The Ultimate Misadventure in Online Dating: Too Big to Fail?

He certainly had something big, but it wasn’t exactly what he claimed

Wendy Miller


Photo: glegorly via Getty Images Signature

I’ve written before about some of my misadventures in online dating. Usually, I group a bunch of men together in one story, with just a short tale of what they did that was so memorable in such a bad way.

However, this guy earned a post all for himself. Based on the size of his ego — yeah, let’s go with ego — I don’t think he would have been able to share a post with others. I’ve taken screenshots of my last interaction with him so I could share them in this story, but like the other men I’ve talked about, I will not be identifying him by real or user name, nor will I include his photo. I can assure you that you don’t need me to identify him. If you come across him, you’ll know based on what he says.

And now… on with the story!

Three Separate Dating Sites, Three Separate Matches

I know the first question you might have here is how I could match with this guy three different times if he was so bad. So let me explain a little about online dating for me.

I’ve reached a point where dating is enjoyable but not required. If I find someone and it develops into a relationship, I’m happy to follow that and enjoy it. And if I don’t, I’m quite content with my life as it is. It’s very full with my work, my children and grandchildren, friends, and hobbies.

So when I am scrolling online dating sites, my standards are pretty high in the sense that if someone’s profile clearly states they are only looking for something different than what I want, I keep scrolling. But my standards are also broad enough that I don’t necessarily pay super close attention to photos. This means that I have frequently matched with the same men on multiple dating apps. Their profiles were written differently enough to intrigue me and not seem familiar and I either didn’t pay attention to the photos or I didn’t recognize the guy.

Which brings me to this guy. We matched three different times on three different apps. The first time we matched, and he told me this story, I gave him the benefit of the doubt. I was not interested in his…