Archive for the ‘advice’ Category

The red sex

Dear Cary Blackshaw,
I’m a hardcore liberal democrat. I know a person who is a hard core conservative republican and we have nothing in common. However, we have hooked up many times and it is the best sex of my life. Why is it that I’m having the hottest, most mind blowing, toe curling sex ever with someone I can’t stand otherwise? Do republicans just secretly wish to be dominated?
Blue in Arizona

Hi there Blue,

First of all, so sorry for being MIA. Secondly, I must talk politics with you. I’m sure you’ve noticed with the latest debt talks and all how Republicans can be. They aren’t lovey dovey. They are in your face crazy stubborn borderline fools. Which, as a liberal, is the opposite of you.  And as humans, we’re attracted to these individuals who are our polar opposites. I’m sure you’ve seen it in TV shows where the two diametrically opposed forces are also bed-mates (I’m looking at you Jessie and Slater from Saved by the Bell!). Is it sustainable? Probably not because you do need more of a connection. But in the meantime I say go for it!

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Buddy Crush

Dear Cary Blackshaw,

So, I’m in love with my best friend.  I know this is a common occurrence among gay friends, so hopefully you have some ready-made advice.  At first, I wasn’t interested in him romantically, but as the years have passed and I’ve realized how amazing he is, I find myself pining away for him.  I don’t have any other close friends, and I love how he makes me feel loved, appreciated, and worthy of his time.  He is the only person in the world with whom I truly feel 100% comfortable just being myself.  Based on some of his actions, I have my suspicions that he may feel the same towards me, or at least has some feelings for me.  I honestly feel we’re perfect for each other, but I’m scared of approaching the issue with him because if he isn’t of the same mindset, I don’t want to lose the best friend I’ve ever had in my life.  We have so much fun together and he means the world to me.  It will sound silly, but I really don’t think I’ll ever find anyone else who makes me feel the way he does.
What should I do?

In Love With My Best Friend

Hi In Love,

Your situation reminds me of that Whitney Houston/Stevie wonder song “We didn’t know.” If you don’t know it, I highly recommend you look it up; it’s from her I’m your baby tonight album (so pre-crack). But basically it’s about two friends who didn’t realize they loved one another. And based on what you’re telling me, it’s quite possible the feeling’s mutual. However, there is that possibility that he’s completely  oblivious to it all (some people really can’t see what’s staring in front of them), but again, I’m thinking that’s probably not the case.

As the old saying goes, “a drunk man’s words are a sober man’s thoughts” That’s right, get him drunk. Not wasted, just pretty tipsy so the tongue starts spewing things. And do it somewhere fairly public, like at a wine bar or a cozy restaurant. I recommend red wine (my favorite is Port and yes it’s a dessert wine but I don’t care, it’s delicious). Just talk and see where it leads. By having it in a public setting, it means that if something said piques your interest, you won’t be tempted to jump his bones right then and there, and we can’t have that. Just take it slow, but above all, be yourself. Of course that’s a double bind; how can you tell someone to be themselves when the act of being yourself is just that? But we won’t get Zen on this. Just do you.

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You Still Remember Me?

Hi Micahceous,

So I was out at a bar the other night and this guy walks up to me and asks if I am who he thinks I am. I respond “yes, why?” and he proceeds to tell me that he chatted with me years ago on connexion, remembers where I went to college, where I was from originally, bla bla bla. It must be like 4 years ago that i chat with him. The guy is … cute but definitely overweight. Seems nice enough but whatever. So then he e-mails me that night with his phone number and that I should call him so I just wrote back “thanks.” He comes back with “what’s your number?” I don’t want to be rude or anything but I don’t really want to hang out with him.It wasn’t like we had any meaningful conversation. So what do you think the next step should be?


Hi there F,

You left quite a mark didn’t you? First of all, weird. Ever stalker should know that you should feign dumb when admitting how much information about your stalkee you have stored in your head. Otherwise it’s clear you’re a stalker! I’m not saying it’s not okay to remember someone some years after the fact, I think that’s normal. It’s one thing to say “I met you at a conference x years ago” versus “you drank three vodka-rum concoctions at X Bar after the seminar session on how to target youth in advertising held by Buzz Killington.”

You have two options: ignore him or be honest and say you’re not interested. I’d go with the latter cause based on his history, the kid can’t take a hint. Plus really, sometimes it’s better to be straightforward. Be honest. Say something like “hey it was nice meeting you. have a good time, take care.” by saying “goodbye” to the kid you’re kinda blowing him off but not entirely.

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3’s a Crowd

July 30, 2010 1 comment

So, I need help!

