seven layer cake.

In “The Parts I Always Lose”, I dive deep into the topic of how I often lose my sense of self in relationships. After dating Calvin, it became a permanent part of my dating experience. It’s something I struggle with to this day.

In high school and college I don’t think I ever felt a solid sense of self. I didn’t feel comfortable in my own skin. My identity was an ever changing entity ebbing and flowing as constant and unsure as the weather in Chicago. This fluid sense of identity caused me to take on the characteristics of the people I surrounded myself with, most notably the boys I dated. 

Sometimes it’d be little things like liking a band a boy liked. But sometimes it’d be big things. Like trying on a new religion. Or trying to change my whole wardrobe. Or trying to change my life goals.

Which when you’re purposely dating people you’re not compatible with… it’s a sticky scenario. I’d start dating someone who I knew was opposite of me and then I’d slowly start changing myself in order to be more compatible.

Curious as to how that worked out?

Like a flaming dumpster rolling off a cliff. 

Changing to Become More Lovable

I’d change and become whatever I thought the person I was with wanted or needed. Eventually I’d start to hate them for somehow making me feel like I had to change in order for them to love me.

Even though no one point blank asked me to change.

Sure. They’d make comments about the type of girls they wanted to be with and I would assume either (a) I’d fooled them into thinking I was that type of women, or (b) I’d make them fall madly in love with me by becoming that person, or (c) they assumed I was that type of woman and now I needed to act like it.

A boyfriend would mention he loved glasses on women because glasses make women look more innocent (gag). So I wore my glasses more and tried to act more innocent (double gag but also not hard since I was 16).

One told me he loved nerdy, shy girls because he felt like he could protect them. So I tried to be more delicate, less strong, and more in need of protecting (BARF). 

Another talked about how hot girls at Slayer concerts were, and I tried to become an emo-slayer-punk-chick who liked metal. Hot topic and all.

One loved Jesus and wanted me to love Jesus as much as he did, so I started going to church more and read the whole damn Bible.

Everything from my religion to my political beliefs to the color of my hair to what diet I was on– I was so movable. I was so flapable. 

The Root of the Pattern of Losing Myself while Dating the Wrong Men

I could come up with a hundred embarrassing real-life experiences where I’d change for a man to like me, but they all (save the Slayer dude) came down to making myself more girlish, more fragile and in need of protecting, less independent, less opinionated, more innocent, quieter, sweeter and more agreeable.  

Writing that sentence at 28 wakes the feminist dragon in me that would love to fly back to my past self, protect her, and shake some empowerment and sense of self into me while simultaneously bitch-slapping– I mean lecturing– all the boys who tried to shrink me.

The root of it is, I never felt lovable as myself, so I figured I’d become lovable by changing. I’d take things boyfriends would say, and decide it meant I needed to change in order to be their kind of lovable.

I have a few theories on why I did this and sometimes still do this:

Theory 1: I want to be the best at everything. 

I am competitive and have to be the best at most things. Even if being the best at something serves no greater purpose in my life or even if being the best at something means giving up something I actually love.

Like myself.

This translates into relationships because I have this eager to please personality that makes me want to be BEST partner, girlfriend, human, friend, co-worker, boss, etc. you’ve EVER had. It’s a little narcissistic but it comes from a place of insecurity. 

I want to be exceptional in everything that I do, even if that means changing who I am to make someone else feel more loved and appreciated. It permeates everything–I want to understand you more than anyone else has ever understood you. I want to love you more than anyone’s ever loved you. I want to treat you better than anyone has ever treated you.

And I want to be the best goddamn lay you’ll ever have. It’s bizarre and unflattering, but it’s true and pure ego.

Also, side note, this is why I like the Enneagram, because discovering my Enneagram type helped me realize this about myself, and knowing this helps me to stop unconsciously doing this. 

Theory 2: I never really knew myself and I definitely didn’t love myself. 

Only recently have I actually started to solidify who I am, what I want, and I’m just now making strides on accepting and loving myself. It’s hard to love ourselves if we don’t know who we are to begin with. The things I did know about myself, were things I didn’t like. So changing myself in order to be more lovable or likable never felt like a huge loss. 

