Dateless-Man vs. An Awkward Escape Clause

“Beggars can’t be choosers.” – Proverb

Being a man who is severely inexperienced with romance past a certain age brings with it a lot of interesting dynamics. By interesting, of course, I mean either awkward or terrifying. You have things to keep secret, yet which can’t remain secret should you proceed to resolve them. You have less perspective on this very common fact of life, and find yourself having to dance around conversations or expectations to avoid giving it away. And you also have to combat certain attitudes about sex, love, and dating not only from peers, but society and your own head.

There tend to be two major schools of thought regarding older male virginity. One is to gradually become more fulfilled with your own interests and at least try to make any lovers you have meaningful. After all, a very common complaint about more “experienced” people is some regret that their first time wasn’t with someone they would have liked, or they had a few regrettable sexual encounters for dumb reasons. Men especially are encouraged to treat sex like experience points in an RPG, or think of it like that. A lot of anxiety I and others in my lot feel is the sense that we are not “real men” unless we can assert it through either sex or violence. This is baloney based on sexism, but it persists. Even in circles involving less experienced men talking about their fates or thinking about it themselves.

One attitude which can persist in some places is the sense that an older male virgin simply has unrealistic standards. That all he (universal he) wants is a perfect living doll regardless of his own physical state and anyone less is ignored. That if only he was more willing to “take what he could get”, he’d “get laid” and so on. And there is some truth in this for some; some people do have unrealistic standards. I never thought I did; the sheer volume of women I have found attractive as I went about my daily routine for over 30 years has been too varied to suggest that. But to me it represents a paradox. Desperation is seen as an unattractive trait; yet any older male virgin who isn’t so desperate as to leap upon any and every sexual opportunity, no matter how vile or awkward, “just doesn’t want it bad enough”. Even peers who share this state can occasionally be just as judgmental in this regard than any studly jock.

Which brings me to the subject of this article. Anyone who’s been reading along with the blog for a while may realize I sometimes use lengthy introductions to avoid having to discuss subjects I find awkward. And I may as well type it out before I clarify. The gist of is that my mother has a slightly older friend of hers who has usually made no bones about finding me attractive, and I could probably lose my virginity to her without much effort on my part – if only I was willing to sleep with a woman I don’t feel anything for who is friends with my mother.

An “awkward escape clause” indeed!

I briefly mentioned my mom’s friend before, in “The Last Actual Date”. She was the one who set me up on it (with a much younger co-worker of hers). A lot of backstory is needed. For a long stretch of time, my mother (before she was disabled) worked at an artist’s school and met a lot of wild and wonderful characters there. One of them is a woman I’ll dub “Dee”. They’ve been friends maybe twenty years or more. And like a lot of older women who have been friends over a decade, they have had periods of time where they didn’t talk and hated each other, only to reconcile eventually. Dee is roughly around my mother’s age (call it early 60’s), works as an artist’s model at the school, and is both a little eccentric and very “liberated” in her romantic life. She is also a major fan of Superman. As far as I know she’s never been married nor doesn’t seem to want to marry. Much like my mother did in her youth, her own sexual conquests almost seem to be a hobby. “I like sleeping with young white men,” is something Dee’s said in my presence during dinner. Her current on again/off again boyfriend is a priest who is cheating on his vows with her. She’s also hardly monogamous and, like mom, can sometimes be a bit “risque” when talking about sex. I’ve met her at various times throughout my youth and once I was in college it seemed to get out somehow that she found me attractive.

The last time I saw her was maybe 7 years ago when she, my mother, and I had dinner. It was around either my birthday or Christmas and she gave me a cheap hand-me-down ring as a gift. It was maybe a couple of years after she’d set me up on that blind date with her colleague (which Dee apologized for, which she didn’t have to do). I didn’t talk too much but Dee and mom talked plenty. At the end of the dinner mom seemed to reaffirm the rumor that she “liked me”. I hadn’t noticed; Dee seemed to talk about her usual topics. Her torrid dating life, some of her thoughts on society, happenings about her job, and Superman. At one point I joked about her “having a shrine” to Superman at home and she deadpanned, “How did you know?”

The biggest problem with such a situation with Dee is that I have no genuine feelings for her. We don’t seem to click or have any chemistry in terms of personality. Without describing her looks the best way to put it is that she doesn’t click for me physically. She isn’t ugly but I just feel nothing there. It seems beyond obvious that Dee wouldn’t mind a “booty call” from me, or at least once did. However, I obviously have never taken her up on that or explored it. Least of all because I find it awkward that someone who is my mom’s friend and around her age is into me for a “booty call”.

