Dating Advice for: “I’m Only Attracting Damaged Men”

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

Jackie, I need dating advice. I’ve been divorced for two years. I cheated but my ex left. I am dating but only attracting damaged men. Recently, a man left me again after two months. I’m so heartbroken and want to know what I did wrong. He and I are never going to work out, we are totally different people, but I so miss him. I feel so down and crying non-stop.

I always feel the need to state that I have no training in psychology, so please take my advice as a friend, not a licensed therapist. With that, here are my thoughts.

First, why are you saying “I want to know what I did wrong?” In other words, why do you assume he broke up with you because you did something bad or wrong?

Dating can be very difficult in the sense that when people date, they are spending time with a person to determine whether or not that person is a good fit. So, they date that person until they decide for some reason, they don’t want to anymore. That can be anything. Maybe in their heart they just can’t picture a future with the person. Maybe they thought they were over their last relationship and they just aren’t, and it’s impossible, in their mind to start something with someone else. Maybe they meet someone else unexpectedly and they want to also date that person.

So, dating means taking risks that you might get hurt, and the hardest thing to do is to not take it personally if it doesn’t work out. But, unlike in a business situation, it IS personal! So, how can you NOT take it personally? It’s hard. I get it.

But, just because you weren’t the one for this guy, that doesn’t mean you aren’t the one for someone else. For one reason or another, he just didn’t see it moving forward. That doesn’t mean there is anything wrong with you, or that you said or did something bad or wrong. It was just wrong for him. One of these times, you won’t be wrong for someone else.

The other thing is, it was only two months. I know it feels heartbreaking right now, but trust me, the second you meet someone else you are interested in, you won’t even remember his name. Dating means taking risks, putting yourself out there and handling rejection. Not easy, but that’s what it is.

Now, onto this thing about “attracting damaged men.” What does that mean and why are you doing it?

I’m going to take “attracting damaged men” as meaning these men are older, divorced and possibly suffered a bad breakup (I guess all divorces are bad breakups.) Because they are “damaged” maybe they exhibit behavior that makes it difficult to sustain a healthy romantic relationship. Examples include, substance abuse, cheating, emotional abuse, depression, bitterness, fear of commitment. (By the way, this these can apply to women, as well.)


6 Potential Reasons you Might be Attracting Damaged Men (or Women)


  • Low self-esteem. In my opinion, people with low self-esteem, who don’t think they can attract someone better than a person exhibiting these bad behaviors tend to go after damaged men (or women.)


  • You don’t want to be alone. Some people can’t stand not being in a relationship. They view being single as lonely and sad. (Which is my theory for people who rush into second marriages). And so, they settle for someone they know isn’t right, because in their mind, it’s better than not having someone.


  • You’re stuck in a pattern. Here’s an example. A person’s father cheated on their mom and they knew it growing up but no one talked about it. Then let’s say they married a man who cheated and they got divorced. Now, they get into relationships with guys who cheat, because that’s all they know. There is a subconscious comfort in the familiarity and they don’t realize that they need to break this awful pattern and attract a different kind of man.


  • You don’t like or love yourself. A lack of self-love almost always leads to people dating men (or women) who aren’t right for them. Maybe they are even punishing themselves by going after people who don’t treat them well or make them happy.


  • You subconsciously don’t want to be involved with anyone. People who don’t want to be in a relationship will often go after men (or women) they know they aren’t ending up with because it’s safe. Maybe they get involved with someone who is much younger or much older, or someone just out of a long-term relationship, or someone of a different cultural background, because it’s safe. Or, they attract a big drinker, and they continue to date him for a long time because in their mind, they are saying “this guy is great to date, but I would never marry someone who drinks this much.” So, if there’s no way it’s going to turn into a marriage, and in their mind, they don’t want marriage, that works out perfectly.


  • Isn’t every man (and woman) damaged in a way? I’ll come right out and say it. I’m damaged. That doesn’t make me a bad person, or a person who can’t have a successful relationship in the future. But let’s call a spade a spade. A divorced person (and really, anyone who is older and who has lived a life) is in a way, damaged.
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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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