Advice: Am I leading my friend on?

Mila Kunis and Justin Timberlake in "Friends With Benefits": ridiculously good-looking

Mila Kunis and Justin Timberlake in "Friends With Benefits": ridiculously good-looking (Sony Screen Gems / July 19, 2011)

My friend with benefits told me he has feelings for me and wants to date me. I told him I hadn't thought of him that way and to let me think about it. We continued to be physical for a while, but I came to the decision that I don't want to date. I told him that and we've stopped being physical, but still talk every day. I've told him I'm afraid I'm leading him on and he told me he knows where I stand. He's also told me he still feels the same way and will continue to try. In an ideal world, I wish I could have him as my friend with benefits, but I know that's out of the question. I know I am leading him on, so my question is, what is the right thing to do? I love talking to him all the time and don't want to lose him as my friend. Do I need to give him space though?--What Now?

You’re not leading him on, What Now. He’s leading himself on. But either way, it would definitely benefit your now benefit-less friendship if you made yourself less available to him for a while. How much time and space apart is up to you, but make it a clean break: no texts or calls and, as you’ve already noted, no more playing hide the peach gobbler.

Treat it like a breakup, which it kind of is. You’re changing the rules of your relationship. This is to save the friendship, which can’t keep functioning successfully if one party is carrying a huge torch for the other. Especially if he’s professed he’s going to “keep trying.” (As an aside: Why do we do this to ourselves? Why do we think we can convince people to love us through determination and being hard to get rid of? It’s banana sandwiches!)

You can be friends again with this guy when he can honestly answer that he’ll be happy for you when you start dating or sleeping with somebody else. It is, unfortunately (fortunately?), on you to be the boundary-keeper of this break/change in the relationship with your hopefully-soon-to-be-platonic friend. But remember that the short-term heartache (both his and yours) will be worth it in the long haul, when you can look back as pals and share funny sex stories from boners gone by.

I’ve been sexually active for over 10 years. I've been dating my girlfriend for about two years now and sometimes I can't keep it hard for her. Also it's embarrassing to say but with her I never really ejaculated from the sex. I can come If I'm masturbating but not when we have sex. Have you heard this before?--Mr. X

Of course, I’ve heard this before. It’s the only reason I attend those NRA Women’s Leadership luncheons (though the mini-quiches come in at a close second). It sounds like there could be two reasons why you can’t ejaculate from sex: anxiety or too much of the same masturbation routine. (There’s also a third medical possibility, but you’d have to consult a doctor about that, and I don’t mean WebMD). I’d suggest adapting your jerkin’ routine. Your member may simply be accustomed to the way you touch it, which isn’t easily replicated by a woman. Switch hands, use a condom, loosen your grip -- basically teach it to respond to a different touch and see if that helps. You could also try masturbating until you’re reeeeally close to orgasm and then let her finish you off. The trick is to reprogram your little brain so that it’s receptive to partners other than your trusty hand.

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