never married, over forty, a little bitter

Category: dating

the uncompromising

I know this is what I’m looking for and hope it’s true that most men want this as well:

What do we know about what young men are looking for in those committed relationships?

What most guys seek, and this seems to be regardless of sexual orientation or age, they’re looking for people whose company they enjoy. People who appreciate them for who they are. We know that a couple tends to be similar in age. More often than not folks match on ethnicity, political orientation and religiosity. The thing that ultimate grounds it are personality match, similar sense of humor, similar tastes in music, TV and movies, similar activities, because you want to be able to do things with your sweetie and you want someone who gets you.

It seems to me that to not have these commonalities in a relationship would spell unhappiness, but perhaps people build families with incompatible partners and look for social fulfillment elsewhere.

In this sense, yes I am “picky” and only get pickier as I get older. Yet so many other things have less importance now. For example, since children are off the table, a man’s provider role is less important, and, in fact, if he were unusually wealthy it would make me uneasy, as I would worry about a power imbalance.

I have dated outside of my ethnic group, but I have always been attracted to men closest to me in age (within five years). Now that I’m getting to the age where I can’t have children, I’d feel guilty dating a younger man if he were at all on the fence about having kids. Having grieved my own lost opportunity, I wouldn’t want to be the cause of that same grief in someone else’s life. On the other hand, I was recently flirted with by a man 10-12 years older than me, and to be honest, I feel slightly uneasy about the age difference, although I know that it’s not uncommon.

I have been in relationships in which we “got” each other, and now it’s hard to go back.

dudes on dating

Two male comics discuss dating and the pressure to get married here:

I have a friend who had been divorced when she started dating again and she looked for (and found) a man who had also been divorced. To her being divorced means that you’ve been through a trial by fire and would know better next time how to make a marriage work.

I’m the opposite. I’m very attracted to that rare species of man who is over forty and has never been married or had kids. It’s a factor of similar lifestyles. If he’s sane and smart and sensitive… ooh la la.

I’m unfamiliar with the other comic but am very surprised that someone like Neal Brennan would use online dating. Maybe guys have it harder than I thought. I’m tempted to assume it’s because they are searching for someone young and extraordinarily good-looking, but it sounds like they just want to find that good match.


The forties and fifties seem to be a common time for people to surrender to their inner introvert:

In my old age (I’m 55) I am just plain happy at home with my husband and son and my horses and other critters and my garden. Doesn’t matter if I’m riding or doing chores, I can fill hours messing with the horses and/or wandering around the garden observing what’s in bloom (in the spring) or ready to be harvested (summer and fall). Truthfully I can fill happy hours watching the spring breeze toss the treetops on the ridges, or watching the goldfish dart around the pond, or the quail pecking in the riding ring, or the lizards catching bugs. I could seriously go on all day listing tons of small events here on my mini-ranch that happily engross me. I like to write, so often I write about these things. I like to take photos…and sometimes I post them here and on facebook. And I like to sit on the porch with a cup of tea in the early morning and a margarita in the evening watching the light change. I am never bored.

Thank god for aging. It wasn’t until I got into my 40s that I began surrendering to the hand I’d been dealt, which involved a long and arduous process of struggling, in earnest, with who I really was. And I’ve come quite a distance. Many years of solitude and introspection have enabled me to get out of my own way. My character has finally begun to take shape and find expression. And I am far more interested in living my own life than anyone else’s, even with all its uncertainty. For the first time in my life, I have found liberation in not knowing. I’m going to be 50 in June, and I’m very, very excited.


I have become someone I never thought I would be and frankly, spent much of my life fighting: a deeply sensitive, unconventional outsider who needs substantial alone time in order to assimilate, integrate and refuel.

That makes finding love extraordinarily difficult. I have spent the vast majority of my adult life on my own, outside the bounds of any conventional relationship. Couples who have found happiness in spending most of their days together are foreign to me; I cannot imagine living that kind of life.


One is never in a good frame of mind to choose a partner rationally when remaining single is unbearable. We have to be utterly at peace with the prospect of many years of solitude in order to have any chance of forming a good relationship. Or we’ll love no longer being single rather more than we love the partner who spared us being so.

Unfortunately, after a certain age, society makes singlehood dangerously unpleasant. Communal life starts to wither, couples are too threatened by the independence of the single to invite them around very often, one starts to feel a freak when going to the cinema alone. Sex is hard to come by as well. For all the new gadgets and supposed freedoms of modernity, it can be very hard to get laid – and expecting to do so regularly with new people is bound to end in disappointment after 30.

Far better to rearrange society so that it resembles a university or a kibbutz – with communal eating, shared facilities, constant parties and free sexual mingling… That way, anyone who did decide marriage was for them would be sure they were doing it for the positives of coupledom rather than as an escape from the negatives of singlehood.

When sex was only available within marriage, people recognised that this led people to marry for the wrong reasons: to obtain something that was artificially restricted in society as a whole. People are free to make much better choices about who they marry now they’re not simply responding to a desperate desire for sex.

But we retain shortages in other areas. When company is only properly available in couples, people will pair up just to spare themselves loneliness. It’s time to liberate ‘companionship’ from the shackles of coupledom, and make it as widely and as easily available as sexual liberators wanted sex to be.

the hermitage

I haven’t been a complete hermit lately but I’m still at the stage where spending time alone feels like a treat. The women I have hung out with recently are distracted by burgeoning romantic relationships or actively searching for them; our time together is oriented toward those conversations and pursuits. I don’t blame them for this, but I’ve got other things on my mind these days. In lieu of people to discuss them with, I prefer to spend time alone, roaming around my own head.

