I try not be a harsh. I'm a nice guy. I think there's also the issue of intimacy level. If your best friend asks you something, anything really, you owe it to them to be very honest, possibly somewhat harsh if necessary. Now, if its an acquaintance, or even a good friend who's kind of on shaky ground emotionally, soften up.
It also depends on the person receiving the information. Some people respond to a bit of toughness, or at least do in certain situations; lots of other people need a gentler touch, like in the example reba gave you.
I think a lot of times "tough love" is used to justify behavior that is anything but loving. I've been on the receiving end of some "tough love" from family members that was really just aggression and harshness disguised as "tough love" or some other pop psychobabble nonsense.
Keep in mind that, yes, we're called to tell the Truth, especially as it pertains to absolute Truth--the Word of God. So, for instance, when one of my friends says "I want to sleep with ____, what do you think?" I say "I think you should try keeping your clothes on," because as a follower of Christ, I owe everyone the Truth of God. But we're also called to be meek and humble, slow to speak and eager to listen. We're to die daily, and being harsh without good reason feeds the flesh.