I had trouble finding paddling buddies when I moved back to inland PA from the Great Lakes (where I had started kayaking). I finally realized I would have to provide gear if I wanted companions so I bought a boat and gear to offer for a loaner, then added more and more boats until the last group I took out was me and 6 other kayakers, all in MY boats.
While having the fleet (all pretty nice boats and good paddles) did insure that I could regularly find folks to paddle with me for a time (day outings on our big and small rivers and lakes don’t require a LOT of experience or training), I eventually realized that I was just enabling my friends and family to avoid investing in their own kit. And it became increasingly burdensome for me to have to store and wrangle and load boats for others so I stopped arranging trips. I still share gear with a few nearby friends (who will help me load) but they are younger than me and still working so these are quite rare. Some others who I used to paddle with are my age or older – though they are retired, like me, they have increasing health issues and are no longer comfortable paddling.
So I had started looking for groups to join and that proved problematic because the majority of local group trips ended up being crowds of lily-dippers in rec boats who seemed to spend more time eating, regrouping and stopping ashore to pee than paddling. I did luck out and found a few fellow paddlers with touring kayaks who liked to do the distances and interesting locations I desired. But, alas, these local ones are younger than me and not yet retired. Also have significant others, kids and/or other obligations and little spare time, so are outings are few and far between.
I have learned that we female paddlers have some of the same issues with prospective “new partners” that the guys have reported: seems like every profile in personal ads lists “kayaking” as a favorite activity but this too often means that they rented a sit on top once (or just “thought about” paddling) and think stating this as a hobby makes them seem “adventurous” to the sort of women they might hope to sleep with.
I do have several people with whom I very much enjoy paddling (several whom I have met through this forum) but they live 10 hours or more drive away. I used to be a real road warrior and had no problem with solo drives of that duration, but now pushing 70 my stamina for such endurance trials is waning. Takes me a day or two to regain my physical and mental equilibrium when I reach my destination.
The perpetual problem: when you are young, vigorous and healthy you don’t have the money or spare time to pursue many of your passions. When you finally retire you have a lot of the latter, but far less of the former.
My last steady paramour was a handy kayak and canoe buddy who was well matched to me in fitness and trip ambitions, and we got out on the water a lot (he lived on 45 acres directly along a major riverbank, for one thing). But that was about all he was handy for, unfortunately. Honestly, as horrible a creep as he turned out to be in the end, I actually did stick it out with him far longer than I should have just because I always had a competent paddling, biking, hiking and road trip companion during the years we were together. And I knew that was going to be hard to replace, which has proven to be true.
I guess I am not offering anything constructive, just commiserating. If I figure out anything useful as far as lining up paddling buddies, I’ll let you know. All I can say is that having a second set (or more) of boat and gear to loan has probably worked the best for me.