A Tale of Two Men: An Online Dating Story

Two matches, two men… and two completely different approaches. Dun-dun-dun! 🤭

Ya’ll, I’ve been open about how I’ve been “dating” while traveling the U.S. as a nomad these past few months. I’ve also been open about sharing my various challenges and learnings with you all. So, here goes…

Recently, on a popular dating app, I matched with two fellows, K. and H., around my area. Both K. and H. showed interest. Thoughtful questions and conversations ensued. In each exchange, we uncovered things in common, and both of them asked about getting together in person.

A tale of two men: Exhibit K.

K. asked me about my plans for the week, so I offered up some availability. He replied, but did not suggest anything concrete. A few days went by, and I eventually said (during one of my more sassy moods), “I better not hold my breath for your plan-making, eh?” and he sent me his number and said, “You should text me. I don’t get notifications on this app.” I didn’t text him.

K. was creating unnecessary friction with this a self-imposed condition (which was almost self-sabotagey). We were already connected on this app, an app that had texting and calling capabilities. Why did he also need my cell phone number if we were otherwise connected?

I actually questioned K. on this stipulation after a bit more (app) messaging. He said, “Exchanging numbers is just more personal. Shows a greater commitment.” Commitment? That’s a bit premature. So was it control? Was it projection? He expected me to ‘prove myself’? I really don’t know. After a little more talk, K. never followed up to solidify something. It was unfortunate, because K. sounded like an interesting person based off our initial conversations.

A tale of two men: Exhibit H.

With H., it was easy. He didn’t project. Didn’t require. Didn’t expect or demand. Didn’t make it about him. Didn’t force anything. Didn’t follow the “script,” instead, he let it write itself.

When H. messaged to set something up, it went kind of like this: “I’m going to be in this city tomorrow. Do you want to do something?”
Me: “Sure, I’m doing this tomorrow, which is near there, why don’t you meet me?”

The day was refreshing and casual. No friction and nothing forced. And so, we met up a handful of other times. H.’s approach was on point. He was genuine, earnest, and completely chill.

⭐️ Maybe this was his regular style — building trust and making his dates feel comfortable. 

⭐️ Maybe he saw something in me — that I could be reserved and perhaps, even skittish — that I need to go at my own pace.

⭐️ Perhaps he sensed that me, or women like me — attractive, independent women, always on the move, with the highest of standards — would easily bolt if given the impression someone was only interested in external factors (appearance, money, power, status) vs. heart and mind — and turned off by demands.

I really don’t know which it was (or a combination). But it was an absolute pleasure getting to know H., friends-first. We had a lot of laughs, a lot of great food and wine, and he is an absolute treasure of a person.  

The moral of my online dating story

In a world where people want instant gratification, validation, and to do things fast rather than right, here’s my take:

ON RULES WITH NO MEANING OR VALUE: People, if you really want to get to know somebody (which is what we are here for, right?), don’t create arbitrary rules or friction. Take the path of least resistance. Why create additional hoops (with potentially negative interpretations) for someone to jump through so early, for no good reason, and give them a chance to refuse to deal with the drama? In other words, keep it simple, stupid.

ON PHYSICALITY: When a couple jumps the gun too fast on physicality, it can feel lust-driven or based on appearances, and not due to a true emotional connection, which needs to be fostered and built through multiple exposures. If one person is not there yet, it forces a premature ultimatum, IE) “I’m not there yet” becomes “I’m not there.” Or, the moment takes over, and it clouds judgment, and people are left backpeddling. It’s a mistake that’s made often, with sometimes disastrous consequences.

⭐️ In other words, when it comes to a high-value potential mate, don’t put up barriers. Don’t force. And don’t fast-forward. A natural progression is under-appreciated. 😘