How I Overcame My Addiction To Falling For And Chasing After Damage Cases

Hi, my name is Sabrina and I’m a recovering Damage Case addict.

What’s that you ask?

OK let’s back up. I’m going to share a story, my favorite way to illustrate a point.

After a string of mediocre dates that made me want to give up dating forever, a friend set me up with a guy named Kevin. Other friends warned me about him. He can’t commit … get goes from one girl to the next … he has issues. Well, they just said the magic words right there. I was immediately intrigued.

We went out for drinks for our first date and I was smitten. Finally, an interesting guy who is cool and fun and who makes me laugh. For once, an introvert like me isn’t counting the minutes until I can escape and retreat back to the safe confines of my apartment. I actually didn’t want the date to end. Now, this was something new!

But all good things must come to an end and when it does, he asks when he can see me again. We make a date to have brunch the following Sunday and I float home on a cloud.

In the week between our dates, I felt a very familiar feeling. I should have seen the signs. I had been down this road one too many times before. But of course, I ignored what I didn’t want to see and kept right on going. There was nothing tangible, it was just a vague feeling of uncertainty. I just felt like he was in complete control like this was all very transitory. Even though my gut instincts are usually on point, I asked them to kindly shut up and pushed them to the side.

So we went out again and it was great, at least from my perspective. But he left me with no indication that I would ever be hearing from him again. It was just a quick, “That was fun, have a great rest of your Sunday, bye!”

The sinking feeling started right there, but I ignore it because self-deception is every girl’s toxic best friend when it comes to dating. 

Days go by and no word. And then out of the blue, he calls, yes calls. We talk for a little and all seems great, I can finally breathe easy again. And just as I’m getting excited for him to ask me out on another date, and thinking about what days I’m free this week, he says, “So I think you’re really great, but I just don’t think we would work out long term. I just thought the right thing to do would be to call, especially since we have so many friends in common and I’m sure we’ll be seeing each other around. And I hope we can be friends.”

And I’m dead. Frozen. Horrified. Aghast.

“Um, yeah. You’re right. Thanks. Um, that’s so nice of you. Ok, see you around.” Picture me with my jaw smack on the floor. What??!!! How can that be? 

I am devastated and begin mourning the loss of a relationship that was two dates long (with one casual group hang out in between, so let’s say three dates!).

And it’s back to the drawing board for me… 

About two months later, I ran into him at a party. I knew he would be there and I made sure to look amazing. And it worked. We flirted heavily all night and somehow he ended up back at my apartment. We talked for hours and hours and maybe did some other things. I’m no dummy, even through my haze of lust and emotions and my need for validation, I could recognize what was in front of me: a damage case. 

The more Kevin told me about himself, the more I realized that he was exactly the type of guy I always seem to fall for. He was charming, charismatic, confident, fun, and I couldn’t have him because no one could. He’s the kind of guy that will always remain just beyond your reach, and that’s the way he likes it. He also had some deep-rooted emotional problems to deal with and some major commitment issues.

He is the type of guy I refer to as a “damage case,” a guy who has a lot of potential hidden under a pile of issues. The “bad boy” who needs to be saved. And like many women, I wanted to be his healer, to be the woman who inspired him to break through his walls and finally commit.

Damage cases are like a pair of super sexy shoes that are brutally uncomfortable. When you look at them they are amazing—they’re beautiful and sexy, and you have to have them. But when you wear them you’re in agony. Then you take them off and experience euphoric relief, the most incredible feeling. But this feeling doesn’t come from gaining something positive, it comes from removing something negative—pain. This experience is the same as dating damage cases.

They seem to be everything you want, so enticing you can’t resist them. But when you have them, you just feel pain and discomfort. Your stomach is in knots as you wait for the next text, or for a sign that he truly cares. Then he gives you some sort of indication that he does, and you’re ecstatic; you feel a rush of euphoria. But then he pulls back again and you’re back in those unbearable shoes. Then he comes back, and relief. And on and on it goes.

I knew it at the time, but I just liked him so much and I allowed my feelings to drown out my common sense.

We spent the morning together drinking coffee, laughing, and just acting like a couple. I tried to hold on to it tight because I knew when it ended, he’d be gone. But again, I didn’t want to admit it.

I was going out of the country in another few weeks and I thought for sure he’d try to meet up before then. Or at the very least send a text to wish me bon voyage. But no, I didn’t hear a peep. And while I knew I had no right to feel sad about this because he didn’t owe me anything, I felt incredibly sad, that gut twisting, nausea-inducing kind of sad that just makes everything seem black and hopeless.