I have been dating this guy for over 10 months now and the chemistry is  great and we found ourselves deeply in love early into our time  together. We both love each other dearly, deeply, immensely… But he  wants our relationship to be open. He was upfront about this so it’s not  like he twisted my arm. I have never been in one but because I really  liked him (in the beginning) I thought I’d be open about and see if it  something that I could do. He wanted this status because he doesn’t like  to feel “boxed in” or “tied to” just one person. He claims that  encounters would just be a fuck – nothing more. He is on several  websites but hasn’t had much luck. He introduced me to the idea of  3somes/4somes, swapping.. and again, I wanted to be open so i tried it.  Not my thing. To cut to the chase, I am at the point where I fully  realizing that this behavior is not for me and he has clearly said he  will not be exclusive with me. He argues that he loves me and that doing  these things won’t change
things. He feels that I am being selfish and greedy for wanting more than what he can offer.
What is your take on this?


Dear Trinity,

Open relationships aren’t for everyone. And some argue that it dilutes any trust or bonds two people share. It’s really between the couple in my opinion and if there’s a break in communication then it needs to be stressed what you want. Don’t stay in a situation that will make you unhappy. And if a guy is telling you he doesn’t want to be tied down to one woman, then he doesn’t want a relationship. He just wants to fuck around. And there’s nothing wrong with that but you and him should be honest about what you both want. Don’t be afraid to walk away. I think he’s being greedy and selfish for not respecting your position. And if he’s unwilling to bend, then he’s immature and not worth your time.

If you really wanna keep him, tell him that it can be open but under your rules. This can include only having 3somes or more if both of you are present (as opposed to him being able to sleep with anyone he pleases) or you can do the coup de grace and tell him your needs aren’t met and that you want a MMF 3some. In addition, tell him that it’d really get you off if you saw him take it up the ass from another guy. This could drive a guy to be so stubborn as to end this whole open relationship mumbo jumbo. But be aware that this could backfire. If he says he’s more than willing, or is even excited about that prospect, congratulations. You’re dating a gay man.

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Happy some of the time

July 30, 2010 2 comments

Hello Micahceous!

Here is the deal. I found a REALLY fantastic guy. He cooks and cleans and he treats me really great! Now here is the problem…….I’m not happy about 40% of the time, but who is happy all the time, right?!?!?!, I’m not sure what it is. We moved in together about 9 months ago and he more than carries his weight with expenses and household duties, I’m attracted to him and genuinely feel as though I love him. Something is missing though. I’m a communicater and he isn’t so I thought that may be it but I’m not sure. I am tired of having the communication talk though, but is that enough to break up with someone?

We don’t fuss, fight or even argue. We have good sex and I’m attracted to him. We actually honestly LOVE each other but is that enough? Doesn’t it take more? I have a friend who says if you ask any divorced couple why they got married they will say “because we were in LOVE”….. We are always very polite, pleasant and respectful towards each other and that makes me think I’m crazy to be thinking about leaving him. Who leaves a set up like that, right?!?!?!?!

I also feel like I would be pulling the rug from under him if I left him. He has come out of the closet to his family during our time together. He didn’t come out for me but it was something that was a point of contention for us early on (me being out and him not). I told him to do it for him and not for me and to do it when he was ready. He came out a few months ago to them and although they have seen each other they haven’t really talked about it and I feel like he needs me. I wonder about where he would go, what would he do. In our time together my friends have sort of taken him in as well because his friends are kind of non-existent (he has friends but they are not as quick to assist in a jam like my friends are). I find myself in two different relationships: The one he sees and I portray and then the one going on in my head……..On one hand I am the good boyfriend, kissing him when I come and go and saying the “I love you’s” where appropriate but in my head I sometimes wonder
how I can leave and not hurt him. Then after thinking those thoughts I wonder “is it me?” why do you want to leave a seemingly perfect relationship. He loves you, you love him, he has come out the closet, he takes fantastic care of you etc…..

Help! going crazy over here!!!

-Almost Perfect

Dear Almost Perfect,

Being unhappy 40% of the time is a lot of time. Think of it this way: if planes crashed 40% of the time you wouldn’t ride them, right? Oh and for the record, I’m happy a good 99% of the time (that 1% being when I find out I should’ve waited a week before buying that shirt since it went on sale).

It sounds like you have a large sense of guilt and feel like it’s your duty for him to be dependent on you. And that’s simply not the case. You do not have that sort of responsibility and in the end it’s up to the individual to make themselves happy. It’s entirely possible that you’re not ready for this “seemingly perfect” relationship. Things can sound great on paper but not be for you. It happens. So don’t think you have to stay because it’s seems like a perfect relationship, because obviously with you being unhappy a whopping 40% of the time, it’s not perfect.

In the end, only you can make yourself happy. Life’s too short to be unhappy 40% of the time. If you genuinely want to leave him, then you should. And it doesn’t have to be a vindictive move. You can still be there for him but in a different role. He’ll hurt but he’s not a newborn baby. He’s gotten this far in life, surely he can keep going. And you still care about the guy so I don’t see why you can’t still be an active part of his life, just not in the romantic role. You’ll make the right move and there may be tears and awkwardness at first, but in the end you’ll both be happy. You can be happy a lot more than 60% of the time and he can find someone who is happy full-time too. Win-win. Break it off. Just don’t do it over text.

