Dating over 40: The Spinster Chronicles

Wondering what the truth is about dating over 40? Maybe you are in the throws of Bumbling or have your own fair share of Tinder disasters to share? We just know you’re going to relate to our new column: The Spinster Chronicles! Headed up by Jennifer Walters – a confident and gorgeous 40-something woman from North Carolina. Sadly widowed far too young, she continues to work through her grief and ‘is figuring out how to make the most of life.’ While doing this, she has diarised her hilarious dating over 40 disasters on social media, and now we are bringing them to you at 40 Now What!

The truth about dating over 40

My real first date was with a guy I met on an online matching website. 

His profile said he was a six foot two redhead who was fond of the local wine bar that I often frequent. We decided to meet there for a glass of wine.

I arrived early, so I could pick a good table and have a few sips to calm my ‘haven’t been on a date in a long ass time’ nerves. 

Thirty minutes and a glass later, I got a text from Redhead saying he was outside, but not sure if he should come in. I told him that he should. He asked if I was sure. I said yes while wondering if he was hesitant because he had phoned a friend that was acting as his informant on the inside, who told him I looked like a troll.

I finally convinced him to come in, but I didn’t see him. Instead, a five foot two man in a shirt two sizes too big sat at my table. I thought it an odd coincidence because he too had red hair. To my dismay, this little man introduced himself as Redhead as he sat down.

Redhead ordered himself some wine. As we chatted I learned he didn’t seem to have a job that was real, a kid he didn’t see very often, and a dog he really thought was the cat’s pajamas.

We wrapped up the night with him giving me a pat on the back and the words ‘let’s just use this as your first practice date.’ He then left me with the bill, a tremendous sense of bewilderment, and a promise to myself that if a leprechaun ever showed up to meet me for a date again, I’d pretend I didn’t see him or his lucky charms.

16th January 2021

I went on a date earlier this week. It was with a poop doctor I met online. And although I would never admit to online dating years ago before I was married, apparently that is what people do now, because for some reason men no longer believe in actually talking to a real life woman face-to-face without first spending weeks on meaningless chit-chat hidden behind an online profile picture. 

He spent the entire night talking about his job and using words that you wouldn’t understand unless you too were a poop doctor, interrupting my responses whenever he shocked me with a question with questionable interest in anything about my life. Then he told me of his incompetent assistant, who was obviously hired because she’s so pretty, which he stated I can probably relate to because my looks have surely helped my career too. He wore pants with a subtle checkered pattern which I chose to accept as acceptable, because the print was subdued and his, well, his biceps. I spent most of the night trying to figure out if he was a douche, nervous, needed a recommendation for a good therapist, or maybe worth a second date because he was kinda funny. 

The next evening I sent him what I thought was a very thoughtful text, full of recommendations of things to do in a city he would soon visit. He responded the following evening, with a meme. WITH A MEME. I’ve not heard a peep since, which is completely on trend when my dating life for the past two years. 

Between the men who don’t actually ask me out after endless flirting and these weirdos that I never hear from after a first date, it’s a good thing I have my amazing imaginary knitting circle friends and invisible hairless cats. I think I will stick to evenings alone with my television programs and start looking into joining a bridge club. 

Who can teach me how to play dating over 40?

‘I have such a magnetic draw for oddballs.’

22nd January 2021

I went for a bike ride today. That’s a lie. I don’t ride bikes. I was really just walking my dog.

During my casual stroll, as per usual, I was reading my book du jour on my phone when a young man who looked like a cross between Jack Black and Napoleon Dynamite rode up beside me on his ten speed.

He stopped next to me and proclaimed, loudly and enthusiastically, ‘I love older women!’

I asked him how he knew I was older than him and he told me it was obvious and he’d love to take me to dinner.

I told him I don’t go to dinner with younger men who I meet on ten speeds while walking my dog.

He said please. I said no thank you.

Jack Black and Napoleon Dynamite then pedals off, leaving me feeling slightly flattered, slightly insulted, and wondering if I should finally learn how to ride a bike, and why I have such a magnetic draw for oddballs.

You can follow Jennifer and her dating over 40 mishaps on instagram @spinster.chronicles and follow us on instagram @40nowwhatmag.

Have you had any dating disasters in your 40s? Comment below.