Tips for Taking Your Connection from Online to In-Person

So, you've met someone online.

You don’t want to move too fast, but you don’t want to drag the whole process out either. You want to take the initiative to meet the person who could be “the one”, but you don’t want to seem overanxious. How fast do you go in moving from an online connection to an offline connection? And how do you go about making the transition?

Every person is different and every relationship is unique, but everything can ultimately be compressed into three stages of online dating—messaging, video/phone-call, and finally to that in-person date.

When I was on CatholicMatch before finding my spouse, I started with a “three times” rule.

That is, after three exchanges, it was time to ask for a phone call or a Skype date. It didn’t take long for me to realize that the number of message exchanges was way too superficial of a benchmark to rely on.

You can communicate with some people, and three messages might not get you any further than just knowing some very basic biographical information about them—an extended profile, if you will. The messages can be mechanical, more about eliminating dealbreakers than really knowing someone better. To ask about a video date at this point can seem almost forced and jumping the gun.

On the other hand, if you’ve had three message exchanges and they have real depth and you get the feeling that there’s some genuine back-and-forth banter—the kind that says “I would at least be friends with this person if we knew each other in person”—then seeking a move to the next stage is appropriate.

These scenarios represent the opposite boundaries of the spectrum, and in-between there are any number of nuanced factors that can influence how you proceed. Is it a long-distance communication where travel isn’t immediately possible? If so, then a sharp limit on the number of messages can be counterproductive.

Conversely, if the person lives in your geographic area (let’s say within an hour or two, where an in-person date isn’t a major investment) then it’s worth moving a little quicker and finding out if there’s something there.

Keep in mind that life circumstances also play a role.

If you don’t have kids, but the person you’re talking to does...be patient. You have no idea what they may be going through in terms of extracurricular activities or anything else that might have them temporarily too busy to write a long message.

The biggest factor though, is your own well-being. Are you an imaginative person whose brain quickly develops deep scenarios about how a relationship with the person behind the message will unfold? This is often an idealizing of the other person, but it can work in the opposite direction too. Maybe there’s one or two things that remind you of an ex or someone else from your past and your red flag detector is on high alert.

Whatever it is, you can’t live with these kinds of mental images for too long. For the sake of your sanity, set some type of limit or benchmark. I ended up allowing my “three messages” principle evolve to where that was simply the point I assessed where the communication was at. If I wasn’t asking to move to the video/phone stage, I made sure I knew the reason why and that I was okay with it. And I thought a little deeper about what I did want to learn more about in the messaging process.

Once you're in the second stage, moving from Skype or the phone to an in-person date is a little less complex.

If you’re doing video, you can get a much better sense of what the chemistry might be like on an actual date. You know what the other person sounds like. What they look like on the video is how they’re going to look in person.

If you’re talking to someone near you, it may be tempting to skip this part and just arrange a face-to-face meeting. But talking to someone on your tablet or cell phone does allow you to do some very basic screening—are you going to be completely turned off by the sound of their voice, does their profile picture appear to be ten years old, etc? This interim stage can allow you to find that out without wasting the time it takes to drive and meet someone, then go through an awkward date.

This is a principle that I’ve violated, and there’s no failed relationship that I can attribute to a failure to do a phone/Skype screen. So I don’t want to overstate its importance. But the risk/reward factor definitely weighs in favor of including this middle stage.

Now if you’re long-distance, then video dating is almost essential. My wife and I had our first face-to-face encounter on Skype, with me in the Midwest and her in New England. By the time I got on the plane for the first face-to-face meeting, we knew a lot about each other and we knew how our in-person chemistry would function. She knew, for example, not to be rattled by a Midwestern accent as we walked around downtown Boston.

Moving from video to an in-person date should happen organically and take place as soon as circumstances allow.

Presuming that the connection you sensed during messaging was able to sustain in the first video or phone communication, there’s not much more to be gained by delaying the first date.

As you move through these early stages of connecting online with someone to meeting them in person, be sure to pray. There may be significant doubts that you’re struck with early on. While it’s possible they could be a sign from God and a red flag, it’s every bit as possible that it’s just fears and past wounds acting upon you. The devil thrives on ambiguity, which is there in abundance during the messaging stage of a relationship.

However, if you work through this early resistance, you can make it! Prayerful discernment and invoking St. Michael the Archangel will help you differentiate between what’s a real red flag and what is just the devil making noise.