Dear Josey,
I’m a 22 and ever since my girlfriend and I broke up two years ago, I’ve felt “dead” inside. I’ve recently met someone I connected with emotionally, but he’s a guy. I don’t think I’m bothered by the “gay” aspect of my attraction as I’ve been attracted to both sexes for as long as I can remember. He’s an “out” bisexual and has let me know that he thinks I’m cute. He knows I’m “confused” and have never done anything sexual with a guy, which is why I think he hasn’t made any moves. Part of me wants to walk up and kiss him but something is holding me back and I wish I knew what. Any advice?
-He Moves Me But I Can’t Make a Move

Dear Moves,
I may be way “off” here, but I’m pretty sure the fact that you’ve felt “dead” emotionally for the last two years and have never acted on your “gay” feelings towards men might explain why it’s a little tough to simply walk up to him and plant a big wet one on him.
But he sounds like a decent guy who’s conscientious about your feelings, so there’s no reason you shouldn’t be able to talk to him about this. Tell him you’re attracted to him but nervous about it because you’ve never been with a guy. If he admits the attraction is mutual, take it from there. It’s really not more complicated than that.
Perhaps what is complicating things more for you, and what is more likely the reason for your letter, is that your first emotional connection after breaking up with a woman is with a guy. You say you “don’t think” the “gay” aspect of your attraction is a problem, but that tells me you’re not entirely comfortable with the idea. Maybe you’re worried that your last experience with a woman somehow turned you “gay” and that you’ll never be able to have feelings for a woman again.
I suppose an experience with one sex can be so bad it makes you want to give up on a gender and try playing for the other team, but I’m pretty sure one bad relationship won’t “turn you gay.” It’s quite possible that, like your buddy, you’re bisexual. The fact that you’ve been “attracted to both sexes for as long as you can remember” is a pretty good clue. Or you may simply be attracted to this one guy. Who knows, really? And who cares? The best way to figure out what works for us when it comes to relationships is through having them. So rather than worry about “why,” be thankful that you aren’t completely “dead” inside and start living.

Dear Josey,
I’m almost 20 and have never had an orgasm. I’ve been fooling around since I was 17 and having sex with a steady partner for a year. It’s good but I just can’t fucking come.
I’ve been eaten out for 45 minutes, and still nothing. I’ve tried Kegels (as I write this, I am clenching and releasing the muscles in my vagina), but I don’t even know how that’s supposed to help. I have psoriasis, a skin disease related to stress, and I can’t de-stress by coming! I have migraines, and apparently orgasms make these go away too. I’ve never used a dildo or a vibrator, and maybe that’s the solution, but I’d like to come because of my man, not a toy.
I know you’ll probably start your response with “you have to know your body” but I think I do, and still, nothing. I’ve heard of “anorgasmie.” Could this be my problem?
-Orgasm Not Forthcoming

Dear Orgasm,
You’re right — I would say you do have to know your body, but since you say you’ve got that down, let me address your frustration.
First of all, you’re far from alone. Lots of women, including yours truly, take forever to come from their partner. Unless I offer some kind of manual or mechanical assistance, lockjaw or carpal tunnel are serious job hazards around my bits. But it’s not a less legitimate orgasm if you bring in backup.
And while it’s true that orgasms can release stress and even headaches (though, in some cases, it can also cause them), I’m not sure that you achieving orgasm is suddenly going to make you psoriasis- and migraine-free. As for Kegels, they’ll keep your muscles down there tight, possibly increasing your chances of stronger orgasms once you do get there. And since you know my “you have to know your body line,” you probably don’t need my “the more you focus on the problem, the less chance it’s likely to happen” speech.
But I’ll risk sounding like a broken record. It’s the same principle behind why you never meet someone when you’re really trying. It happens when you’re not thinking about it and least expect it. So definitely lay off yourself a little. And get past your “I must come by man, not machine,” barrier. A vibrator will probably get you off. Try it on your own so you can be totally un-self-conscious and free to let go. Once you know you’re not broke, you might be more confident leaving things in your man’s hands. Just like a guy with erectile problems might need a little blue pill to restore his confidence before he’s able to fly the trapeze without the safety net.
As for whether you have anorgasmie, seeing as it’s just really a fancy French name for “I can’t fucking come,” then I guess, yes. But it’s not like you can take a pill to cure it. Same advice applies.