I’ve tried it twice. The first time was shortly after the loss of my husband. I thought my education and experience as a psychologist would give me an edge. I read profiles with interest, trying to screen for personality and mental disorders. I combed their word choices, preferred frequency of engagement, and personal history description for clues, much the same way I would when sitting with new clients.

I soon learned the context contaminated the data. Instead of looking for help, these individuals wanted to convince me of their choosability. They were making a sale – not of a product, but of themselves.

They were withholding essential pieces of information. It was only after the fact that I learned critical data that drastically changed their suitability.

It wasn’t until our first meeting that I learned how one date had spent nearly a quarter-million dollars fighting ongoing custody issues with his ex. Another revealed over a steak dinner that he was homeless, on disability, and living with his adult son. Some men showed up heavier or older than their photos. Others disclose that they don’t own a car or were between jobs.

Then there’s the problem of when to allow oneself to become emotionally invested. Texting, calling, and emailing new matches feel authentic and real. In my mind, I begin to create an image of that person based on the tidbits I’ve gleaned.

I feel like I know this person, and then we’d officially meet. Most are nearly unrecognizable from the mental image I’ve created. The unconscious mind’s propensity to fill in the missing data has worked against me. It has used my wishes and desires to conjure a construct of someone I long to meet.

I suspect the same happens for guys. One particular date and I texted a bit and then decided to meet for drinks. After a very uncomfortable forty-five minutes of conversation, the guy looked at me and said, “Shall we call it?”

The older we are, the more difficult the process gets.

Middle-aged dating only compounds things further since we come with more baggage. We’ve experienced one or more failed relationships, often have complicated family situations, and are at an odd spot in our careers. Our lives are busy and full of obligations. Our interests and values are more rigid, which we try to express by posting our political views, dislike or love of cats, smoking habits, and the number of tattoos. Somehow we hope listing these will attract the right matches.

None of this is working. My two attempts at online dating have shown me what a dismal failure this system is.

No wonder most men have resorted to using online dating as a booty call. They have changed the question from, “Do I like you enough to try to have a life together?” to “Do I like you enough to want to have sex with you tonight?” The second question is a much easier one to answer.

There’s no easy solution in sight.

Looking at this problem, I don’t see an easy solution. Maybe those of us who are single later in life cougar lifeA should bag the idea of finding a second or third love. Perhaps these days, with little opportunity to meet other single people, it’s too remote a possibility. As much as I hate that idea, I’m reluctantly coming to this conclusion.

Trying to sift through all the noise is soul-draining and exhausting. It’s uncomfortable to invest in the work of getting to know someone only to meet them in person and realize it isn’t going to work. There’s a high emotional toll that comes from having to break it off. And I’m supposed to do this over and over?