Although I’ve always liked having a social life I’ve come to accept, especially as I get older, that I’m a pretty big introvert. If I do end up with a partner, it will probably be a fellow introvert. I liked this blog post:

The older I get the more I like being on my own. This is not a bad thing as I spend the vast majority of my time actually alone. I work from home and I live alone. I am single. I’m an introvert and find large groups of people exhausting (one-on-one I love). I’m not particularly shy, and can be downright gregarious in the right situation, but on the whole, I prefer my own company.

the leftovers

There are a couple of men who have stayed in contact with me over the past few years of my work/life ordeals. For a variety of reasons, including some enormous logistical ones, I’m not interested romantically. I both appreciate the effort and attention and simultaneously am irritated that I feel like I should appreciate it, as if I should be grateful for whatever scraps come my way, with no determination on my part of whom I might want to spend time with. The more comfortable I get with the idea of being alone, the more irritated I am at the years I have spent believing this, years in which everyone seemed to partner off and I felt grateful for whomever was left to spend time with.

I have some of the same issues with my friendships. I also have felt obligated in that realm to give largesse, whether it be knowledge, connections, driving, a place to stay, or parties, with little expectation of return. One of my kindest and most moral friends told me a few weeks ago that I could afford to be a bit more “mercenary” in my friendships. I agree to a certain extent, yet I kinda hate that we have become such a mercenary society in general.

On thing about all my current acquaintances is that they are kind. There is no backbiting or “frenemy” type behavior, which is an enormous relief.

I put up with a lot of that from a “friend” a few years ago because she was connected to a larger social scene which intrigued me. I loved having that connection; someone to go out with and with whom to dissect the scene. But she was unkind.

My connections are now isolated… a person here, a person there… none connected to each other or a larger social whole of which I am a part.

context clues

When I look back on the men I’ve fallen for in the past, almost to a one they were part of a social scene, a setting, or an activity I found exciting and enticing. That’s probably one of the reasons online dating never worked that well for me. Meeting someone in isolation didn’t provide the context I needed to generate a sense of intrigue and interest.

The first few years I lived in L.A., I was randomly dating from online, but eventually I stumbled upon a sector of the entertainment industry that was both appealing and, through live shows and social media and podcasts, relatively accessible and transparent. New romantic interests were hatched. For a spell, it was all very exciting, but after several flirtations failed to pan out, I gave up.

It’s no wonder that since I’m currently detached from any sort of consistent, coherent social scene or activity and am leaving my romantic fate up to random encounters, I’m losing my optimism that I’ll ever meet someone. My brain doesn’t seem to know how to form interest in the random guy next to me in the produce aisle or at the gas pump.


What drives men over 50 to pursue women is as primal as social. We’ll always be hunters. Over 50 men are able to start second families, albeit with younger women, but not the other way around. My point isn’t what’s fair or unfair, but rather that many boomer men date younger women exclusively, relegating a vast number of incredible boomer women to wonder if or when men will ever “get it” when it comes to what they’re missing in terms of dating, sex and relationships with women their age.

cat and mouse

It should come as no surprise that the dating landscape has changed significantly over the years. Just as quickly as technology advances, the speed and structure of romantic relationships appear to have done the same. While I have had a vague idea that the times have changed, it wasn’t until earlier last week when I was in a male colleague’s office discussing heterosexual relationships that I came to a startling realization. Apparently, I’m living in an alternate reality.


Many times my therapy clients ask me quite earnestly what they should do, and my thoughts on their situations. Too often has a female client tearfully recounted tales of trying to message a guy, make things work, and do much of the legwork only to be brushed off or entirely ignored. It’s disheartening to hear this and their justifications for their intended’s behavior. “He’s just so shy. Maybe he’s aloof. Perhaps I didn’t try hard enough.” My secret hope is that they simply aren’t engaging with anyone who ascribes to games of cat and mouse. And then I hope they find someone better and more deserving of their affections. Open dialogue and honest communication seem to be the exception and not the norm too many times in their encounters with the opposite sex.

getting over it

By my reckoning, here are some things I have “gotten over” in the past decade:

1. Getting over the need for a social scene, getting over the need for a social group, getting over the need for a best friend. All while getting over the idea of a close and supportive family of origin.

2. Getting over the idea that there is an ideal place to live. Some are more suited to me than others, yes, but all seem to involve significant trade-offs.

3. Getting over the idea that there is an ideal job. Again, some are more suited to me than others, but all involve the daily grind of solving one problem after another, eight hours a day, and all involve a certain amount of indignities suffered at the hands of the public, bosses, and co-workers.

4. Getting over the realization that I have ended up becoming the type of person whom, at least in some part of my youthful psyche, represented the worst sort of loserdom: single and childless and without some sort of glamorous career to compensate.

5. Getting over the idea that I am guaranteed to find a satisfying romantic relationship, despite being just as able to engage in one as the next person.

6. Getting over the idea that I can truly rely on anyone but myself.

These are pretty big things to process, and it certainly took some time, time that others were often too impatient to grant me:

Being told to “just get over it” is devaluing. It implies that I am making a mistake in processing an event. It indicates that something is wrong with ME because I am in still confused about something that has not been resolved. The statement is emotionally abusive. – See more at: