Some men drool over the latest issue of Hustler. If packing wheel bearings Tweaks His Beakie, it's a cheap endeavor. Personally, I find visiting friends who use a television remote control like a veteran telegraph key puncher who stutters to be irritating.
Seriously, he may be the "worrier" type. Like a driver who periodically taps a brake pedal on a empty flat highway or checks a rear view mirror on a multi-lane highway when he has no intention of changing lanes. I've left new pencils on my desk and three days later found them on someone else's desk amidst a dozen other long pencils that look like a rat has had-at-the-eraser.
Hope this made you smile. At least you know the trailer bearings and brakes are well maintained.