Dear Herb,

It Depends On What It Is You Have To Tell Her

This question cannot be answered as a matter of fact, because it all depends on what type of news you have to tell your girlfriend.

Some Things You Should Definitely Tell Her, Some Things You Shouldn't

If you wanted to tell her that she was fat and you know it would hurt her, and if she is happy the way she is, then you shouldn't tell her. If your news is something like this: you don't like her anymore and you have fallen in love with another woman; then no matter how much pain that causes, it will only get worse as time goes on.

Some Things Require A Judgement Call

If the news is somewhere in between these two extremes, for instance: the boss who she thinks loves her really despises her, that becomes a judgement call.

On one side of the fence there's the fact that you aren't a part of that part of her life, and so you should just stay out of it because you don't know the details. The other side is that you do tell her because you don't want her to suffer in the long run.

If You Do Tell Her, Ease Her Into It

If you do tell her, be prepared to deal with her answer.

All in all, if the news is going to hurt her but has no substantial value in her life, you probably shouldn't tell her. However, if the news could change her life for the better, then maybe you should tell her. Just let her know in a not so harsh way – don't just throw the news at her. Ease her into it.

Hope I helped a smidge! =)

– Dakota