Calculated Risks: Online Dating

It’s been over a year-and-a-half since I started down this online dating path. I’m more used to the course now and I look back over the distance I’ve traveled, a baby boomer on a different kind of sojourn. Considering my experiences, and those I’ve heard about from friends and family, the notion of calculated risk comes to mind.

I like the way calculated risk is defined on “Writing Explained”:

“A chance that is taken after a careful estimation of the possible outcomes.

Examples are given followed by the summary statement:

“An action that someone takes that might not succeed but is worth taking the chance.”

Photo by Pixabay on

When I created my profile on my first dating site, I decided it was worth taking the chance. We were still locked down in the pandemic and there was no other way to meet people. For fifteen months, I couldn’t even get to know guys in the usual, in-person way at my social dancing venues. And now, even as things have opened up and we’ve been able to return to some of our pre-Covid activities, I realize in today’s world there are people we’d never cross paths with if it weren’t for the online resources.

Men and women whom I’ve talked with, some who have experience with online dating, some who don’t, lists some of the perceived risks. Women often mention their personal safety, noting there’s a “lot of weird people out there.”

I agree that there are weird people out there, but that hasn’t been my experience. Sometimes I think they’ve seen too many Dateline shows of unexplained disappearances and bodies that have turned up.The possibility of danger is always there, whether you’re going to meet someone for a coffee date or you’re grocery shopping at Harris Teeter; something could happen because there are people who do bad things.

In an article written by John Spacey, “3 Examples of a Calculated Risk” on

he describes the risk faced by big wave surfers who regularly enter turbulent waters. While they face risks, they mitigate those threats. They fine tune their surfing skills, stay in top physical condition, do mental preparation, never surf alone, and consider what could go wrong and have a plan for how to survive each scenario.

Photo by Oliver Sju00f6stru00f6m on

Likewise in online dating, I’ve found ways to mitigate threats. Over time you learn to recognize patterns in profiles of scammers or questionable people. They have the Hollywood-type picture and appear ten years younger than their stated age. They say they’re from a small town in North Carolina but have a European background and speak several languages. Eventually you don’t waste your time even looking at those profiles and just click “Skip” and move on to the next potential.

Besides the Hollywood good looks, another pattern that emerges are guys who quickly want you to get off the site to message them or “my uncle who likes your picture but doesn’t have a subscription to this site.” Some immediately give out their phone numbers saying to text them— skipping over any semblance of the typical, getting-to-know-you messages. When you’re just starting out, it’s easy to not see the patterns–you’re so eager to put your feet in the water.

Like the surfer decreasing the threats, with online dating you can prepare a safety plan for how to escape a threatening scenario. Most people I know insists on meeting at a safe public place, which for me has been coffee at Panera. When I’ve met guys for hikes in public places, I texted my sister and a friend to tell them where I’d be and who I was with. I always have the option of exiting any date that feels threatening or just isn’t working; there’s no obligation to stick with it. This is an advantage compared to dating back in the day, when you were stuck with that date until they drove you home.

While I’ve met some nice guys and I’ve not had horrible or threatening dates, I can’t say that this path has been easy, and many times it’s seemed unrewarding. Some of my friends have become so frustrated they either got off the sites for a few months or altogether.

An article done by Pew Research Center, “The Virtues and Downsides of Online Dating” by M. Anderson, E. Vogels, and E. Turner, takes a look at online dating across age groups. A survey done in October of 2019 highlights perceptions of online dating:

On a broad level, online dating users are more likely to describe their overall experience using these platforms in positive rather than negative terms. Additionally, majorities of online daters say it was at least somewhat easy for them to find others that they found physically attractive, shared common interests with, or who seemed like someone they would want to meet in person. But users also share some of the downsides to online dating. Roughly seven-in-ten online daters believe it is very common for those who use these platforms to lie to try to appear more desirable. And by a wide margin, Americans who have used a dating site or app in the past year say the experience left them feeling more frustrated (45%) than hopeful (28%).

There are both the negative and positive, the risks versus the benefits in online dating.

But perhaps the greatest risk of online dating is the same as traditional dating; you can get your heart broken.

Especially when I first started down this road, I had many nights when I woke up in the middle of the night and had a hard time getting back to sleep. I’d sit in my desk chair and look out into the area in front of my apartment–so still, no one walking their dogs at four in the morning.

One night, I had a low mood after realizing that a guy I’d liked, who’d been messaging me, was likely a scammer. I was disappointed and felt foolish for thinking he was real. I saw how quickly my heart could fall for someone–and in turn, how easily my heart could be broken. Maybe I should get off the site and just take a slower, more traditional route to finding someone. But couldn’t my heart still be broken? I’d known plenty of people who’d dated a real person for an extended period and it ended in heartbreak.

Looking out at the cars, sleeping in their individual spaces, it occurred to me, “When you fall for someone, your heart has to expand–to open up to that other person, to take in their world, and have a greater understanding of your own.” There’s personal growth in that expansion–no matter the outcome, I thought. Calculating the risk, heartbreak is a likely occurrence, but maybe there’s growth that eventually leads to resiliency– a stronger heart.

Maybe it’s worth a calculated risk to continue the path of online dating.

Photo by Bradley Hook on

2 thoughts on “Calculated Risks: Online Dating

  1. Connie, I liked this just for the opportunity to view an angle not considered. When I started reading the thought of calculating a feeling began to morph into a physical part of living that went beyond feeling. Well, I guess that is what you do best. Love and Blessing, and sorry for the late response. John,


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