I'm in love with my son's high school friend

And I told him about my feelings. Now what should I do?

By Cary Tennis
Published February 3, 2005 8:00PM (EST)

Dear Cary,

I am female, about 50, divorced a long time, and parent to two teenagers. The oldest, a son, is a senior in high school. He's old for his grade, though, having gone on an exchange program. He and I had some rough going for awhile with a little physical violence and lots of verbal abuse and arguments. The exchange program gave us a break and things are better now. Also, I no longer try to control him. However, I do push him to stay with friends (usually college friends) when he is unwilling to help around the house, when his stream of visitors greatly disturbs my sleep (we live in a smallish apartment), or otherwise when our relationship is rocky. Lately, he's been parking on a friend's couch quite a bit and so I feel more in control of my surroundings and my life. Basically, my son and I are getting along OK now and I am looking forward to him moving out amicably after graduation.

For the last couple years I've had intense feelings for one of my son's friends, whom I'll call Jesse. He is just 18. My feelings for Jesse started around the time Jesse stood up for me against my son who at the time was being a real jerk. I didn't realize I was developing feelings for Jesse until weeks after the event. One day I just saw him differently, i.e., romantically. Over the last nearly two years my feelings for Jesse have taken deep root. He has matured into a really great young man and I have also had many opportunities to observe his character, brains and personality. Simply put, I now see him as the ideal man, either as son or lover.

My heart is often stung with poignancy and regret that I couldn't have been born into his generation and had a chance to have a romantic relationship with him. Other times I retreat into a very metaphysical state of mind: I think that it is enough that I can love him in a mental way. I also comfort myself by thinking that such pure mental love will more likely survive the ravages of time than sexual love would have. Regardless which spin I put on the feelings, they are pretty one-sided. Jesse likes me a lot (he's said so), but I think that's where it ends. He is aware of my feelings for him because I have stated them. I've never tried to get physical with him and the main manifestations of my feelings include giving gifts, concern re his schooling/college plans, statements of affection (only once anything as direct as a statement of love), fond looks and an eagerness to talk with him when I occasionally see him (not often these days). He has not had a girlfriend before and is now beginning to have one. This is an emotional blow to me even as I know rationally that there is no hope for a romantic relationship with him. I bury these feelings as much as possible so I don't radiate the air of a pervert or loser.

Instant messaging with me a couple months ago, Jesse suggested I actively try to date so as not to think about him so much. This leads to the other part of the puzzle. I want someone to love emotionally and physically but I haven't had a date, or sex, in years. (BTW, I am not overweight or unpleasant to look at. I just don't meet anyone with whom there is mutual interest.) After my conversation with Jesse, I resolved to try to date. But I soon realized what I had inchoately felt: I'm not interested in men around my age or older. I visit mating/dating Web sites and I do not have an iota of attraction, physical or otherwise, for anyone who would be willing to consider a woman anywhere near my age. Also, I hate almost everything about middle age -- the settledness, the mental and physical doughiness that seems to replace the vitality, innocence and cockiness of youth. It's as if the last three years of being around my son's crowd and the high school scene in general has ruined me for people my age. Yeah, high school tends to suck when you're in it, but when meta-experienced through the prism of middle-aged confidence and self-knowledge, youth seems entirely different and superior to the conventionality and sanded edges of middle age. My dating potential is also narrowed by working in a female-majority work environment and by being relatively new to this area where I haven't much put down roots and don't really want to. (I'll leave when my other kid graduates.)

I am by turns really depressed that I am lonely and loveless and that biology and the human condition work against women of a certain age mating, and delightfully happy that I have finally found a good man to love, even if only in a platonic, one-sided way, in the person of Jesse. (FYI, my personal love history pretty much sucks. I hooked up with unfaithful, charismatic people and a couple of alcoholics -- all in all, in retrospect, no one that was near to being right for me.)

Anyhow, please don't suggest counseling. I don't want to be marked with a red P (for pervert or pedophile) by talking about this issue with a professional. I also don't want to be encouraged to join this or that club or organization. It's not me. I also don't want someone to suggest that I visit a man-whore (as one of my male friends suggested). I don't think I could pretend that I was being loved. Also, don't suggest I try to find (via the Web, etc.) one of the handful of younger men who'd date a much older woman. I really think I only warm up to folks I get to know in a natural way.

Jesse is the closest I've come in forever to a good, decent, smart, sweet man who really likes me and has some feelings of concern for me and with whom I feel resonance. Since neither my son (who, like his dad, is charismatic but not particularly honest or appreciative) nor any other man fills this role, I am desperately unwilling to excise Jesse from my heart. The metaphysical platonic spin I put on my feelings saves me from feeling totally deluded, but it also allows great emotional energy to flow to a (one-sided) relationship that probably at most may become a warm, intergenerational friendship. Of course, that could be a good thing in its own way.

