Answers after the break.

1) Depends on your own orientation and the gender combination.

If you’re both the same gender and of differing orientations then just make sure you’re both on the same page.

If you’re both the same gender and the same orientation, I assume the issue would be if you’re already in a relationship or not looking for one with them. Again, make sure you’re on the same page.

Under these circumstances, to an extent, you have to not worry about their feelings too much. They need to know nothing’s going to happen between you two. There can’t be any misunderstanding. If they get offended, it’s better than some of the alternatives.

Now here’s the less obvious one, if you’re differing genders, don’t treat them like one of your own. A gay colt is not a filly; a gay filly is not a colt.

And don’t trust them with gender specific things either. You’d be surprised the loops some ponies will jump through to be able to walk in on somepony showering…

2) Like my grounding is even that bad.

3) O~h no. I’m not getting roped into that trick. I’d rather not be suddenly forced to answer to every mother in Ponyville.

Abstinence.

4) Pony Joe.

…

I’m just messing with ya. But out of everypony in Equestria, would you have ever thought of that?

5) Depends which one, I guess. They’re all exes for a reason, though.