I was having a conversation with an ex-boyfriend about my dating life.
(…and yes, I did say ex-boyfriend, healthy people can realize they’re better off as friends than lovers.)
I was telling him about the men I’m currently crushing on; the little things I like, and the things that quietly irritate me.
For the many years my ex and I were together, I was the planner. He, on the other hand, was content with a quiet restaurant, sitting back and observing people, but when it came to romance; real connection, intentional moments, the kind that required depth, he showed up – fully.
“Babe, let’s hang out this weekend… where should we go? What should we do?” he would ask, and I, full of ideas, would always come up with something fun, something alive. It became our thing, it worked, we liked it.
So when I found myself saying, “I hate planning for dates,” even I paused.
“I feel unseen when a man is reluctant to make plans and I have to step in,” I admitted. “It makes me feel like I’m the one pushing for connection.”
The effort tells the truth
Then I asked him, genuinely curious, “Why didn’t this bother me when we were together?”
Was I dating wrong this time around? or was something simply… off?
Because there’s something unsettling about a man who wants your time but seems unbothered about taking initiative.
Maybe dating when you’re older is just more complex. Nothing feels as easy, or maybe, it actually is simple… and you just haven’t met your person yet.
“They’re not that into you,” the ex finally said. Simple. Direct. Slightly annoying.
But here’s the thing; this is a man who, despite letting me plan most of our dates, always picked up the bill, and when it truly mattered, he planned everything. Thoughtfully, intentionally and you could feel the effort. That was how he said, I see you. I care about you. I want to impress you.
So when he told me, “Most men won’t let you carry the weight of planning in the early stages if they’re genuinely interested,” I listened.
He went on, “A man who’s into you will be excited to see you. Even if it’s just over a walk, or a cup of coffee at a kibanda. He’ll show you something; effort, interest, intention.”
Now, I don’t know if my ex is completely right. He might be biased.
But when I sit with it… it makes sense.
So dear reader, here’s where I’ve landed: If your heart is whispering that you’re doing too much, you probably are.
Love, or even the beginning of it, should not feel like convincing, chasing, or carrying.
However… if you are initiating, and it’s met with equal energy, enthusiasm, and care, then girl, go on. Be open, enjoy it, let it unfold.
Because the difference is not in who plans, it’s in whether you feel chosen while it’s happening.