My Mis-Adventures in Online Dating

I’ve always been wary of online dating sites. I’ve heard too many stories about women meeting unsavory men or dealing with creeps. I also watch a lot of real-crime TV shows. There also seems to be a desperation factor associated with creating a profile, and I never wanted to come off as desperate.

I’m from the generation that saw the rise of the internet. I’ve been there from the beginning and have watched it evolve. I’m comfortable being online. I have no problems meeting people online, but the thought of forming a romance wasn’t appealing.

Of course, over time, my thoughts and ideas on that notion changed.

Over the summer, my Outer Child convinced me that I had to meet someone new. Since I work from home and, you know, the pandemic, my only option was to sign up for dating apps.

I don’t drink, so going to bars is out of the question.

I’m not religious, so church? Ha! Not gonna happen.

I live in a fairly small town that doesn’t have a lot of clubs or organizations to join (trust me, I looked), so what was I to do?

I wasn’t comfortable with the decision, but I had read several articles about how the perception of meeting people online had changed. It was no longer stigmatized. In many cases, it was the norm. I wanted to move on with my life, and I convinced myself this was the best way to do that, so I did some research.

I’m not the type of person to just jump in and create a profile on any old dating app. I read a lot of articles and reviews about which ones are the best before finally deciding to download one.

The First App Was a Bust


Honestly, I don’t remember what the name of the first app was. I will tell you, though, that within an hour, I had deleted my account and uninstalled the app. The men I was matched up with absolutely did not meet my criteria.

Here’s what I was looking for in the men online:

  • Between the ages of 40 and 52 
  • Had at least some college (keep in mind that I have a Master’s degree, so education is very important to me)
  • Non-smoker (I would not budge on this at all)
  • Preferred non-drinker, but it was fine if they occasionally imbibed
  • Preferred taller than me, but it wasn’t a deal breaker if they weren’t (I’m just over 5’9”)
  • Preferred someone non-religious (it would just make things easier)

Where the person was located was also a big factor. I didn’t want to traipse across the country looking for love, and it was damn-near impossible to do with COVID raging anyway.

When it came to the first app, the vast majority of the matches I was sent were smokers or undereducated or both. This is not a judgement on the type of person they are, this is a personal preference. I wasn’t going to lower my standards, so I removed the app so that I could find someone more on my level.

My Second Attempt


After doing some more research, I settled on another dating app (Plenty of Fish [please note that I will not link to the apps because I don’t want to promote them, but I think it’s only fair that I let you know which ones I tried), downloaded it, and set up my profile. It said in the description that the first 24 hours of being on this site are the most active, and they weren’t kidding. I had to silence the notifications because my phone was about to explode.

During my research, I came across several articles that said to get the most out of the dating app experience, you are supposed to respond to every message you receive. Since it’s so hard to really know a person from a few photos and a short profile, engaging in conversation helps.

Let me tell you something: this is terrible advice to give someone who has had issues with creating and maintaining boundaries. I also have people-pleaser tendencies, so I was giving guys who didn’t deserve chances a chance. This didn’t make my experience pleasant.

The other thing that made me feel like I had to talk to people was the fact that I had paid for the site. When you have a free account, you get a notification that someone liked you, but you can’t view their profile or their photo. I wasn’t going to go into this blind. I needed to know who was liking me, so I decided to go for the paid option.

I misunderstood the payment options, so I wound up paying for, I think, 8 months of services. It seemed excessive, but once you’ve sent your payment information, you don’t get refunds.

Meeting My Matches


One of the first guys I met on the site wasn’t my type at all, and he lived well out of the range I was willing to drive, but since I was talking to everyone to potentially find Mr. Right, I engaged him in conversation. He was pleasant at first, asking questions and doing the whole get-to-know-you thing.

At one point, he mentioned that he was really enjoying talking to me and that he hoped it would continue. Within 30 minutes, that completely changed. Here’s the exchange (warning: bad language used! His message is gray, mine is the greenish): 



Now, I’m not sure why he thought he could decide if I was ready to meet new people or not, but at that point, I was done. Three days after this conversation, he sent another message trying to engage me again. I ignored him. 

Since the first few days are the most active on the site, I had another guy message me to tell me that I was a “cutie.” That sat really wrong with me. I’m in my 40s. I’ve outgrown the “cute” stage by about 15 to 20 years. I mentioned that to him, thinking that maybe he’d like to try again, and he sent an apology with an “you’re awfully sensitive as well.”

And that was how that conversation ended.

Another guy commented that I had a “bangin’ body,” which I don’t know how he could tell because I wasn’t wearing anything skintight in any of my profile photos—and most of the time the pictures didn’t show me from the neck down. When I asked him to not go there on the second message he sends me, he asked: “What are ya a nun?” Grammatical errors were included.

That resulted in a block.

Within two conversation bubbles with one guy, he asked if I would be embarrassed to have a 5’7” stand next to me in public. At that point, I knew nothing about him, but I sure as hell knew I didn’t want to deal with his height insecurities. I didn’t respond to him at all.

I was able to engage with a few individuals who were respectful, but I could tell from the beginning that the conversations weren’t going to lead anywhere. I hate one-sided conversations. If I’m the only one asking questions, I’m not going to keep talking to you. The goal is to get to know one another, but if you can’t ask me about me, then that signals that you’re not interested.

One guy I talked to did know how to ask questions, but he was farther away than I would have preferred and trying to move things too quickly. Within the first exchange, he was talking about me driving the 1 hour and 20 minutes to meet him.

Now, I completely understand that the point of dating is to eventually meet up in person. However, with a pandemic raging and long distances to drive, I preferred to chat online for more than an hour before taking that step. And I mentioned that. He said he understood, but constantly commented about when we could meet up.

I tried to reject him kindly, but it got to the point that whenever he saw me on the dating app, he would engage me in conversation. Due to my personality quirks, I couldn’t just ignore him, so I would get sucked into talking to him.

It got to the point where I didn’t want to be online at all for fear of running into him.


My Initial Beliefs Were Reinforced


My initial interactions with matches were cringy enough, but there were other reasons why I didn’t like this particular app. The number of fake accounts was staggering. I would say one-third of the people who contacted me were trying to lure me off the site so that they could ask me for money. I was ready for it, though, so I didn’t fall for their trickery.

Out of curiosity, I did a search to find out how successful scammers were in getting people to send them money, and I was shocked by what I found. In 2019, it was reported that people lost more than $200 million to romance scams.

$200 MILLION!

Says a lot about people. There are a lot of lonely people in this world looking for a connection. It also shows that some people have no scruples and will take advantage any chance they get. It’s sickening on so many levels.

In addition, the filters were worthless. They only work when it comes to showing me guys I might be interested in, but if someone is interested in me, they can like and message me whenever. They don’t have to be in my 100-mile radius or be non-smokers or whatever other filter I set. Because they are shown people who match their filters, and they might not have set any. This troubled me a lot. I was contacted by a lot of men that I wasn’t interested in at all.

I did not enjoy my experience on the Plenty of Fish dating app. It reinforced my initial beliefs that dating apps are full of creeps.

I wasn’t quite ready to give up, though. My Outer Child convinced me that there was still hope, so I decided to conduct an experiment. That involved signing up for another dating app.

Tune in next week when I share what I learned from OKCupid.

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