Jill, what was your most awkward date like?
Episode #
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!

Hear more by listening to the full podcast.

How to listen

Find us anywhere you download and stream your favorite podcasts:

Start your story

Write your story

As you may know, you can use Storyworth to write stories privately and have your stories compiled into a beautiful keepsake book.

Storyworth Book Mockup
Join the next season

Do you want to share one of your Storyworth stories on the podcast?

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.