Dating Adventures From a Woman of a Certain Age: Not Making the Cut

As a woman of a certain age, I am putting online dating men on notice: I will not settle! Many of you WILL NOT make the cut!

At this stage in life, I did not expect to be navigating the dating scene. You see, it’s been nine years since my husband died. My world tilted on its axis and stopped spinning altogether. Grief does that to a person.

Still, I did not get stuck in the dark basement of my grief. Instead, after a few years of serious grieving, I was encouraged to put myself out there and try dating. With shaky knees, I realized it had been 36 years since my last date. Where  was  I to begin? Where does one meet eligible men? Of course I knew the answer to that, and I did not like it. Online.

Oh how I longed for the organic ways before the internet. Meeting at a community event or work, talking, and getting together again to get to know each other better. Then there was (and still is) being set up by a friend. It would be so much easier if the single men looking for love again placed a sign on their chest or on their hats that said “Single and looking for a good woman.”

But alas, such oddities aren’t the way of things. And so, on to the dating websites, I went. Setting up a profile is humbling. How much of myself do I expose? Which pictures portray my best sides? Once live, the looking begins and the notices of likes start pouring in. I was shocked! What man more than 20 years my senior would think I would be interested in them? And why would I be attracted to the guy that just wants a booty call? After all, I was looking once again for love.

Let’s just say it was slim pickens’! In fact, that would be an understatement! So, after trying out a few guys for a while, I find myself once again, for the seventh time, on a dating website. Never mind that after the last serious guy, I had sworn off ever going on a dating site again. The humility and disappointment was far too grueling.  Was  the pounding my self-esteem takes on these sites even worth it?

Yet in a weak moment, while listening to music in a beautiful setting one summer evening, I found myself green with envy at this romantic event at the local winery. I was jealous about all the hand holding around me, and slow dancing between me and the band. I was lonely in the midst of the crowd that surrounded me.

How mistaken I was when I thought it was a good idea to attend alone. My justification: I enjoy a good glass of wine and outdoor music on a summer’s eve. What could possibly go wrong? After all, I had taken my dog so that I wouldn’t feel so alone. Not only did I feel alone, I felt pathetic paired up with my dog, as I was.

To spare my personal dignity that evening, my “never again“ became a “just one more time” on a dating website. And so I set out to create yet another profile. I clearly stated the things that I would not permit in my life. My parameters were set very high, and my expectations were pretty low in the shallow pool of fish that is dating as a woman of a certain age.

This time around, I am not willing to settle. I swipe left on most of the men, especially the men who take pictures in their bathroom mirror, the toilet clearly visible over their shoulder. I bypass men who can’t seem to smile in any of their photos, and try to look sexy as they glare at the camera. Then there are the men who post pictures of their motorcycle, their boat, their camper, and their pets, without a picture of themselves... clearly they are not worth the risk.

I choose not to waste my time on men who can’t seem to ask ME any questions, but happily share a boatload of information about how great THEY think they are. Then there are those whose opening line is “hello beautiful,” and immediately try to get me off the app, wanting to talk on a regular phone or jump to What’s App (almost always a person out of country seeking to scam in some way). I don’t have time for the many men who can say nothing more than “hey” or “good morning," or "what's up?”

Still, there is sometimes decent conversation that happens through the app. When that happens, as soon as it feels comfortable, I suggest meeting for coffee or a drink. One of two things happen here: we meet and check each other out and see if we’re attracted to one another, and then there is a second date. Most times there is not a second date because of how little they chose to prepare for said date. The other thing that happens at a suggestion to meet is that they have an important work project that needs their attention. "When it’s done," they claim, "we can meet." Or, at this point, they share they are currently working OUT of the country and will be back in a few months and can meet then. But in the meantime they still want to communicate and “get to know each other better.”

For the men who agree to meet, many dress like they’re going to do yard work instead of being on a date. The graphic t-shirt is barely clean, and it is paired with gym shorts and a hat, which they do not take off because it’s covering messed up hair. (One guy took his off and it looked like it hadn’t been washed for a while.)

Some first date guys have been pretty interesting. There was the one who held his fork like he was digging in the garden, with his thumb not in use. Or the guy that did not wear hearing aids to the date, and every couple of minutes he had to ask “what” in the noisy restaurant he had chosen. Another guy ordered wings for supper, and then proceeded to eat them as if he had not seen food in days, ending with sauce all over his face and up his arms.

Even the guys that get a second date or more beyond that, tend to talk about themselves more than listen to me. They ask me a question, listen for a little bit, and then go off on another self-centered topic of their own. Rarely am I allowed to finish my sentences and share my ideas. Plus, the guys that were ready for a booty call after one or two dates clearly didn’t listen to what I was looking for in a partner. Or there are the men who got married in their twenties, raised a family, worked hard, and then divorced. These guys swear they will never have another serious relationship again (though are happy to jump in the sack!) Or the men or are "separated" and assure that the divorce is in process.

I don’t need a man just to HAVE a man. I know I have value and deserve someone who values me for who I am. For what I can bring to the relationship. Being alone is the better alternative to settling for a guy who doesn’t see my worth.

Case in point: two serious relationships later, and I am still single. Two men who tried to mold me into the person they thought that I should be. Two men who pulled me away from my friends and family. Two men whose personalities and gas lighting were subtle and persistent enough that I lost sight of my own true self. Two men who looked elsewhere (for women) when I pushed back on their tactics.

I deserve better. I want someone who won’t be jealous of the life that I have created. Won’t be off put when I want to spend time with long time friends who are a part of my support system. A person who allows me to still love my dead husband and the life that we had together, including my family. A man who has a good relationship with his own family, and thus values mine. A guy whose ego lets them love me even while I’m still learning to love them in the new relationship, beyond my husband’s death.

Divorced men, especially, have trouble with this. They tend to fail to understand that my status as a single person was thrust upon me, it was not chosen by me, like their singleness. They lack understanding of the personal experience I struggle with when grief rears its challenging head. When my ever-present grief rises to the surface, it gives these men pause. Like they think it somehow my grief diminishes this new love we have formed.

The thing about love is that the more one loves, the stronger the bond can be with another person. The greater capacity to love again is there, ready and waiting.

I know the universe says that there is someone for everyone, but I’m going to be picky in the looking. For example, I have chosen to pass on the tall, lanky man in a pink suit who looks more like a pimp than someone I would do life with. I have chosen to swipe left on the guy who could be Jabba the Hutt’s younger brother. I have opted to NOT step into the role of Mrs. Santa Claus with the heavily white-bearded man pretending to be in his 50s. Neither have I chosen to match with a guy whose picture makes him look like a ghost who is also likely a serial killer. I have also let Lurch pass me by, even though he liked me first, as well as the guy whose profile picture looks like he’s trying to create the Scream Mask!

Others that have been given the boot are the men who seem too good to be true. They have a polished AI profile and say all the right things when we’re communicating at the onset. The same guys plead over and over to move off the app and onto a ‎WhatsApp platform. I wasn’t always this wise. At the beginning of online dating, I may have been tempted by the attention of these beautiful men. But I have learned it is  most likely false.

As a woman of a certain age, I am putting  men on notice, especially online men. I am picky. I am not willing to settle. I will not be sending you money. I will not wait three months until you return from your overseas trip. I will not date you while you continue to date other women. I will not only do the things YOU want to do, you will do the things that I like, as well. I will not compromise my friends and family to make you feel better. I will continue to love my husband, knowing full well he is never returning. And I will learn to love another because I know there is somebody out there for me. 

And ladies, please don’t settle either! Your own well-being and value are worth more!

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