One of the oddities of being among the romantically inexperienced elder male communities (whether I want to be or not) is that sometimes they (or we) have a knack for being victims of “traditional male culture” while also strictly enforcing it. And I say this with personal experience in how I view myself. After all, a great deal of why I have a poor self image is because I am unable to fit my own criteria for masculinity which is within my own head. The anxiety older male virgins feel is not just coming from society and culture norms, but from their own feelings and enforcement of it. And one of these dynamics is the sense that “a real man” takes any sex he can get (so long as it is among consenting adults, although too many men see that as debatable). If he doesn’t, so goes the theory, then he “doesn’t want it enough” and “deserves” to be a virgin and unloved. Traditional “male theory” is that it shouldn’t matter that I feel no desire emotionally, intellectually, or physically for Dee, nor should any feelings regarding her age or role in my mother’s life exist. I should just capitalize on the opportunity, especially as someone who laments at length about being a virgin. Especially as someone who at least entertained the notion of prostitutes in Vegas or sexual surrogates inside my own mind as a temptation. I could easily imagine at least one of my friends (probably a guy one) encouraging me to put all this aside and try to move forward with this “opportunity”.

One of the many frustrating ironies about my life is that while I haven’t ever been considered attractive to women around my own age who I was into, much older women have always found me attractive. During the last few years of my grandmother’s life I spent a lot of time in various nursing homes and I can’t count how many old ladies blatantly flirted with me. Nothing like poor vision, heavy medication, borderline incarceration and at least a half century (or more) of an age gap to make me a stud, huh? Every man wants to be a “lady-killer”, but with that crowd it could get too literal. Maybe there was a time where men like me were considered attractive, but that time is long past and isn’t coming back. I try not to get nostalgic for an era I never lived through. So add this factor into the situation with Dee and one can see how it can seem complicated when I think about it.

Plus, how would I even go about it? Just call her up and ask her out? Have a ridiculously awkward “date” before the…other stuff? And attempt to go through the physical motions with someone I all but literally have no feelings for? Would grinding through the physical act of sex with a willing person even if it went against what I am comfortable with be better off for me in the long run? Besides, I’ve never talked with Dee bluntly about this sort of thing to begin with. In theory, one of the few “advantageous” (or “less horrible”) parts of being an older male virgin is supposedly getting to have some more choice about one’s “first time”. In real terms, too many people out there were raped or molested or pressured into sex when they weren’t ready, and it is a source of trauma. In other terms, many people tend to regret their first time, usually with someone in their youth who they slept with due to the same reasons why I even fret over this thing with Dee – social pressure and hormones. I’m older and not enslaved to my hormones, and old enough to know better. This doesn’t even get into some ramifications of those around me. While I am sure Dee won’t “attach” to me or see it as anything deep, how would my mother react? She’s an ex-free love hippie herself (a fact which makes my virginity very ironic) who has said she would understand if I did so, but she’s also said that knowing my position of having no intention of doing so. Lord knows it could drive a wedge between mom and one of her longtime friends. I am not a prude and have no issue with a “booty call” or a promiscuous woman (so long as all parties in her life know and accept it), but something seems off about a situation where I have no emotional or physical desire, and all it would be is a physical transaction I feel I am doing for “my own good”. Literally all I would get out of it is finally being able to not be a virgin anymore. A sexual surrogate is part of genuine sexual therapy, and in theory a Vegas prostitute would be someone I could choose specifically because there would at least be physical desire there. And those are options I have rejected outright.

Is it wrong to want to have a first sexual encounter where I at least have some genuine feelings for someone else on an intellectual and/or physical basis? Even for just a short period of time? I don’t mind being the object of someone else’s fantasy or booty call, it just feels off to just go into it for the act itself, and for there to be no kind of passion or genuine energy in it. But perhaps I am wrong. Perhaps I should jump at this chance to finally shed my shame in a perfectly legal and consenting way. Most people’s first time is hardly perfect and mine likely won’t be either (especially since I am sure I will be physically underwhelming for the woman and she will either be disappointed or disgusted). But something about it feels off, feels wrong.

Deep in my heart maybe I know that the sheer act of sex won’t “fix” or alone improve upon many of my faults and problems. And if it won’t, maybe it isn’t worth it to lose it in a deeply uncomfortable situation just because it maybe presents itself. Unfortunately, the alternative is more lonely nights, more feelings of woeful inadequacy, and more lost months and years in a pit of despair over this. You can’t put a value on integrity, but it won’t keep you warm at night either. I am tired of being a freak, a comedian’s punchline, a facade of a man. Yet I am apparently not so tired of it that I am willing to take advantage of an old woman’s fetish with a wince just to check a box off a list. It is who I am. And that is…the Dateless-Man.