Jill, what was your most awkward date like?
Episode #
14
27
Min
Thursday, March 2, 2023

Jill, what was your most awkward date like?

The Storyworth Podcast
Episode Description

Dating sites can be overwhelming for anyone, but especially for those taking a chance on love later in life. Our story this week centers around one woman’s journey to find a new companion after a decades-long marriage.

Who doesn’t love hearing an awkward date story? We all secretly delight in all the gory details of other people’s dating ordeals. These kinds of stories usually involve a pair of twenty-somethings fumbling to find love. But I can confirm the ups and downs of dating can strike at any age.

So three years after Stuart died, I decided I’d had enough being on my own. I wanted to open up my heart again to a new relationship. But I was interested in something meaningful. More than the quick flings some local men seemed to think I needed. Despite my repeated refusals some men never gave up. So I finally took matters into my own hands and turned to a popular online dating site.

I pieced together my write-up and attached a few photos of myself and winced as I activated the account. My profile went live. This was really happening!

Then the website’s algorithm selected a few member profiles deemed compatible with mine. As I scrolled through my matches, I began to notice many of the men’s profiles sounded the same. Especially their descriptions of the ideal partner: “Must look good in jeans and a black cocktail dress.” I rolled my eyes, already beginning to question the process.

I studied more of the men online. It was funny to notice their patterns, like the fact their descriptions seemed tailored to what they thought women wanted to hear. I came across saccharine phrases like, “I love long walks on the beach holding hands,” or “My ideal date is a romantic evening in front of the fire with a glass of wine.” When you’ve read the same lines a dozen or more times across different profiles, you start to suspect they’re just designed to attract women, rather than offer a genuine reflection of the person. These “stock phrases” were my cue to stay clear and click on to the next profile.

After a lot of wading through lackluster profiles, I found someone promising: David seemed honest, direct and sincere. I found myself smiling as I read through his information. He was interesting and thoughtful. His photos offered a glimpse of a well-dressed man with a pleasing face and friendly demeanor. It was so refreshing to find someone I could envision spending time with. I made the bold move and sent a quick message off to him…and he responded!

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