Throughout my dating history, there’s been one reocurring theme: my magnetic attraction to the tall, emotionally unavailable, illusive “top”. As I’ve grown older, I somehow segued from just dating emotionally constipated men, to dating ones who are openly jaded with no intentions or desire to work on their issues. Maybe I see something worth saving in them, or perhaps they remind me of how screwed up I am underneath it all. Either way, I have found myself subconsciously dating the same type of person over and over again to no avail. Being a great advice giver and a terrible advice taker, I’m hoping that this post will serve as a reminder to me the next time I decide to fall for another blissfully jaded soul.

Here are 5 things I’ve realized, the hard way about dating guys with baggage:

1. Taking time to examine his dating resume is essential. If he’s telling you that his past relationships have ended due to his lack of emotional capacity or intimacy issues AND he hasn’t gone to a therapist to remedy this….just know that you’re next. If he ever gives you the “…I’m known for breaking hearts.” line—believe him!! He might lie to you about sexting his ex, but one thing he’s telling the truth about is the fact that he’s probably going to break your heart. Trust me, I’m 2 for 2 on this. Stop, look, and listen—to every word that comes out of his mouth. Sometimes the truth is blatantly laid out infront of us but we still manage [or choose] to overlook it.

2. Be Prepared for an Uphill Battle. When he says he’s set in his ways…believe him. If you can’t be happy and 100% satisfied with the person he is on day one; walk away. The energy you’ll pour into trying to change someone could be spent learning a new hobby or getting to know someone else who suits you as is.

3. You may never be a big enough reason for him to fix his issues; and thats okay. This is harsh but it is oftentimes the truth. If someone doesn’t change for you, it doesn’t mean that you aren’t worthy, it just means that this is not your battle to fight. Don’t take on someone else’s demons if they aren’t willing to take steps towards confronting them. Hoping that you can be the ONE exception who breaks down their walls is cute, but there’s a very high chance that you just won’t.

4. This isn’t the 5th grade science fair; so stop taking on projects!! A man is not the same as a “fixer upper house” that you can just flip with a new paint job. Don’t go into a relationship with plans to remodel your partner into someone other than who they are. Trust me, it rarely ends well and is never fair to anyone involved.

5. Trust Your Intuition. When your gut tells you that you’re talking to a brick wall…you probably are. Once you feel, or get even the slightest hint that you’re not being heard, do yourself a favor and move on. Waiting on, requesting, or even demanding that someone change will only hinder your own personal growth and development. Sometimes people can only learn about their flaws on their own. Don’t lose yourself while trying to save someone else.


While every case is different, the above are just my observations based on prior experiences. I don’t believe that all jaded people are “bad” or intentionally selfish, but I do believe that their behaviors can pose a threat to the emotional well being of their partners if they refuse to make neccessary changes. Sometimes it’s the words that are unspoken which say the most. Don’t just observe what people say to you, pay close attention to what they don’t say. We all have our demons [trust me, I have my own LENGTHY list of issues] but the willingness to heal them and become whole is what makes all the difference in a relationship.


Listen, there are much less exhausting forms of self inflicted torture than chasing the heart of an emotionally vacant asshole.

Always remember that in order for a relationship to serve you, both partners have to be equally committed to each other’s happiness. Love should always be a two-way street.

Posted by:Anthony Black

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