In a call‑in segment of The Dennis Prager Show, host Dennis Prager talks with two callers—Katie from San Antonio (age 49) and Mike from Chicago (age 47)—about their experiences with online dating and how it led to lasting relationships. Katie explains that after two early marriages that didn’t work, she turned to online dating in her early 40s. The process forced her to reflect on her own patterns, learn to read people without the distraction of physical proximity, and clarify what she truly wanted in a partner. Although she ultimately met her husband in person, she credits the online “minor‑league” experience for preparing her heart and mind for the successful match. Mike recounts meeting his wife on OKCupid eight years ago. He describes a multi‑step communication path—site messages, email, phone, then an in‑person date—highlighting how the platform let them filter for shared values and avoid hookup culture. Their early online exchanges moved quickly from superficial to deeper topics, creating a sense of familiarity that made the first date feel natural. Both stories are presented as evidence that modern, intentional online dating can help people find compatible, long‑term partners, especially when users approach it with clear intentions and self‑reflection.
Chapters
Katie in San Antonio. Hello. Hi, Katie.
Hi.
Hi.
How are you?
Good. Thank you.
So I immediately had to call because yes, I'm in San Antonio, but I'm also a CU grad and I came out of it ironically very conservative and faithful in my religion and contrary to all pre-indicated.
I'd like, that would be an interesting discussion how you survived it. I would be curious actually. But go on about the dating issue.
Yes. Well, so I never, when I was young, really dated very much. I got married very young and didn't do it very well, unfortunately.
How old are you now? Sorry, how old are you now?
I'm 49.
Okay.
Yes. So, and then married again and didn't do it well again. So I stopped and said to myself, okay. I could be upset about the circumstances or realize that I was the common denominator and stop and take a few years and figure out why was I picking the wrong person. Once I did that, I decided, okay, I'm going to get out there and get online. And at that point, I was in my, you know, early 40s, and I decided to do that hard. I dated hard, and it was the best thing that I ever did because It gave me the chance to read people well, and as you previously mentioned, yes, you don't have the distractions of physical proclamation or—
Proximity.
Proximity, thank you, with one another, unless you choose that. But I think the thing that a lot of people are hesitant about is the fact that people put out a certain persona online, and then they meet them, and that's not the reality. Well, I get that, but that's true whether you meet someone in the wild, as they say, or online. People can put out all sorts of fronts about who they are, and it's really about you learning how to discern.
All right, stay on, stay on with me. I am actually interested in your experience. So I'm talking to Katie in San Antonio. She's 49. She, she, you met, you're married now, right?
Yes, sir.
And you met your husband online.
So actually, I didn't. Oh, I didn't.
Well, you can understand why I thought you did. You called up to make the case for the, for dating online.
Indeed. What I would say about that is that the time that I spent dating online prepared me to have my heart open, my mind open. And when I met my now husband in the wild, I was very ready for what he, you know, what, who he was and what he was, because I had taken the time to learn what I did want and didn't want, in large part because online dating affords you the ability to learn about other people sight unseen sometimes, sometimes meeting And by the time I met him, it was just very clear that we were a good match. So it was a really beneficial chapter for me, even though that's not ultimately how I met him.
That's fascinating. So that it's sort of, uh, it prepared— it was the minor leagues preparing you for the major leagues, to use a baseball analogy. Is that right?
Exactly. Exactly.
Okay. All right. Is it— this is going to be helpful to people, I hope. This is the reason for doing this. Mike in Chicago, hello.
[Speaker:MIKE] Hello Dennis, thank you for taking my call. I met my wife online. We conversed for a couple of months without having met and then that fateful day came and we met and 8 years later, next week will be 8 years, we've been together ever since and we got married and Everything that Forbes article listed as reasons people have successful online dating events, I can agree with because I experienced all 3 of them. But also to include, when you're online dating, you get to— I don't want to say weed out, but you get to pick and choose through attributes and different philosophies that people may have. that they post on there before you even start to converse with them. So you kind of get to get a feel for a person before you get a feel for them. And it really gives you the, affords you the opportunity to find hopefully the perfect partner. And I know I did. Um, just a quick aside, after our first in-person meeting, um, I deleted my profile because I realized that she was somebody worth getting to know well, and it It was wonderful.
What website were you on?
We met on OKCupid.
And why did you choose that?
Uh, I didn't want a hookup site, if you will. I didn't want a hookup culture. I was, I was looking or wanting to find somebody that was going to be good to me after, uh, uh, an unfortunate—
okay, I'm sorry I interrupted you. I got that though. So I, I want to walk through this just for a moment. The first contact was email. How does it work?
It's through the site. It's, it's been a while, so I, I actually sometimes forget we met online because it's such an amazing relationship and it's so easy. But yeah, it's through the website at first until we decided to exchange numbers and then we texted for a while and then we talked on the phone a little bit and then we finally, after a couple of months back and forth, we met and it was, it was a wonderful first date.
And the, the, the early communications, to the extent that you remember them, were they superficial, which is very common on first dates in person, or were they deeper?
So the first couple of interactions online were slightly superficial, but we both— now looking back, we both wanted to meet somebody deeper. And so we quickly got into the meat and potatoes of what's important in life. And I can remember at that first date, there was such a familiarity and a knowing of somebody without ever having met them physically that it made that first date that much much easier. And, and I have been going through quite a bit at that time, and I had some physical disabilities that have since been corrected that she was aware of and had no problem with. And it was wonderful.
Wow. And how old are you?
I'm 47 and she's 45. And like I said, 8 years ago next week we met for the first time. And I, I thank God every morning for putting her in my path and giving— I don't think about OKCupid anymore, but I do know that that's the reason that, that she was allowed to be put in my path.
Well, it's a beautiful, beautiful story. Thank you. For the full episode of The Dennis Prager Show, go to pragertopia.com, sign up, and become a full member.
