Normal Pitfalls of Dating When "Older"

Much has been written about dating older. The main reason, based on my clinical experiences, is the reason adult dating is stressful is that you are meeting the person, and the person’s entire social history and memories. Wishful and magical thinking create the need to meet an emotional virgin, which does not exist, unless the date is beamed here frozen, in hibernation from age 10, or younger, from another planet.

Everyone has a story to tell.

Everyone, and I mean everyone, by age 35 ‘has a story,’ (a bad outcome, abuse, trauma, bad luck) and people also change, so who was Mr. or Mrs. Right at age 20 is not Mr. or Mrs. Right at age 45. Yet, we all become set in our ways, so you second guess any new, older relationship, and that is fine, and perhaps you need to be alone, but that becomes lonely, as many singles in high rises discovered during COVID-19 wishing there was someone to talk with, or share an experience. In essence most everyone needs to be with something or someone, a so-called object relation, and if of sentimental value so much the better.

In essence, on an older date you are like a therapist, but absent the training and ethical constraints, knowledge, experience and understanding of human relations, and if of quite different age––more than 15 years apart––have separate learning curves, acquired tastes, and codes of conduct from the ever-changing culture. This age discrepancy causing relationship problems is quite normal, and to be expected, but is painful if you are simply on different wavelengths through no fault of your own.

Life and social norms are unfair. Generally speaking, across the planet, older man may court a younger female––within evolving limits, intestinal fortitude, and a legal retainer––but an older woman dating a younger man, no matter how open-minded is society still seems like a cultural taboo, or labeled in the pejorative: a cougar versus a lounge lizard. A cougar has a negative connotation.

Here is a dirty little secret you already know: People really date for companionship disrupted by sex: from lust to limerick, but at the end of the day unless you have as much to talk about after sex as before sex the relationship of trust will lead nowhere, and what constitutes first base to a home run keeps changing. And many people are simply shy or introverted, or if artistic need space and solitude to think. For these reasons, many really nice people are alone: once burnt, twice shy.

Once set in your ways, a new relationship may also disrupt the creative imagination in your field of choice given that you are now thinking about the other as much as your work interfering with flow, especially being so accessible in the Digital Age. Many great dates simply do not realize this flow factor for fear of losing their leading edge, or are willing to invest in the emotional time it requires to establish a new relationship.

And then there is information overload, and disrespect. Many older people literally do one of those background checks on the prospective date ruining the mystery that should unfold like peeling an onion. If you know too much too soon it is awkward, and paranoid. In fact, in therapy I do not have a new client complete long forms. I want them to share with me in their own way, and timing what is important for me to know at their pace. This sharing patterning makes a therapeutic difference in assessment and outcome.

Dating an older person can sometimes feel like a therapy session.

Therapy is not a date. In therapy the rules are clear. I have no obligation to share my life––a blank slate. The therapeutic relationship is asymmetrical monetizing insight culminating in effective change. However on a date with an older person is like two therapists interacting deciding who is the client, and who is the patient. It is confusing, and in real life is labeled a control freak, or a person who does not listen. If you want someone to like you, have the other talk about themself whereby increasing intimacy based on social psychological research of how to relate and 'connect.' Every salesman knows this trick of the trade.

Even if you seek to make sense of the other––but your own mixed feelings interfere––or may facilitate, great, you are always thinking why is this person here, what do they need, and what is my opportunity cost?

The dating game is in the unraveling of each emotional life-history factor, but this unraveling is incoherent. The process is haphazard, and strained, and filtered through individual and dual memories. A dyad is formed. The psychological sophistication to make sense of it all inside any one date is enormous, and is why dating is confusing, and often later avoided or not worth the hassle.

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Here is the practical problem. If experience is interpretive, and memories fallible, these overlapping factors become a recipe for fate, and is why emotions are high in dating juggling hope, abandonment, jealousy, fear, acceptance, and denial making some first dates better than others.

The odds of a second date are .25

It is obvious, or becomes obvious, that by a certain age a person is not a gift in a box whose contents you can unwrap pure and untarnished. Everyone you meet has a unique life history, with the dating game the disclosure of this past––whether true or not––but as told by the person to you. A high EQ, emotional intelligence, provides some advantages in these ambiguous social situations.

The date exposes you to multiple interpretive versions of one life story. If your date has a dysfunctional past, or that is your sense, you then have to decide in real time to move on or not, and the other person has the same problems about you––if it is worth the effort to deal with this past, or to rehabilitate and nurse the (supposedly) damaged person back to interpersonal health. This makes the odds of a second date .25, or a “yes-yes.” Let’s meet again.

However, keep this in mind. If in doubt about their mental health you are not their savior, or their therapist. If after the first or second meeting, if something smells fishy, don’t allow it to go on for longer than that. If you throw up your hands in frustration, or have a negative gut feeling do not feel guilty. You originally had no idea what you were getting into on the first date, but you gave it a shot––and why not––and now you know more than you wanted. In this case loyalty is less a virtue than naiveté. Life is too short to waste three months at a time engaged, enraged.

A date is about the near future––a near future that may well never be the same again if the person disappears, or is disappointed or rejects you. This decision matrix is subjective making attraction irrational and illogical, but at the same time you cannot force someone to like you let alone love you.

Once a lifestyle is established it is hard to change on a dime. It is impractical to think that after a first date magic happens, that the person suddenly drops their life suddenly available at your beck and call. This is especially true today when many people already have a life, are multitasking, are self-sufficient, are drawn to the shine of cyberspace, or have dropped out of the dating scene based on prior, ambiguous, negative experiences.

Older people seek what does not exist: the emotional virgin.

It is safe to say that people would secretly meet someone who is emotionally intact–an emotional virgin–who is not corrupted, tainted, or otherwise indelibly stained from a previously good relationship gone sour. Get over it. It isn’t going to happen. That person fails to exist.

Yes, you would rather be the very first one, as if they have been alone on an island, or in a cave. And you wouldn’t mind if they crave you above all others, and once secured would orbit you forever, but even in physics is gravity, thermodynamics, and entropy to bring you back down to earth.

No matter the roles we play, and the hats we wear, we are all social animals. A contented, older working relationship often boils down to change and happenstance that you even met–what are the odds–given all of life’s modern distractions, ideological chat rooms, and shiny technology more enriched and controllable than a human being with multiple operating systems.

Older relationships are not rocket science, but they are harder. All you really desire is one person in the universe to believe you special, offer a kind word, listen, share, of good character, and that is all enough.