I morely play with inflatable toys than balloons, but still, I do feel sad when they pop, yeah.
Mainly because it always happens at the least expected time. Plus I try not pop my inflatables, so it makes me sad when one of the ones I really like pops underneath me.
I had this big inflatable pony from some old plug-in TV game (I only ever bought the inflatable pony part, not the plug-in game it came with), and I really liked it because it was such a big inflatable, and so cute. One day, I got it nice and inflated, straddled it, and BOOM! It popped.
It hadn't overinflated it, and I had been playing with it for months. I guess all the times I rode it down as it deflated just wore out the seams. But yeah, I was pretty sad about that one.
Same for when my first Intex Gecko (I bought a second one later on), my Intex Happy Dino, my first Jet Creations Baby Tiger (I bought a second one later on), my Banzai Pink Seahorse, and my Digimon Agumon (Ivhave no idea what company made it) all popped.