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Does Your Date Challenge You or Are They a Jerk?

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I’m the kind of person who has always enjoyed a challenge – especially in my romantic life. I used to think that in order for a relationship to be worthy it had to be fraught with challenges, adversity and emotional pain. I looked for relationships that played out like a 1990’s Mary J. Blige song before Mary decided on “No More Drama.”

I thought that in order to be “challenged” in a relationship, I needed to endure all kinds of negativity. I didn’t understand that being “challenged” could come from a place of kindness – or that it should. Consequently, I dated a lot of jerks and people who were utterly wrong for me.

For example, when I was in my early twenties I dated a guy who would always criticize the way I dressed, the friends I had and the music I listened to (among other things.) Whenever I’d defend myself or tell him to cut it out, his reply would always be “I’m just telling you these things for your own good – so you can become a better person.” FYI, insulting someone’s appearance (“You should really get to the gym”) isn’t going to make them want to improve themselves, it’s just going to make them feel sad and insecure. Hindsight is 20/20. I can now see that this guy was clearly an unhappy person, looking to project his insecurities on other people. He was a textbook jerk.

I’ve since learned that it’s good to date someone who challenges you, but that sense of challenge has to come from a good place. So, how can you tell if the person you’re dating “challenges” you or is just a jerk? Here’s a few thing to think about –

  1. Do they encourage you or are they just trying to change you?

Someone who challenges you, encourages you to live up to your potential. A jerk just wants to change you. There’s a huge difference between loving encouragement and trying to coerce someone to change in order to suit your needs. The confusing part is that jerks often hide their true intentions under the guise of encouragement. They may sound encouraging (“I’m telling you these things so you’ll become a better person”) but really, they’re trying to break down your sense of confidence by letting you know that they don’t really like the person you are now (then why are they dating you?!) Someone who challenges you already likes you exactly the way you are and truly wants you to live out your potential.

A challenger: “You’re such an awesome illustrator. Have you ever thought of working on a children’s book? You could totally do it! You should talk to _____.”

A jerk: “You know, if you went to the gym more often you might have a better ass. With enough squats, you might even reach a Junior Kardashian level.”

Feel the difference? Remember that your gut never lies. A jerk will always make you feel like you’re not quite good enough. Whereas, being with someone who challenges you in a healthy way will make you feel happy, inspired and excited about the future. You should also feel like your partner supports you and has your back. Jerks want to knock you down. Challengers want to build you up.

  1. Do they challenge your opinions or do they critique your character?

You know what’s boring? Someone who always agrees with everything you say and do. Snore. Part of being with someone who challenges you is that there’s always room for debate in the relationship, which keeps things interesting. However, it’s important to note that there’s also a huge difference between discussing different ideas and attacking someone’s character. Are they critiquing your idea or are they critiquing you?

A challenger: “While I get what you’re saying, I just don’t agree at all that Hillary isn’t a good leader. Look what she did with peace in the Middle East. Have you thought about ______?”

Jerk: “You’re dumb and stupid to think that. This just goes to show how little you know about anything.”

See the difference?! People are allowed to have different ideas. It’s healthy! While you may not see eye to eye on everything, you should still feel cared for and supported by your partner and not like they’re always attacking your sense of being. If that’s not the case, you’re dating a jerk.

  1. Do a gut check. How do you feel?

Our intuition offers some of the best dating insights. If you’re dating a jerk, you’ll feel it. You won’t feel happy and inspired. Instead, you’ll feel insecure, belittled and defensive – like you never quite measure up. That’s no way to live. So, if you’re still unsure about the relationship, check in with yourself. How do you feel when you’re with this person? If the answer is “crappy about myself” – you’re dating a jerk and it’s time to move on.

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