The idea of Jesse warms my heart immensely and gives me some happiness when I otherwise would feel lonely and bitter. When I let my love for him suffuse my heart, I don't feel this terrible chip on my shoulder for having wasted my finite years of prime feminine attractiveness on all the wrong people. In that regard, he represents a positive force. Still, he also represents an opportunity cost. As someone who spent decades throwing good money after bad in various lousy relationships, I should learn not to waste my time on things that won't pan out. But this situation feels different since the object of my affection is, for once, a really worthy person. However, he's 30-plus years younger than I am and doesn't see me or need me in the way I see him.

Thank you very much in advance for your thoughts.

Idealist, Pervert or Other? (IPO)

Dear IPO,

Thank you for writing. I do have some thoughts. But I offer them with uncertainty. Usually people ask a question -- my husband is beating me, what should I do? I can't stop drinking, what should I do? Even when a question is too vague, at least it is a question. Your letter is different. There is not a single question in your letter. The only question mark appears in your signature (perhaps unconsciously you want to ask "What is my true identity?").

So I was at first uncertain how and whether to respond. When I did decide to respond, it was because, much as I might want to, I could not turn away from your letter. As an artifact, as a document, it was strangely compelling.

Nonetheless, at the outset I feel I should respond as though you had asked me at least one question: What should I do about this relationship? My answer would be that you should end it. I say that because no matter how you look at it, nothing good can come of this. There will never be a satisfying relationship with this boy. That's not going to happen. All that can come of this, at best, is more strange, muted misery.

That said, I also note that your letter contains a number of preemptive challenges: Don't suggest counseling, don't suggest joining a group, don't suggest finding a male prostitute. It's as though you are asking for help but trying to control the outcome. Sometimes when people attempt to foreclose on certain solutions to their problems, it's because they sense that those very solutions are the ones that are necessary. Sometimes it's because one feels he is utterly unique: The world has never seen a person with problems like mine! The world has never encountered more of a badass than me! It usually turns out that others have been through the same thing and have relevant experiences to relate. So it's useful to keep an open mind and not preclude any potential avenues of discovery.

I don't mean to belabor this, but I have to take it step by step.

So I think to myself, if you haven't asked a direct question, and you've ruled out some of the obvious suggestions I might make, my challenge is to find the implicit question in your narrative -- other than the riddle of your true identity which your signature hints at. So I ask myself, What is at stake here? Is there any potential harm here that might be averted? If so, what can I do in this moment to avert that harm? So the question that develops is: Could this behavior that you describe become harmful at some future date?

People with harmful compulsions often will tell us that they don't know the source of their compulsions, or how, precisely, they arose. One day they just had this terrible compulsion! You say that this feeling arose suddenly without warning: "I didn't realize I was developing feelings for Jesse until weeks after the event. One day I just saw him differently, i.e., romantically." So there is at least the possibility that your attachment to this young man may represent some kind of compulsion. Many people with compulsions also have a moral sensibility. They are basically decent people. If they knew the source of their compulsion and could change it, they would. They are capable of understanding the destructiveness of their behavior, yet they are powerless to stop it.

So let's hypothesize that if one of these perfectly decent people who develops a compulsion had been able to identify in advance the early signs and treat it before it developed into something harmful, that person, being reasonable and compassionate, would have done so, even at some considerable inconvenience to himself. In doing so he might prevent the damage to others and to himself that would ensue if the compulsion were allowed to mature.

Most likely, by submitting himself to some kind of examination, he would simply verify for himself that he was not in any way compulsive or potentially compulsive, and he could move on to other more interesting questions. So wouldn't it be the reasonable, socially responsible thing to go and find out if you are perhaps in danger of developing some harmful compulsion? If not, no harm done. If so, better dealt with than allowed to blossom.

How you find that out would be up to you. Common sense says if you want knowledge, you have to get it from the people who have it, whether they are psychological researchers or therapists or scholars of theology or philosophers.

I'm figuring you'll be able to determine, with a little honest work, that you are not in danger of developing a compulsion. That will probably set your mind at ease. It might also signal a period of self-discovery that will leave you healthier, happier and more accepting of yourself. Assuming you conclude that you are not developing some kind of compulsion, there are many questions that follow, which I would think you would actually find stimulating and challenging: What does the world's store of wisdom have to say about relationships with profound age differences? What does it mean that you, at this point in your life, have found yourself in love with someone so much younger? Wouldn't you want to consider this question as artists and thinkers have considered it over the ages?

In the course of answering your questions about yourself, you may be surprised at the depth of your regret over the choices you made in your youth. You may be surprised at the passion for youth that you still have. Perhaps you can learn to redirect that passion to your own life, and to cultivate your own youthfulness with all the passion that you are now lavishing on this young and unattainable symbol.

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