Two months go by and while he’s still in the recesses of my mind, I try to move on and get myself together. And just as I kind of start getting there … he drunkenly shows up at my apartment one night at a small party I’m having. It wasn’t an official party. I had a bottle of vodka and some leftover birthday cake and invited some friends over after a night out to polish it off … and then somehow 20 people ended up at my house. And just as things were starting to die down, he staggered in totally off his face. And I wasn’t annoyed. I was elated.

Ugh, when will I learn? 

Immediately, I forget about my hurt, I forget how bad he is for me, I forget about the fact that he doesn’t really care about me because he doesn’t have the capacity to care about anyone in a deep way. Or maybe he does have the capacity, he just doesn’t allow himself to go there. I forget about it all and I take care of him. I give him water and bread to help him sober up. I help him walk because he’s totally unsteady on his feet. I end up putting him down on my bed because he’s in no shape for walking. As I try to leave the room, he grabs my hand.

“Please don’t go.”

His green eyes stare at me with a mix of wonder, awe, profound sadness, and a sheen of intoxication indicating his world is slightly out of focus. He lays on the bed horizontally, his long legs flopping over the side, as I lay next to him but kind of on top. He pulls me close and I feel that familiar comfort that always causes just a twinge of heartache. Heartache in knowing that it isn’t real, just an illusion. Like how his eyes, so green and serene, belie an inner world of darkness and defeat.

“I have to. I have 20 people in my apartment and you need to sleep it off.”

“Please don’t leave,“ he implores. “I need you.”

And there it was. He said the magic words. 

And I stay. I don’t care that outside my bedroom door are 20 people who need to be entertained and are now probably rummaging through my fridge and cabinets to find supplies to keep the party going. Whatever, it’ll be fine. It doesn’t matter, all that matters is him, in my bed, drunk to the point of near incapacitation, to the point that his firm guard is at long last down, exposing the pain he fights so hard to mask behind a sexy smile and aura of I-don’t-care. He’s here and he wants me to be here and despite what I know, I just can’t break away.

“Fine, I’ll stay for five minutes. What’s going on with you? Why are you such a mess?” He looks away, I almost catch the sight of tears forming but he quickly blinks them away.

“I don’t know. I wish I knew. Thank you for staying.”

He tries to kiss me, because of course he does, and I surrender. But fortunately, some semblance of self-esteem wakes up from deep inside, sobers me up, and infuses me with better judgment and I immediately break away.

“No. I can’t do this. I’ll stay and we can talk, but I’m not kissing you. And you’re not staying here tonight.”

“Okay,“ he says dejectedly. “But you’ll still stay, right? You’ll be here?” I sigh. I want to be there. I want to be there for him.

And there’s the ache again; he’s here, but he’s not mine. The moments of comfort are interrupted by the knowledge that he’s going to eventually leave and this will be over. He won’t want me past right here and right now. He’ll forget me when I’m not in his line of vision.

We end up talking for about an hour before the rescue party comes in to retrieve me. I can’t help myself from digging deep into his issues and I desperately wish they would disappear so we could be happy together.

I feel proud of myself that I don’t let him stay the night, that I have the foresight to know that him staying won’t change anything, that he will still be him. But I’m also sad. So sad that he’s someone I like, and he clearly has some sort of feelings for me, and we just can’t be together.

I think I’ll for sure hear from him after this, that he will at least thank me for taking care of him, but that never comes and why am I even surprised?

We have a few more of these incidents over the course of a year. Months go by without seeing each other, we cross paths, we either have an intense talk or we make out, I don’t hear from him and feel devastated, and repeat repeat. 

The final straw for me came during a weekend at the Hamptons. I knew it would be trouble. Me and him in that setting. I knew I was asking for it. So I did the mature thing and flirted with other guys to make him jealous. And he did the mature thing and scowled at me and gave me the cold shoulder and flirted with other girls. And we were both very mature and basically ignored each other all weekend.

There were not many words exchanged, but his eyes were always on me. Anytime I would talk to a guy I could feel his gaze, and all I had to do was look past whoever I was talking to and there he was … staring. And looking angry. And what right did he have to be angry? He could have me if he wanted, he just doesn’t want to! Or he can’t. Or he’s just too painfully damaged and I just can’t fix it.

At the end of the long weekend, I tried to talk to him about it. I asked if anything was wrong if he was mad at me.

