Eventually, I Find a Match

If you haven’t read the first part of this series, My Mis-Adventures in Online Dating, check that out first. The story will make more sense. 

One of the things I take great pride in is the fact that I’m a quick learner. I created a profile on Plenty of Fish (PoF) without having any clue what I was getting into. After only a short while, I developed some skills and gained some experience.

I decided to put this new-found information to the test.

Of course, PoF was a bust at this point, so I needed a new platform. After doing some more research, I settled on OKCupid.

One of the things I found appealing about this site was that they had an involved questionnaire that supposedly was more accurate when it came to matching me with potential mates. It still had the other filters, such as distance, education status, height, etc., but then it proclaimed to go much more in depth.

This was quite different from PoF. They had nothing of the sort. It was just a free for all for finding someone you might be interested in based on photos and their profile—which may or may not tell the truth (I’ll get into this in a later blog post).

Getting Started on OKCupid


As I set up my profile on the new dating app, I already knew that I wasn’t going to pay for anything on the site. I also told myself that it was okay if I didn’t respond to every person who messaged me. This actually turned out to be a lot harder than I expected, but I’ll get into this later.

What I found out during my trial-and-error period is that if you don’t pay for any features on the site, people can only message you if you form a “Mutual Match.” That means if they like you and you like them (blindly at this point, since you can’t see the photos/profiles of people who like you), then you can start chatting with one another. 

However, Cupid has an “Introduce Yourself” feature. If you liked someone, you could send them a quick message to say hi, or whatever. If they liked you back, then you could start chatting. It reduced a lot of unwanted and unsolicited messages that made me feel obligated to reply to.

In PoF’s defense, I should let you know that as a paid member, I had the option of using a feature that only allowed other paid members to message me. I turned this on and off several times, just to see how it worked, but it still led to getting unsavory individuals messaging me.

Things Go Slower


Cupid was a much slower site than PoF. The first 24 hours weren’t the most active, which made it feel less overwhelming and stressful. Likes came in slowly, and a few introductions showed up here and there.

I would say that within the first 24 hours I did receive a message, to which I replied, even though the guy was an occasional smoker and a few years younger than my target age.

I was still struggling with some boundaries at this point. Plus, I was just sure that I needed to find someone to help me get on with my life, and how did I know this wasn’t that guy?

It didn’t take long. It became apparent that we really didn’t have a lot in common.

With things moving slower, this gave me a greater sense of control. I was able to go through the stacks of matches presented to me to find guys that fit my personal preferences. I even took the time to send an introductory message or the first message if there was a mutual match (which didn’t happen often).

Of course, I’m not one to be boring. I refused to send a “Hi,” so I found some fun ice breakers to send. I would send things like:

  • What song do you think would be playing on repeat in Hell?
  • If you could start a charity, what would it be?
  • If you had an extra hour each day, how would you spend it?


I would also read through their profile to find something that sparked my interest and asked about that. For the sake of experimentation, I think I might have sent a couple of “Hi” messages and maybe a few “How’s your day going?”

I had to see if one message or the other was more successful in getting a response.

Hello? Is This Thing On?


It didn’t matter what I sent. More often than not, I was ignored. Which is probably only fair because I ignored a lot of people as well.

I did talk to a few guys, but it didn’t take long for the conversations to get weird/uncomfortable or just fizzle out.

One guy was a professional student living about 1.5 hours away. He seemed incredibly nice and kind at first, and we chatted for a while. Then, the conversation turned to when we could become physical and how he didn’t mind the drive as long as I was willing to put out.

I’m not a prude, but after only a short time of communicating, this seemed really fast to me. And I pointed that out. And—again—the pandemic. 

He mentioned that at some point this would be an important part of a relationship, to which I agreed, but not tomorrow. He said when I was ready to change my mind, I could message him back.

I didn’t.

I was talking to another guy who claimed to be a horror fan in his profile. Since I also like horror films, I thought it would give us something to talk about. That conversation didn’t last long. It was so short, I don’t even remember what was said.

Which, side note, reminds me of a conversation with a guy on PoF. He started messaging me because he noticed that I like horror films, and, at first, he was engaging and fun. We talked about many different movies and what our favorites were. It was enjoyable.

Then, out of the blue, he said: “Does watching horror make you horny?” To which I replied that it didn’t (because I watch horror to discover the things that scare society). His response was that it must be the naked girls, but things became uncomfortable after that, so that conversation ended.

Back to Cupid.

Most of the conversations on Cupid were forgettable. Even though I had the ability to set filters for the types of guys I was looking for, they were ignored just like they were on PoF.

According to the sites, this is because they want all users to have an enjoyable experience, and the filters might limit the number of matches that I am shown. More often than not, this is because there’s a small pool of people in the area to pull from.

This makes sense, especially since I don’t live in a big city, but I don’t want to be shown random guys because it supposedly makes for a better experience.

It doesn’t.

It makes the process frustrating because I’m shown options that I have no interest in pursuing.

I Find a Match


Eventually, I was matched with a guy who ticked all of my requirements (or at least most of them). For the sake of these posts, we’ll call him Milton.

We formed a mutual match, and after reading his profile, I felt like my patience had finally paid off. He wasn’t looking to get married again (neither was I), but he wasn’t looking for hookups, one-night stands, or flings (neither was I!). He just wanted someone to talk to and hang out with (so did I!).

His profile pretty much read like mine, so I said yes.

The only thing that could be perceived as problematic was that he wasn’t looking for someone who had kids. His was grown and out of the house, so he didn’t want to raise anymore. I totally understood that, but since the conversation was starting out online, what did either of us have to lose?

When the “Introduce Yourself” box appeared, I had no idea what to say. It was late, so I decided to go to bed and write something the next day when I was fresh.

He beat me to it. His message was vulnerable and charming, and I found myself liking him even more.

Long story short, we started messaging every day. After 3 weeks, I sent him my phone number so that we could text.

Then, we decided to meet in person.

But I won't be telling you that story. Instead, I'm going to talk about my Elite experience!

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