Sasha: Dating impossible men, planning a foursome and finding an orgasm

Please chip in to support more articles like this. Support for as little as $5 per month!

Dear Sasha,

I'm in love with impossible people. I always find myself chasing the people who aren't interested. I've missed a lot of good relationships and hurt a lot of really good people because of this.

I had a girlfriend who was really loving to me, but I lost interest and started obsessing over a guy who was clearly unavailable. It destroyed her, not only because I wanted to be with a man (how could she compete with that?), but also because I started to be a real bitch to her. Nothing she did was ever good enough, and eventually I dumped her. I really broke her heart.

And here I am, single and still chasing after the difficult ones. As soon as they're interested I lose interest, but mostly they just stay dysfunctional and uninterested, or they push and pull. And I keep on chasing.

I can't tell you how much of my day's energy is spent grabbing onto these slippery ideals, but it's a lot. I don't know how to change it. I'm aroused by the wanting. I guess I need tension in my life. Is there any way I can change and be healthier?


Maria, all people are impossible. Whether it's because they are unattainable, overly attainable, clingy, distant, loving or spiteful, they are just fucking impossible. And that includes you, my dear. Intimate life with other human beings is a never-ending compromise smattered with rationalizations and dashed dreams.

As Woody Allen says in his film Love and Death, To love is to suffer. To avoid suffering, one must not love. But, then one suffers from not loving. Therefore, to love is to suffer, not to love is to suffer, to suffer is to suffer. To be happy is to love, to be happy, then, is to suffer, but suffering makes one unhappy. Therefore, to be unhappy one must love, or love to suffer, or suffer from too much happiness.

What does all this exhausting double talk mean? This is how I see it: the way we choose to love is often directly related to the kind of suffering we can handle. We construct different paradigms of loving to accommodate our limits of suffering, not the other way around. For you, boredom is a brand of suffering you cannot handle. And sister, I am there with you. Come on over, let's watch some Bette Davis films.

Dear Sasha,

I am a young woman in search of information. My friend and I have decided to organize a foursome party, and we've each invited our own close friend. So in all we are two men, two ladies. We wanted to research some positions beforehand so that the action has more flow and we're not sitting there together trying to think of what to do next.

We did some googling but didn't find many good foursome positions. A lot had two couples simply mirroring each other. We want everyone involved in the action. We're aiming for a group activity rather than a voyeur party. Can you suggest any good resources that give suggestions on foursome positions and play?

Foursome Party Planner

Listen, babe, I don't know if you've ever had group sex before, but I can assure you that planning your moves in advance is kind of like getting Merce Cunningham to choreograph a mosh pit.

I wouldn't get too fixated on positions and routines. Sure, you say you don't want a voyeur party, but I think when two people are having sex three inches from your face you might just change your mind a little bit, because that is some powerful shit.

Just make sure you have plenty of lube, condoms, gloves and dams. Trust me, the moves will take care of themselves.

Dear Sasha,

I'm 24 and I've never had an orgasm. I've had my fair share of very awesome sex, so that's not the problem, and I've come close a few times (I think -- my whole body starting to burn up). I generally don't masturbate, and when I do I hardly get wet or turned on, even if I use a vibrator (a Butterfly), lube and porn. It just doesn't compare to being with someone.

The odd thing, though, is that three years ago I started to have wet dreams, so I actually do know what it's supposed to feel like (contractions and so on). The dreams themselves are becoming less and less sexual, and I'm more and more removed from what's happening. For example, the last two or three times I had these dreams I wasn't even touching myself, I was just lying or sitting there, and nothing else was happening.

Sometimes I think the problem is more psychological than anything else. At this point I find it embarrassing and I'm almost afraid to come, like a vein behind my eye will burst or that it'll hurt. Sometimes I'll have mild panic attacks and cry uncontrollably for five to 20 minutes.

I just don't know what to do. Are there any workshops or books you can direct me to? I read For Yourself by Lonnie Barbach, which was only somewhat helpful.

I generally know what I like and really do enjoy sex, and this is the one thing that's bugging me most about my sex life. It's something I'd rather keep to myself, but it inevitably comes up with new partners, and I'm tired of it.

At Wit's End

Isn't it amazing that you say the problem is psychological and yet it is your brain alone that is providing you with the only orgasms you're having? As I often ask, ever get that feeling that your brain is smart but you're not? Your brain, when it's not being oppressed by your fear of being vulnerable, is telling you, Come on, Wit's! Let go and have some fun!

So how are you going to do that while you're awake? I think you've got to let go of this ambivalence you have for masturbation -- the fact that you even compare it to sex says you're holding it, and yourself for doing it, in contempt. Masturbation is one of the best ways of learning to let go.

Believe it or not, this couldn't be more normal. The terror we all feel at being exposed stops us from doing many pleasurable things. We feel weak for wanting these things, yet so desperately attracted to them that they give us panic attacks. You need to first accept that pleasure is your ally, not your enemy.

Ask Sasha: [email protected]

Independent rukus-raising news site seeks new friends (at $5/month) for support network. rabble will always be there for you, looks pretty good and has a winning personality.  Loves new friends and will shower them each with a free independent print magazine subscription.  Contact at  No photo required.

Related Items

Thank you for reading this story…

More people are reading than ever and unlike many news organizations, we have never put up a paywall – at rabble we’ve always believed in making our reporting and analysis free to all, while striving to make it sustainable as well. Media isn’t free to produce. rabble’s total budget is likely less than what big corporate media spend on photocopying (we kid you not!) and we do not have any major foundation, sponsor or angel investor. Our main supporters are people and organizations -- like you. This is why we need your help. You are what keep us sustainable. has staked its existence on you. We live or die on community support -- your support! We get hundreds of thousands of visitors and we believe in them. We believe in you. We believe people will put in what they can for the greater good. We call that sustainable.

So what is the easy answer for us? Depend on a community of visitors who care passionately about media that amplifies the voices of people struggling for change and justice. It really is that simple. When the people who visit rabble care enough to contribute a bit then it works for everyone.

And so we’re asking you if you could make a donation, right now, to help us carry forward on our mission. Make a donation today.


We welcome your comments! embraces a pro-human rights, pro-feminist, anti-racist, queer-positive, anti-imperialist and pro-labour stance, and encourages discussions which develop progressive thought. Our full comment policy can be found here. Learn more about Disqus on and your privacy here. Please keep in mind:


  • Tell the truth and avoid rumours.
  • Add context and background.
  • Report typos and logical fallacies.
  • Be respectful.
  • Respect copyright - link to articles.
  • Stay focused. Bring in-depth commentary to our discussion forum, babble.


  • Use oppressive/offensive language.
  • Libel or defame.
  • Bully or troll.
  • Post spam.
  • Engage trolls. Flag suspect activity instead.