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How to be Assertive Without Hurting His Feelings?

Anna Simpson
5 min readJul 13, 2019

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I couldn’t tell him, “we are done”

Credit to Vera Arsic

He was starting to get on my nerves. He was a nice guy and everything, but I felt I reached my limit. There was an initial spark of interest and curiosity, but after a few dates, I realised he just wasn’t the right fit for me.

I was dreading to go on a next date with him. We didn’t value the same things; we had different views and perspectives on life, we had way too many differences. In a word, there was a total mismatch. However, I didn’t want to hurt his feelings by directly saying, “We are done.” He was seriously into me.

He was a great catch as well: handsome, successful, kind. But at a heart level, there was no emotional connection, at least on my part.

Why were you dating him? You might fairly ask…

First of all, I didn’t want to hurt his feelings. I had my heart broken so many times by other men that I didn’t want to be the “bad guy” in that situation with him.

Besides, I was thinking, maybe, I was too picky. So, if I lower my standards of the ideal image of my Prince Charming, I could be happy. He was so nice and kind to me.

Being nice, I’m afraid, is not enough for love and building a serious relationship…

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Anna Simpson
Anna Simpson

Written by Anna Simpson

Helping people discover, articulate, and monetise their messages and stories, so they can get paid for who they are. www.anna-simpson.com/book

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