Dear Margot,

My girlfriend and I have been dating for three months. We had sex on the second date and pretty soon I realized she can’t orgasm without a vibrator. I get off on pleasing a girl with my hands or mouth and I’ve never had any trouble before. How can I make it happen with her or is it even possible? I’ve tried everything I can think of and I’ve told over and over her how I feel.

– Left out in NYC

Dear Left Out,

That’s exactly what you’re going to be if you don’t stop complaining. Your girlfriend gets into bed with you, has an orgasm, and actually still speaks to you after you tell her how unhappy you are with the WAY she comes. Jeez, you must be really good-looking or have a hell of a great job ’cause it ain’t your personality that’s keeping her there!

But since you seem so painfully jealous of your girlfriend’s mechanical boyfriend…there are some things you can do to help her orgasm with another human being.

I consulted sex therapist to the stars, Dr. Stephen C. Josephson. He suggested a technique called masturbatory reconditioning, otherwise known as the ole bait and switch. Here’s how it works: First you bring her to orgasm her preferred way – with a vibrator. Next time, you bring her close to orgasm with her vibrator, like right on the cusp, but then you take it away and bring her off with your hand. The time after that you bring her close to orgasm again with the tool, but not as close as before, and you use your hand? Get it? Each time you do it, you remove the vibrator a second or two sooner. Pretty soon she’ll associate your fingers, or whatever, with orgasm! It might be a one step forward, two steps back deal, but she’ll get there! And while you’re at it try and mimic the type of motion that the vibrator makes. It’s quite different from a hand, but it is possible to do.

Remember that the vibrator is very stimulating, much more so than a hand or mouth, so when you attempt to take it away make sure there is lots of other stimulation in the room. Think porn, literature, other people, whatever – just make it a 360 experience.

Oh and one more thing: Carefully think it over before you begin. There’s going to be a lot more work for you once the mechanical rabbit is out of the hole.

Dear Margot,

I saw my friend’s boyfriend kissing another girl in a bar, which shall remain un-named. I could tell he was really drunk, he could barely stand up, but still, should I tell her? 

– Blinded in Bushwick

Dear Blinded,

I’d lose my tongue too if I were you. In other words I would probably not jump in right away. If there are problems in your friend’s relationship they will show up all by their little selves, with no help from you whatsoever. Who knows, they may have an agreement, an open relationship, or they may simply not be that serious. You didn’t say whether or not this was a close friend of yours or how long the relationship between the two of them has been going on. I’m guessing that she is not that close to you or you would have called her a close friend, a good friend or best friend.

Are you sure it wasn’t you in that bar? My gut instinct is telling me that you have some unspoken reasons of your own for wanting to inform this girl.

ON THE OTHER HAND: If she is your best or close friend then ignore all of the above and tell her. If you don’t it may damage your friendship, as she won’t trust you to be honest. Sit down with her, don’t do it on the phone or via email, and be very supportive. Be quick and to the point, don’t drag it out, and tell her how sorry you are but that you had to tell her because she is your friend and you want her to trust you in the future.

And you know what they say about shooting the messenger. Next time, take a picture. That way the bad news will come out of your phone and not your mouth.

Please send your questions to margot.berwinATgmail.com I’d love to hear from you!