Honesty: helpful or hurtful?

I have a topic on my mind that has been bugging me all day! Which is better/worse: to be nice & don't tell a person something because it may hurt their feelings or to just be honest with the person & not keep them wondering in the dark...?
I have been on both sides of the spectrum, so I do know this is a tough decision. However, I do think honesty is always better. I've been honest with people just so they don't have to feel clueless or "waiting", I've been told my flaws as well, which at the time didn't feel so nice, but I now know its better then wondering. But most of the time I'm left in the dark, which I hate.
I know I've said it before, but in the love & relationship department I just don't have any luck, unless bad luck counts! Most stories start off with "so there's this guy I like/liked for a while...." and ends with "he says I'm a good friend/ one of the guys..." or "he always has excuses not to hang out ..." the story is always the same, but I guess I just am optimistic or maybe just plain stupid.
So, in the end, I guess what I'm really wondering is if I really want to get left in the dark/blown off time after time or do I really want to hear whats wrong with me/why I'm just not appealing ...? Is there really a good answer? I guess only time will tell!

A dose of reality

So I had a good friend of mine say something That was horrible to hear, but the honesty I needed. "Between all you do to stay busy, that's why you're still single." Stings to hear or even say, but could there be truth in it?
I do stay busy, 3 jobs, 2 schools, 1 kid, 1 house to finish... no sleep! This is my way of life & as I always say it keeps me out of trouble, but is it possible this could all be a defense mechanism? 
No one will ever hear me say That I like to stay this busy, to stay away from my child so much, but I do it to keep us going. Our lifestyle is pretty set in stone (I.e. buying house, etc) so I'm not going to have Faith suffer & change her ways just because I'm going to school. I go to school so much to try to better our lives, so that she wont have to know how hard life can be, but lately it feels like I'm running 100mph yet going nowhere. 
I dream of a better life, but I guess I always see it as a better life for Faith & I... is that bad? Is it a sign? Who knows, been on my own so long I don't even think I'd know what to do if I had someone else around.