I’m paying $21.00 a month for the privilege to virtually wink at guys over the world wide web, which is, quite frankly, a bit dumb because a virtual wink accomplishes nothing except to put a deflated ball in another person’s court, and I’m not really one who can afford to put any ball in another person’s court.

Trust me. When it comes to mutual attraction, I throw sticks. Not boomerangs.

And yet, with a few words of encouragement from my sister, who met her husband online, there I was—communicating with strangers.

Within the first week, I regretted including information on my profile that led to messages such as: “What are you going to do now that winter is almost over, ice ice baby? ;)”

One guy, who described himself in his profile as having a “prophetic style,” began emailing me jokes (and nothing else):

What did the frog do when his car broke down?
He toad it.

What’s the difference between dating and marriage?
Dating is a dream. Marriage is a wake-up call.

I stopped responding, so he asked me to marry him.

I went on a date with a man who had the same name as the most recent bachelor. When I met him at the restaurant, he gave me a rose.

A couple of my friends activated accounts at the same time, and one of my friends and I discovered that we’d both been emailing the same guy. He asked my friend out for coffee, and their conversation went something like this:

“A couple of my friends are on there too,” she said. “Like my friend Cassie. Maybe you’ve talked to her?”

“Nope,” he said.

Two hours later, I guess he figured he liked my friend (smart man) and decided he needed to be honest.

“Okay,” he said. “I may have talked to your friend Cassie. You both started talking about ducks at the same time.”

They’ve been on a few dates now. Somehow, they’re both what the other has been looking for. At least for now. And possibly a week or two or ten from now. Maybe a year or decade or quarter of a century from now?

“What are you looking for on here?” began a rapid conversation that progressed from emails to a series of late-night texting conversations, a walk around a lake, a handwritten note attached to a peppermint mocha, silence, and then a nuclear explosion of an argument.

Which was super stressful and confusing because we had only been talking for ten days.

There’s a good reason for dating and even better reasons that dating relationships end, but even when I’m living in the friction of something that’s not working, I always wonder at what point I question someone or something because of a determination against settling. Every time I have doubts, I ask myself where the line is between settling and compromising. Is this really not working? Are we really not right for each other? Or am I just unrealistic, idealistic, and CRAZY?

Sometimes I think I have a better idea of what I’m not looking for in a relationship than what I am looking for. One of my friends on Tinder vows that she’ll pass on any guy with a fish, a dog, or a kid in his pictures. Personally, I stay away from the mirror pics. Somehow I believe that online dating, which provides a supermarket of people all searching for the same thing, perpetuates my pessimistic approach.

Mirror pic?


Loves Twilight?


Shares custody of his dogs with his ex-wife?


At what point do my hesitations become my own failure to allow people to be people? To allow for something unique and unpredictable? To allow for an adventure, a new hobby, a new perspective, a challenge?

“I’m not sure what I’m looking for,” I told Mr. Peppermint Mocha. “My sister once said: When you know, you know, you know? And I said: No. But I’m hoping that I’ll know what she means someday.”

Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

post calvin direct

Get new posts from Cassie Westrate delivered straight to your inbox.

the post calvin