How to be Assertive Without Hurting His Feelings?

Anna Simpson
5 min readJul 13, 2019

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…

The biggest reason why I was with that guy I clearly wasn’t in love with was my fear of being alone. I was dreading lonely nights on my own more than I was dreading going on dates with him. I was single for a long time and I didn’t like that state.

I wanted to give him a chance to impress me, to sweep me off my feet, to make me fall in love. But it wasn’t working. There was just no chemistry going on between us.

No matter how many times I tried to persuade myself he was a good match, my logical mind would not connect with my emotional mind.

You can’t force love, I guess.

My philosophy was “a bird in the hand is worth two in the bush”. I wasn’t confident enough to say “no” to something average to clear the space for something amazing.

To be really honest, deep inside, I didn’t believe I was worthy of something amazing. And I was convinced — great guys are quite scarce out there, so I’d better…

Anna Simpson

Helping people discover, articulate, and monetise their messages and stories, so they can get paid for who they are.