I can think of only two main reasons you might be reluctant to say what you want to say to someone you respect or care about: One, you are going to hurt his or her feelings and two, you are afraid s/he will get angry.  All the other reasons I have heard over the years can be considered sub-groups of causing anger or hurt feelings:  it may cause “another” fight, you are going to have to follow up with an action you are reluctant to do, you don’t want to see her/him cry, and doubtless a few more.

If you feel what you have to say needs saying then there are a few ways you can make it easier, though probably never easy, on both of you.

*  The method of delivering what you have to say is important.  A post-it, a text, a phone message, are all cop-outs.  If this news is likely to cause upset and the person to whom you’re talking is someone with whom you have a relationship say it in person if at all possible.  “You’re fired”, “The test was positive”, “Our relationship is over”, “Your cat was run over by a car” are too important not to be said face-to-face if at all possible.

*  Consider practicing what you have to say.  Write it out and edit it if you must to find the gentlest way you can. You might even practice with a close friend until you have it down.

*  Choose a time and place that is private and open ended.  Not before sleep.  Not before work. And don’t set the other person up to worry about it all day.  Remember grade school when the principal told you first thing that she wanted to talk to you after school?

*  Don’t protect yourself by saying it in a public place, hoping the other person will be too embarrassed to make a scene, unless you are worried about physically protecting yourself. Then a public place or having someone with you is a good idea.

*  Try to give some examples if you are delivering some bad personal news such as “I’m worried about your health. When was the last time you saw a dentist?  Your breath has not smelled fresh lately.”

*   If you don’t want this communication to end your relationship assure the other of your desire not to do so, only to change something between you.

*  If you want to soften what you have to say touching the other person while you talk may be helpful.

Hearing unpleasant news from you face to face may be harder on you but it may be easier on the other person and you both will eventually respect you for doing so.