Another post wherein I forgo the wise-assery and answer your questions seriously but in brief -- become some questions aren't that complicated. (Not to be confused with my award-winning* Quick Answers To Your Quick Questions blog posts.)

Should I e-mail a guy to make it clear I'm NOT interested in him?

It would be better -- and more effective -- if you told him in person. That way, you'll know he got the message, and he'll know you are serious.

What does it mean when a guy you f*ck every once and a while talks to you like you're a friend and constantly talks about how hot other girls are?

It means he considers you a FWB and nothing more.

Are there circumstances where cheating is okay?

Nope.

I just read an answer you gave to a question about college; that college are the years to learn about yourself and be free and try new things? I go to community college, not transferring to a real college, and I live with my parents. Is it the same thing?

Not really. College isn't all that different from high school if you still live at home. The freedom and new experiences I wrote about occur largely because you live away from your parents and can come and go as you please without having to answer to anyone. If you live at home, can you stay out all night? Sleep till noon? Bring someone back to your room? Go away for the weekend without having to tell someone where you are? You'll grow and experience new things at community college, but it doesn't really compare with living on campus.

So I've been out on a few dates with a few guys this week. I'm still figuring out if there is potential with either of them. How long do I have to choose? Not looking for drama.

There's no rule; take as long as you need. If either of these guys is drama-prone, it will happen whether you date him for a week or for six months.

If a guys says he doesn't know what he wants and needs to think about it, does he really mean it, or is he trying to let me down gently?

Does it matter? If he has to convince himself to be with you, move on. He could string you along for months with that crap. Find someone who really wants to be with you.

What are the odds for a side chick to become the main chick after she successfully ruins his primarily relationship?

Very bad, hopefully, because she sounds despicable.

When should you tell a guy about past mental health issues? I've struggled with depression in the past, but have been happy and healthy for a while now. I'm not sure when or how to bring it up with my guy.

There aren't many people who haven't struggled with depression, so I doubt he'd be surprised at the news. But, yes, timing is important, and this answer might help.

What does it mean when a man has slept-over (cuddled, kissed, etc) at your house over 10 times and still hasn't slept with you?

It means he likes you but isn't sure you want sex with him yet, so he's trying not to be pushy. If you're ready to get it on, tell him... or show him. Initiate. He'll be all over it.

My guy friend (who I kind of like) came to visit me and made me angry because he was belligerent the whole time and left without telling me. I have not been answering his calls or texts. What is a better way to handle the situation?

With honesty, not silence. In this situation, silence solves nothing. Answer his call or text and be honest -- tell him he was a drag during his visit, and ask him why. If you're still interested in him, say so, and if you're done with him, say so.

We've been on a two dates and I'm not feeling the magic. He's theoretically perfect. Do I give it a few more shots or jump ship?

My gut says jump ship, but maybe the guy is just the nervous type. Can you stand one more date with him? Theoretically perfect is meaningless, by the way. The Titanic was theoretically perfect. The Normandy invasion in World War 2 was theoretically perfect. Sometimes "theoretically perfect" works out, sometimes it doesn't.

My bf has recently been taking medication for high blood pressure. An unfortunate side effect is that he can't achieve as hard an erection. He has been very attentive to my needs but has been shy about letting me take care of him, but I want to reciprocate. Is it possible for a man to orgasm without a full erection?

Yes, it is possible to climax without an erection. It won't be the greatest he'll ever have, but it's better than nothing. Has he talked to his doctor about this? There are probably other medicines that can help with the side effects, or he could take an ED drug like Viagra or Cialis (though he should check with his doctor to make sure they aren't contraindicated with his blood pressure meds).

I met a guy at a concert and made it very clear I was interested. I got his number, and texted him so he'd have mine. Should I make an attempt to pursue something and how long should I wait to hear from him before I do so?

That depends on you. You've already shown interest by texting him. If he hasn't replied within a few days, he's probably not interested. But then, texts don't always make it to their intended targets, so you could call him if you're not ready to give up yet.  If he doesn't answer or doesn't reply to your message, forget him.

My parents are fighting and during my whole life they've been the rock that was stable in my life. I don't know what to do anymore, how do i get them to stop?? It's breaking my heart.

I know it is, and I'm sorry to hear it. I watched my wife go through the same thing when her parents split up, and it was awful. Unfortunately, there's nothing you can do. You can't make them stop. They have to work out whatever they are working out. All you can do is support them both. Hopefully they won't involve you in their fights. If either of them starts bad-mouthing the other to you, refuse to take sides and insist that they stop putting you in the middle, because it's unfair. This is their mess to figure out, and the more you can stay out of it, the better. Love and support, yes; involvement, no.