This idea of not being lovable as I am is hardwired somewhere deep within me. Many times in the course of my life I’ve thought “This would work if I was a different person. I would be happy if I was a different person.” 

But instead of realizing this, understanding my shame, and then learning how to be myself, accept myself and then maybe even love myself– I spent years trying to change who I was in order to be who I thought other people wanted me to be.

Do I love me now?

Perhaps the better question is if I know myself. I can answer with 100% confidence– I know myself. I know who I am. There are certain things I know to the core I want, and there are some things I know I’m still figuring out. But even with that, I still have to remind myself not to get lost when in a new relationship.

Do I love who I know me to be?

Definitely more than I ever have before. Currently, I’m trying to learn how to love myself when I’m not achieving or being an achiever. It’s a big missing piece for me, and another thing the Enneagram made me realize.

So anyway. These are my theories, and I think they are quite likely both reasons for why I do this. My solutions to this particular aspect of my dating life? Recognize, label and redirect my behavior. I’m getting better but the habit of performing desirability is a tangle I’m still unwinding.

Anyway, moving on.

Dating the Wrong Men Continues

One of the most significant relationships for me in high school and early college was with someone who could not be more incompatible with me. We’ll call him Kyle.

Kyle’s a nice guy. Charming, outgoing, adventurous and caring but also very old-school, conservative, and has some very old-school ideas on what women should be to a man in a relationship. And I was head over heels for him. 

At the time, I didn’t know what I believed in, politics or otherwise, but his idea of a little wife in the home who’d be there to raise his kids, keep a house, and go to church on Sunday was NEVER going to be me. But for a minute I thought I could change all of that in order to be with him because you know why?

His attention and love felt so damn good.

He gave me unending attention, worshiped me for my looks and brain, and did thoughtful little things that made me fall hard and fast for him. I thought I could change into someone who’d want those things someday, and I tried, but failed miserably. And we did that young love thing– we dated on and off, hurt each other on and off, and tried again and again for almost ten years. 

I write more about that relationship in “We Broke Up, and It’s Okay” but in short and all the bad stuff aside, we were just a perfect example of two complete opposites trying to make it work long past when we should’ve ended things.

Side Effect of Losing and not Knowing Myself: Numbing Feelings

As I dated boys who were incompatible with me and effectively lost myself, I started shutting out feelings more and more as my battle with depression escalated. By college, I mastered the art of not feeling. I was drugged up on anti-depressants and anti-anxiety meds to cover the deep-seeded hate towards myself had started to fester. I stopped dating and instead took to drinking, occasional casual sex, and sleeping as much as possible. While balancing an overloaded schedule that included working 20+ hours a week, managing a commissioned art side-hustle, taking 24 semester hours in one semester, and trying to stay afloat as my depression and anxiety tried to swallow me.

Any semblance of self-love and self-respect completely tanked by the time senior year rolled around. I hated myself and used an over inflated ego to cover up for it. College is hard to begin with, but going to a big ten school hit me hard in my ego as I went from being a medium sized fish in a tiny pond to a minuscule fish in the massive ocean of an out of state public school. I bit off more than I could chew, and when I wasn’t the best writer or most creative or best at Spanish– I was a failure who at 21 years old might as well just given up. 

The achieving stopped, and I didn’t know how to like myself or be myself when I wasn’t achieving. 

So began a large spiral downwards.

Instead of working through my feelings of worthlessness, I started seeking outside validation from anyone who would blink in my direction.

I started binge drinking (while on a cocktail of anti-depressants and anti-anxiety meds that you are NOT supposed to drink on) and binge eating until I’d make myself ill. The pattern of choosing the wrong men intensified in this period of my life. Over and over again I entered one-sided relationships with people who used me. I let it happen, and believed I should take what I could get. It turned into such an ingrained normal that dating people who showed actual interest, affection or genuine interest felt more uncomfortable than being with people who forgot my number until it was 2am on a Saturday. 

