by Rudy Cheeks

Dear Dr. Lovemonkey,

I am a 35 year-old professional, divorced female. I have a two-year-old daughter, and a babysitter who I would like to know more intimately. "Jacob," as I call him, is 18 years old and will be leaving for college at the end of this summer. He began sitting regularly for me several months ago and since that time I've grown to appreciate his wit, his intelligence and his "old soul" maturity. I cannot say that I have fallen in love with Jacob. His age and inexperience keep me from seriously thinking of him as a long-term commitment. I do, however, enjoy his company and feel attracted to him. I also feel fairly certain that he is physically attracted to me. There have been a few not-so-subtle hints that this is the case. Ideally, I'd like to have Jacob as my summer lover. I'd like to preserve the friendship element of our interaction and have a little (or a lot) of casual sex with him. I feel like it is a safe bet that he could accept the limitations on our relationship -- he already thinks in such an adult and responsible way. I am also aware, however, that my own desire could be a blind spot for judging him.

My questions to you are threefold: First, I want to know how feasible you think this kind of relationship is. Is it too unreal for me to expect such a no-strings relationship from an 18-year-old? Second of all (and here I really need some coaching), how should I broach the subject with Jacob? Should I try to seduce him (and, if so, how should I go about that?) or should I try to engage him in a conversation? Finally, do you know of any resources (aside from popular fiction) where I could learn more about the nature of older woman/younger man relationships?

-- Ms. Robinson

Dear Ms. Robinson,

Since your nom de plume makes reference to the film The Graduate you may recall that Benjamin's (Dustin Hoffman) tryst with Mrs. Robinson (Anne Bancroft) did not turn out to be an ennobling experience for either of them. Being an "old soul" does not necessarily negate the assumption that Jacob undoubtedly has young, eighteen-year-old hormones. Wise as the doctor may have been at eighteen, I do believe that I would have (in the words of writer-director Nora Ephron, in describing her ex-husband, Carl Bernstein) "fucked a Venetian blind."

Yes, I believe that it is "too unreal" of you to expect anything good to come from poking the babysitter. This may or may not be a "sexual initiation" for young Jacob. If it is, a "no-strings" liaison with an older woman may not be an experience that will serve him well in developing healthy and responsible attitudes and feelings about the role of sexuality in his life. Sex is a powerful thing, especially for a teenager. I seriously doubt if it is a very good thing for him to be dealing with it in a casual manner. He is still developing emotionally and I believe he would experience strong emotions if he were to be involved in a summer fling.

As a responsible adult, I would expect you to know that. Dr. Lovemonkey would only sanction such a thing if you were to go to his parents, explain to them that you would like to engage Jacob in a "learning experience" to help develop his emotional maturity and seek their approval. Somehow, I doubt that this is what you have in mind.

There are certainly different opinions on the mentor/student dynamic in sexual relations. Both Socrates and Allen Ginsberg had a different opinion than Dr. Lovemonkey on this, but I suspect that, as seriously as they took their teaching, they were just horny old guys. I would confine my summer flings to official adults and not play with the fire of young and still developing youth.

Dear Dr. Lovemonkey,

A few weeks ago my lover left me to be with someone else. During our relationship we experimented with all things sexual. I even watched him receive oral sex from a transvestite one night. Now that he's gone, I am trying to figure out how to move on, both emotionally and sexually. I know that time will take care of the pain in my heart, but now I am wondering how to fill the void in my sex life. I have read personal ads and am interested in continuing to experiment -- perhaps with a woman or a couple. I am wondering how safe this is, as I have never been in this position before.

-- Just Curious

Dear Curious,

Probably about as safe as it was with Experimental Boy, which is to say, not very. There are precautions that can and should be taken when engaged in sexual experimentation. I assume that you are familiar with the host of sexually transmittable diseases out there. If not, there are plenty of resources available for getting up to speed and it is your responsibility to check them out if you are intending to be a sexual experimenter. As the old saw goes, you are sleeping with everyone your sexual partner or partners have had sexual relations with, and vice versa.

Apparently your plan is to engage in risky behavior. This is true regardless of how you manage to recruit your sexual partners. Going the personal ads route does tend to ratchet up the risk factor, and the same is true for partners met over the Internet. That's because there is a greater degree of anonymity involved.

Of course, the old fashioned routine of meeting someone, getting to know them well, sharing intimacy and a commitment to each other is not a fail-safe method, but it certainly has many more built in safeguards, emotionally and medically, than your modus operandi. But, then again, you don't seem to be looking for that sort of thing, you're just interested in sex, and that, Just Curious, is a far more dangerous business. There are a number of things you can do for protection, but what you are proposing has nothing to do with being "safe." As a proponent of the ancient school of melding sexual intimacy with human intimacy and commitment, Dr. Lovemonkey is not a big fan of self-indulgent sexual activities. Advising someone on how to act responsibly in an implicitly reckless context is a losing proposition for the doctor.

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