How to be Assertive Without Hurting His Feelings?

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 hang on to him, because I will risk being alone for the rest of my life.

I know that was quite pathetic.

I had an idea of my “Prince Charming”, but I didn’t believe it was possible for me.

There are so many women out there who stay in unfulfilled relationships out of fear of being alone and out of scarcity mindset. They settle for less never realising there is so much more to life, love and relationships.

The truth is: there are enough great men out there who are looking for love and meaningful connection.

You can attract your Prince Charming and create your dream relationship with him as long as you believe it is possible.

Now, let me be very clear, by Prince Charming I don’t mean Bred Pitt, George Clooney or any other sort of unrealistic vision. Besides, my idea of Prince Charming will most likely be different from yours.

So, why do we limit ourselves in what we believe we can and cannot have…

We shouldn’t settle just for a nice or good enough guy. Call me a romantic but I truly and passionately believe we deserve to live our big dreams. We have the power within to make them happen.

Why settle?

Coming back to my Mr. Nice Guy, one day I was sitting in the park enjoying the light Florida breeze and I was thinking… I tried to imagine our future together, but I couldn’t.

I was never fully into that relationship. I wasn’t always available and I wasn’t as committed as he was. I kept my distance but I was close enough for him to be attached to me. I was giving him hope without the intention to follow through on it. Although I never made any explicit promises, he had expectations.

I realised, I was being selfish with him. I was using the guy to cover up my inner fears.

It was time for me to show my assertiveness and rip the Band-Aid off. I had to tell him, “We are done.”

Treat people the way you want to be treated. I wouldn’t want someone to be with me who wasn’t in love with me.

Men have feelings as well. They can be hurt as well.

I had to wait the right moment.

At dinner, I summoned my courage and said to him, “We have to split up. I appreciate you as a person and I think you are a wonderful man, but I am just not ready for our relationship to evolve.This is not about you. It is about me.”

I tried to be as gentle as possible.

He was listening to me but it seemed he didn’t grasp the meaning.

“What would you like for desert?” he just said.

That’s his response?!

Did he not hear me correctly? Or did he choose to ignore me?

“I want to break up with you.” I just said.

The evening was horrible. I felt so guilty.

Obviously, he couldn’t handle the rejection very well; so ignoring it was his armour.

He switched the topic by starting talking about his new project.


I felt irksome but again, I didn’t want to hurt his feelings, so I tried really hard to show as much understanding and support as possible. He was clearly hoping to make it work.

There were many reasons why there was a mismatch between us. One of them was he couldn’t listen. Even if he did, he didn’t understand me or pretended not to understand me. Just like when I told him I wanted to break up.

When the evening was over, I felt relieved and really good about myself.

Always choose integrity in life, even when it is uncomfortable or even when it hurts.

You have to be assertive in your life and your relationships.

Being assertive doesn’t mean being aggressive and neglectful of other people’s feelings. It simply means openly expressing your desires, wishes and opinions without feeling guilty about them.

You have to say “yes” to you even if it requires saying “no” to someone else. It doesn’t make that person unworthy. Your ability to say “no” to what detracts from you strengthens your self-worth.

Your life is precious; so don’t waste it with someone you don’t care about. It is not fair to the person concerned and it is not fair to you.

Ukrainian by birth, American at heart, world traveler, who dares to go after her ambitious goals. Empowering women to achieve their dreams

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