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Just Friends?


I recently ditched my long-distance, on-again-off-again lover for a more  compatible and more convenient relationship in the same city, but he  still wants to maintain a friendship even though I know he still has  feelings for me.  Can ex-lovers be just friends?


Hi Hall,

I assume a friendship would be limited to instant messaging and seeing pics of your tongue down your new beau on facebook. Before we delve into this further, what makes you so sure your ex is still into you? Unless your ex has told you repeatedly they want to get back together, don’t assume. Do you assume it’s because you did the breaking up and they want to remain friends? Your ex may just want to stay friends cause he semi-enjoys your ramblings and he wants a couch to sleep on and a place to slide his member into when he’s visiting your city. He may not be seeking anything other than that. If he is still into you, then you need to ask yourself what you want. Do you want to be able to call him the minute you and your new lover have a fight to dangle a carrot in front of his face?  Is there a secret desire on your part to get back together? This brings me to my next point: Are you over your ex? You pose that your ex isn’t over you but it could very well be the other way around. If not, then maybe you should get out of the convenient relationship you’re in now so you can stop and think; its okay to sleep alone. If you’re over him and don’t have a desire to get back together, then certainly you and your ex can arrange a way to be just friends. Ask yourself this: “If my ex were to live in the same city as me, would I get out of my relationship to be with him?” If the answer’s yes, then you and your ex can’t be “just friends.” You’ll still have that desire and would need to be honest with yourself about the best course of action.

So can ex-lovers be just friends? Yes. But it requires all parties to be honest about what they want and what they expect.

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Long distance woes

July 23, 2010 1 comment


So, about a few weeks ago, I spent two weekends together with a friend, who at the time was on the fence with his estranged boyfriend. One thing led to the other and we were having a wild, romantic, sexy time back at his place in SF. Seeing that he was always on the fence with his boyfriend to begin with, he simply decided to call it quits on the strength of our sexy, wild time. At the moment, he is working in China for the next three months and I am in South America. In any case, we won´t see each other until at least the start of the fall. We´ve been emailing and Skyping ever since our time together. The great thing is that we have this distance between us to keep a few things in check: I am not completely a rebound, though by nature of our hookup, I am a source of comfort (HE broke it off with his bf, so I am not sure whether he needs comfort). If I am looking to develop anything with this guy, is it REALLY going to depend on the degree of communication between each other until
we meet again? Even then, do you think it´s worth trying to keep in touch? Should I voice these concerns (i.e I am NOT your source of comfort, don´t use me as a replacement for your pain, you need to heal on your own). I mean, I really like this guy, and I assume he feels the same way. Though, I also feel that all the communication we´ve had since our encounter is a bit too much at this stage.  I feel that communicating for the sake of “keeping the dream alive” isn’t necessary, when we already know that we do in fact…like each other. I’d prefer if we just keep the emails, Skyping to a mininum, because I am going a bit crazy thinking about how he is doing all the time, what he’s feeling, etc, etc. I don’t need this, but maybe he does. He was with his boyfriend for two years, and now it’s over. What am I to him?It might not be very clear in the midst of all the cuteness and comfort for me, but what do you think? We both definitely can’t wait until the day we have the space and
time to have a great time together. I just don’t believe in long distance relationships (i.e. they seem to prolong what would otherwise die much earlier were two people to actually see each other day in, day out…which is also a concern I have about the nature of emails, Skype. They keep the dream alive, but I also feel that they retain romantic, wild, obsessive compulsive notions that would otherwise DIE a quicker death were two people to actually see each other day in, day out). Anyway, just a few thoughts! Should I voice these concerns?


Hi Anthony,

Oh the long distance relationship. I did that once and it fell apart. You are completely right in your feelings in a long distance relationship. Plus, it sounds like this guy is really infatuated with you. And that’s a normal feeling to have with someone you like, but like I’ve experienced and seen so many times before, the faster you fall in love, the faster you fall out of love.  You should express you want to slowdown. By not telling him why you’re being distant it could just make things awkward or more painful. Tell him you want space. Tell him you want him to go out and get laid and not wait by the webcam for you.

I think for him, you are a comfort, but not in a way you may think. He’s looking to fill a void and you fill that dark hole for him. Luckily, you’re not balls deep it seems. So I’d suggest pulling out slowly and just taking it easy with him. Just as he may be over-infatuated with you, he could easily fall out of this infatuation and hurt you in the process (like, saying he’s met someone else and breaks up with you via text message because he’s too “busy” to tell you, but I digress). You two are already some 3,000+ miles apart. Take the next step to distance yourselves emotionally, but don’t be mean about it. And after all, it’ll give you two a chance to really know one another on a friend-only level and when you’re back in the same spot you two can decide for yourself where you want to go next.

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