Hey Michael,

Before I begin on the matter of importance, I just wanted to say that I enjoy your blog very much. It’s gotten to the point where I check it everyday to see if there are any updates. 🙂

So, I was hoping maybe you could help me out with some advice. I’ve been seeing this boy…his name is Michael too. We started talking on an iPhone social networking app in January. Things were going great, and we eventually started dating. He is 18 years old. and I am 21. Our relationship only lasted one month because he ended up not wanting to be in a relationship with me. He said he still had feelings for his ex. So we stopped talking for about 2 months after our breakup. Now he is texting me a lot and we actually went out to dinner last week so we could talk things out and be on good terms. It all went great, we laughed and talked seriously about how thing ended between us. He tells me now that he really still likes me and thinks about me all the time. He told me the other day that he wants another chance with me. I’m not sure if I should tell him have it because I feel like he still has feelings for his ex and things will just be the same as last time. He will also be leaving for college in the fall…in another state. I just dont know what to do really. I like him, I think he’s a great guy. What do you think?



Thanks for writing in.  You’re sweet and kind, and not a douche.

At least, I get that from your letter.  Am I right?

So this guy wants you back eh?  Okay.  You seem to like him.  So maybe let him have you back?  A little.  But hey, make it difficult for him.  Make him prove that he’s not just trying to see if he can get you back out of some emotional existential boredom. On the other hand, don’t make it TOO hard for him – gay people are frequently emotionally ADD.

You think he still has feelings for his ex?  You’re right. He does.  That’s how love works.  You don’t ever stop loving someone, once you fall in love with them.  You just find ways of muting it, when it’s over.

So, okay,  here’s my advice:  Do it.

Let yourself fall for this guy.  Let yourself love him.

But only a little.

He’s leaving.  He’ll be gone in a few short months.  That sucks, but there’s a power to that.  It means that even if he doesn’t act like a douche about his ex, he’s still going to break your heart by leaving.  So, either way, it’s going to hurt.


You like him.

You should fall for him.  You’re 21.  He’s 18.  You’re supposed to be having epic romances.  Let yourself.  See where it leads?

You will heal if he hurts you.  Let him.

Do you want to go through life as an emotional daredevil?  Of COURSE you do.  You will heal if he hurts you. Always keep one eye open and know this might be treacherous. I love you.


Kinda Awkward,

Okay so im 18,and ive had sex a few times..i bottomed now for the 4th time and cant help but feel that its not for me. I hate to say it but, it just feels like im pooping :p

if it wasnt for this constant feeling of pooping when he fucks me,i think i might like it…I know what ur gonna say, poop before, but i do and i still feel it..then im worried ill poop.
is every man suppose to like anal sex? I feel like im a bottom, but i just dont know what all the fuss is about getting fucked. Is the moans and growns in porn, moans of pleasure or just discomfort?.will it become more enjoyable with practice?all i want to do when im with  guy i like is to please him,how can i get around anal sex?How can i keep a guy i like without letting him in?

-Awkward and lonely

p.s. whats ur views on unprotected sex
I bet you’re a beautiful guy.   I know you are.  All Gay people are beautiful and perfect, because all people are.  I believe that.
Here are a few things to consider.
1) Maybe you’re not a bottom?  Hey.  When you’re young and gay and pretty?  EVERYONE wants to fuck you.  But, maybe you’re not a bottom?  That’s a possibility to keep in mind.  Maybe you’re a top?
Or maybe you’re one of those weird Gays that only likes oral sex?  I love those weird Gays!
2) However, it sounds like you want to bottom, or try to learn if you are a bottom. In which case:  Keep Doing It.  Let yourself try it… oh I dunno…  ten times?  If after ten times bottoming you think it’s a nuisance, then try finding a cute boy to top.
I want to ask – are you cleaning out?  Are you giving yourself an enema before you let someone penetrate you?  That can make all the difference.  I know lots of bottoms that fuss about whether they’re going to poop everywhere.  Most of those guys just clean out, so the sex is not filled with… er… smudges…
(if you need more information about this, awkward, just email me and i’ll be more specific)
Here’s my advice:  I frequently think Gay men have the short end of the stick.  We are a cultural bogeyman.  People hate us.  We’re even prone to hating ourselves.
I think we should enjoy the few privileges we have.  One of those privileges is that we get to enjoy both passive and penetrative sex.  Please revel in that.  Please enjoy the benefits to being Gay. Seriously.
BTW.  That constantly pooping feeling?  It goes away. Keep practicing.
How do you get to Carnegie Hall?  Practice Practice Practice.
P.S.  How do I feel about barebacking?
Please be safe?  AIDS is still real.  HIV is still a pain in the ass.  It’s not a joke.  It’s your life.  Please be smart?
Don’t. Let. Anyone. Bareback.  You.

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