It was a really dark time for me, and a time where I blamed the world for my problems and took no ownership of my own life. I thought it was over, it being my life and dreams and for a little while, I kind of gave up on who I thought I was and wanted to be. And after going to three different psychologists, two counselors and all the different type of anxiety meds– I totally gave up on myself for a while because I believed nothing would help me. 

When the Veil of Depression Started to Lift

Once I graduated college and moved home for a bit, I started to stabilize. I’d given up on most expectations of myself and achieving anything, and because of that I was able to start taking care of myself. 

Around the same time I dated my first truly nice guy, David, who showed me unconditional love from the very beginning. Even when I felt the most unlovable. In that relationship, which only lasted half a year, I learned what it was like to be loved exactly as I was. For the first time since Calvin, I dated someone who also felt like a friend. It transformed me. Gave me a foundation to change and grow.

But I wasn’t ready to love him back in the same way. And the lives we wanted weren’t all that compatible. Even so, I am forever grateful to David for being the kindest heart I’ve ever had the privilege of dating. His support and constancy helped me grow in a way that outgrew our relationship, but to this day I look back on that relationship as the healthiest relationship I’ve had. 

Diverging Paths

In the end, we wanted very different things. He was happy living in our hometown, staying at his job, and living the small town life that I felt suffocated by. We would have both sacrificed things we knew we shouldn’t and couldn’t in order to be together. 

So, I moved to China. And he stayed. And maybe that was one of the only times I didn’t try changing myself for a relationship.

Now you’re probably wondering– China? What the fuck, Clo? Where did that come from?

One of the things I lost about myself while slipping into a deep dark haze of depression, is since I entered high school I wanted to live abroad. When I got out of college with $60k+ in debt and a job that paid $14/hour, I felt like that dream had been stamped out of me. I couldn’t save up to go to China. How could I live in China on a salary of $1.2k a month? I had to pay student loans that cost me almost $800 a month!

But being home helped me find some sense of self. And being with David gave me the confidence to do what I truly wanted. So I started budgeting. I started saving. And more than anything else, I started believing I could actually do it.

A year after graduating college, I packed my bags and left for Wuhan, China. Where I continued dating the wrong men.

But we’ll get to the China years in the next post. 

woman thinking about how to stop dating the wrong men

Your Turn

Do you struggle with losing yourself in a relationship? How have you handled it? What patterns have you overcome and what patterns are you working on? Share in the comments below to join the convo.

Read part four of the destructive relationship patterns to avoid series: ignoring relationship red flags.

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7 thoughts on “Dating the Wrong Men: Destructive Relationship Patterns to Avoid Series [Part 3]”

  1. I’ve lost myself in past relationships, but I realize now that even when I want to retreat into my partner or get lost in them that I have to keep doing the things I love because that’s what attracted that person in the first place. If there’s something that I said “oh I want to do that”, I’ve made the commitment to myself to do that thing, whatever it is. When you change or get lost in a relationship, I realize that it makes the connection fizzle out because you get lost in the day-to-day and you’re not enriching your life at that point.

    For me, I’ve been saying that I want to compete in CrossFit comps, keep traveling to participate in fitness events and create podcasts, and take a pottery class. I just have to do them and have my own sense of accomplishment, keep meeting people and discovering myself because it keeps things interesting and my partner would want me to have my own thing.

  2. Hoooo boy have I been here – in therapy 2 years now for codependency and am finally, FINALLY seeing the light at the other end of the tunnel. I did a lot of EMDR as well and it actually released a lot of things and jumpstarted a dating journey with a bunch of poor dating decisions (I had never dated prior to EMDR, having gotten divorced before starting therapy)…But I will say that these experiences were the only way to apply theory to practice, so to speak, and learn through experience what felt right or wrong. I suppose this is how we all learn, but it can be hard when you’ve had past trauma or dysfunction. So hard to see the red flags for what they are when you’re not used to respect/love/kindness in the first place. Thanks for sharing your experiences.

    1. Yay for seeing the light at the end of the tunnel! It’s hard work but totally worth it. Sending you a big ass hug as you continue on that journey! And thank you so much for this comment and vulnerability. And agree– I felt like I had to learn how to feel my gut– and the only way to do that was through experiences!

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