What to Do When Online Dating Feels Transactional

My wife and I met through CatholicMatch in late June of 2016. We did our first “in-person” date in late July and we were engaged by mid-December. She moved here in March 2017, we bought a house in May 2017 (I didn’t move in until we were married), and we got married in August 2017. Our first child is due in August, two weeks prior to our first anniversary.

On that level, online dating was a smashing success. As they say, you only need to find that one right person. But my overall online dating experience was also quite morally challenging at times.

I first tried Match.com, but I had a few issues with the site...

My first online dating experience was in 2011. I joined Match.com, and made my profile as Catholic as I could. (I don’t remember the quote exactly, but I put something like: “I support the Catholic Church’s teachings on morality. If you support abortion or pre-marital sex, I’m not your guy.”) I met some very nice women, including one person I dated for some time.

However, that online dating experience had many downsides. Specifically:

1. I take my money very seriously. If I’m going to spend it, I want to get the most value. For Match.com, this meant spending sometimes hours in a single night looking to find the right people to contact. It became ridiculously obsessive, and a huge waste of time. It also led to the next problem…

2. Like most men, I’m a relatively visual person when it comes to the attractiveness of the opposite sex. Many women on Match.com had as their primary profile photo themselves in bikinis and tight clothes. For the most part, I was able to resist clicking through to these profiles; clearly, their values didn’t match mine.

However, there were a number of occasions where I justified clicking through because I hoped that these attractive women might be more in line with my morals. 

I don’t remember having any kind of dialogue with any of these women. That’s probably a good thing.

3. I’m a clinical, analytical person. I used an insurance analogy in one discussion with my wife (then my fiancée) in discussing why I wanted to marry her. Online dating made me more clinical.

My first foray into online dating made me realize how clinical it can become.

Specifically, I found myself analyzing women in purely objective terms. I wasn’t objectifying, per se, but my mind was so used to assessing physical attractiveness via online dating for hundreds of profiles that it became something I did while walking down the street.

It was almost like I was at a horse show, looking at hooves and teeth. Except these were human beings.

4. Finally, first dates with women I met online were, for the most part, less enjoyable than normal first dates—because the “first dates” weren’t really first dates.

We had already sort of had our first dates via e-mail and phone, and therefore “first dates” were an awkward mix of first dates and final decisions. Things ended up being far more like a business transaction than even I preferred.

Sadly, at first, my CatholicMatch experience was lacking—but because I didn't know how to online date.

I ended up dating three women throughout 2012 before going to CatholicMatch in 2013. Despite the differences between CM and Match, I noticed some issues present in Match continued with CM. This was no fault of CM, but merely my own—had I not clicked through to those women’s profiles, had I not been so focused on “getting my money’s worth,” then merely going to a dating website would probably have not been problematic in the slightest.

But it was what it was. Just being on a dating website was apparently enough to cause issues. I left online dating shortly thereafter, and dated two more women over the following couple of years.

So I took a step back for a few years and then decided to try again.

The obvious question at this point is: Why did I come back to online dating in 2016? Frankly, I was just trying to put my toe back in the dating pool.

I was a few weeks past a hard break-up, when a woman I thought I was going to marry broke up with me. Online dating seemed to be a good way to slowly get back into dating “shape,” if you will. God’s plan was quite a different one—within a couple weeks, my wife looked at my profile. I e-mailed her, but figured that since she lived halfway across the country she’d never get back to me.

That led to six weeks of 90-minute daily conversations, and within six months our engagement. In retrospect, it was a human mistake to get into the dating “scene” so quickly after the break-up, but God took that error and made it a lot better.

My online/not-online dating experience is not much different than everyone else’s; it just has its own variations on flavor. The big thing I advise is to keep between the guardrails of the Catholic Church, letting its objective truths guide the subjective nature of your life.

Editor's Note: To avoid months or years  of making common online dating mistakes, check out our video course Matched: The Definitive Guide to Online Dating.