“Nope. Why would I be mad at you?” But he said it in a way that said he was clearly mad at me and I just couldn’t deal anymore.

“Are you sure? You seem mad.”

“No, why would I be mad? I promise I’ll tell you if I’m mad,” and he walks away.

It’s not supposed to be like this. How have I spent almost a year of my life chasing after/pining for/moping over a guy I never even had in the first place? We went on two dates, that’s it! And he dumped me after those two dates. How did it come to this? 

It came to this because I was a damage case addict.

I couldn’t resist. He was my heroin. I knew it was bad for me but I couldn’t resist the high. The high of when things are good. Because with damage cases, when it’s good, it’s so good.

He wasn’t my first. But he was the last. The last in a long line of damage cases. It was cute in my late teens and early twenties, but maybe not so cute now that I was approaching 30. Maybe now was the time to figure out why I was only attracted to damage cases and totally put off by normal guys who genuinely liked me.

It occurred to me that I never once had a relationship where the feelings were mutual. It was either me chasing after a damage case (and even when you “catch” a damage case, you can never quite have him. Even when you’re in a relationship with a damage case, he’s not yours. He’s always just out of your reach), or a guy hopelessly obsessed with me and me trying to like him back to no avail.

I was just chasing a high, chasing the ego boost, chasing the validation.

Kevin was the catalyst for this realization. It had been a while since I had chased after a damage case, and I thought I had nipped that problem in the bud until he came along and got me all twisted like a pretzel. It was devastating on many levels, especially to my ego! I mean, I was supposed to know better at this point; I’m a relationship expert for crying out loud!

After a series of letdowns, of high hopes and thinking things would be different followed by crushing disappointment and feeling like a fool for once again thinking the same story would have a different ending, I made a firm resolution to end this cycle for good, to make a lasting change that would lead me to the kind of love and relationship that I really wanted. I was going to finally figure out why I kept going after damage cases.

I decided to sit down and ask myself some really tough questions.

What was I getting out of this relationship? Why was I so drawn to him even though I objectively knew he wouldn’t be a good long-term partner? What had he even given to me? I did a lot for him, but what had he ever actually done to show me he cared?

And the answer was nothing. Not even a thank you text for taking care of his drunken self! 

I was getting nothing out of this relationship except for quick shots of temporary validation whenever he seemed to reciprocate my interest, and that is just very sad. And then I realized that I am not the kind of woman who needs that sort of thing anymore. Maybe I did when I was younger, but I’m not that girl anymore, and I don’t need to repeat history in order to subconsciously mend some old wounds. I was done with the lack of self-respect and self-esteem that leads me down the rabbit hole and into situations that I know are far beneath me. Done settling for things that kind of look like the real thing, even though they are just an illusion. I was done dating the potential of what could be and ready to start looking at what was actually in front of me.

Next, I looked at why I kept going back to Kevin even though it was clear that the relationship was a dead end. I thought long and hard about what I was getting from him that kept drawing me back in, and the answer went beyond validation. I realized that with Kevin I felt less alone and maybe a little understood. Like me, he was a little lost and hurt, and that made me feel a little more OK in my own world of lost and hurt. There was a darkness to him that I just related to in a twisted way. And I also did genuinely think we could help each other.

I also considered what I was giving to the relationship (if you could even call it that) and why. Why was I so invested in solving his issues? Why was I so wrapped up in getting inside his head? The reason, I believe, is that getting lost in his drama was an escape from dealing with my own life and my own issues. I felt like I had a mission and a purpose and for whatever reason, that felt kind of nice. Damage cases are drama, and let’s face it, drama can be exciting and kind of fun … at least for a little while.

Once I saw the situation for what it was, it lost all appeal to me. Instead of feeling sorry for myself because I couldn’t get him to commit in the way I wanted, I felt sorry for him for having so many issues, issues that prevented him from committing to a great woman he had right in front of him. 

I spent the whole summer after the Hamptons debacle doing a lot of journaling, a lot of thinking, and a lot of getting back to myself. I took a break from dating completely, and Kevin just didn’t matter to me anymore.

And soon after I processed all of this and healed, my high-school sweetheart who I had never quite gotten over resurfaced. On our first date, I could tell by the way he was looking at me that he was in it, that he had graduated from being a damage case (back when he was 17) to husband material, that he was taking me and this seriously, and that I could trust him.

There was no hunt, there was no chase, there were no guessing games. I knew how he felt; I didn’t even have to ask, it was just so obvious. And I knew I was cured of my damage case addiction because the fact that he wanted me didn’t turn me off, instead, it made him even more appealing.

Fast forward a few years, we are now married and have a delicious toddler and a baby on the way! (And in case you’re wondering, Kevin, is still as single and afraid of commitment as ever … no hard feelings though, I still run into him here and there, and we’re friendly, albeit it’s always very awkward. But I can’t help but laugh to myself when I think about all the inner turmoil he caused … although he was also the catalyst that got me emotionally ready to be in a relationship with my husband, so maybe I owe him a thank you!)

Essentially the biggest epiphany of all that got me over the damage case addiction was this:

I want a partner, not a project.

I didn’t want a guy I had to fix. Fixing myself was enough work, why take on someone else’s baggage? I want someone who can take care of their emotional damage, who takes responsibility for it.

The reason I share this story is because I hope you can take the same path I did to a similar kind of happy ending. Remember, damage cases are a waste. Wanting a guy who doesn’t want you is a tragedy. Time is a precious thing to waste, so get to work and undo the faulty wiring that leads you to the guys who can’t appreciate you.

More than anything else, the path that leads to lasting love involves making yourself a vessel to receive love. If you only want guys who can’t want you back then you are blocked, so make the decision, right here and now, to push yourself to break free and clear away all the obstacles preventing you from getting what you truly want.


When I started dating my husband, a funny thing started to happen. All of a sudden I started getting closure with all these guys from my past. We didn’t have closure talks, per se, but I just started seeing things more clearly. I would randomly run into a guy who ghosted me and suddenly realize he has a horribly unattractive personality, or a guy I liked who was on the fence about me would confess his love, or I would just see the truth about all these damage cases.

It was happening one after the next and I knew the grand finale in all of this would be Kevin. I knew closure was coming, even though I didn’t really need it at that point because I had created my own sense of closure.

It happened a few months after I started dating my husband. I was at a friend’s birthday party solo and I knew he’d be there. At one point, a small group of us were standing around talking and a guy friend asked: “Sabrina, where’s your boyfriend tonight?”

Kevin turned white. Then he immediately and angrily said, “I need to go get a drink” and stormed away.

I didn’t see him again until the end of the night and I knew this was my chance.

I went up to him and said, “I need to talk to you.”

HIs anger and jealousy subsided and he was back to his usual cool as a cucumber, charming self. “Sure, what’s up?”

“Why did you storm away before when you found out I had a boyfriend?”

“I didn’t storm away. I just wanted a drink.” Wow, is he really this un-self-aware? He’s more of a damage case than I thought.

“You did storm. And you always watch me. Why are you always watching me? Like in the Hamptons. You kept watching me but didn’t even talk to me.”

“I don’t watch you. I stare at you because I’m attracted to you,”

“Why did you always act like you really liked me. Why were you always so flirty? You acted like you were in love with me and then you just treated me like crap.”

“I guess that’s just how I am with everyone,” he countered.

“I know. Because you don’t feel good enough, this makes you feel worthy. It makes you feel good to make people like you. Even if what you’re showing isn’t real.” OK, now he’s getting emotional. I need to dial this back.

“I guess you’re right,” he says, looking pained.

“Do you know that I really, really liked you? Like really?”

“You did?” He asks, genuinely shocked.

“I did. And you hurt me a lot.”

“I had no idea. I’m so sorry.”

“It’s okay. It wasn’t all your fault. I kept coming back. A lot of it was my fault. You were totally clear about where you stood, I just didn’t want to accept it because I really liked you.”


“Why what?”

“Why did you like me?” The bar is dark, but it seems like his eyes are welling up.

“I just liked you and I cared about you.”

“Why?” Now I feel on the brink of tears. Wow, he genuinely feels unlovable and unworthy. This poor guy. But now, unlike before, I don’t have a need to fix him. I feel bad, but there is nothing I can do.

“I just did. I liked everything about you, I liked hearing what you had to say and being in your presence. I just liked you,”

“I’m so sorry. I never knew. I swear, I never know.”

“It’s okay. It’s over now. I wish you all the best, I really mean that sincerely.”

And I walk away and that was that. And I meant it. I did and do wish him the best. I wish all my damage cases the best. They just aren’t mine anymore, I released them long ago and it was the best thing I ever did for myself. Thought Catalog Logo Mark

Sabrina Bendory is a writer and entrepreneur. She is the author of You’re Overthinking It, a definitive book on dating and self-love.

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