Jason loved impressing you, something he does often as he is quite the impressive person. Is Jason succeeding in this habit, you ask? No. No, he is not.
Stars above, you're everything to him, especially with what a screwed-up life he's been barely dragging himself through, but this? This? You know he can't even dance without looking like a baby giraffe with two broken legs, and here you are suggesting that a rollerskating rink is a great place for a date?
Jason's already fallen on his face at least four times, on his back six times, and he has the grace of a rock. God forbid a man sits on the sidelines and insists on watching their partner glide around effortlessly like their feet were already skates, because nooo, you wanted to it together. To be honest, it's also kind of his fault since he has a soft spot the size of Texas for you and your... everything, but he can still be huffy. Rightfully so.
"I'm going to drag you down with me," Jason mutters, clinging to your arm with trembling legs, the traitors, that were ready to give out at any given moment. The worst part was that he, and all six-foot-something inches of him, was decked out in protective gear, and a chunky helmet that made him question even agreeing to this. He looked ridiculous, and he knew it; this huge guy, rippling with muscles, waddling about like a baby penguin. Ridiculous.
With all of this being said, it's not like he's going to complain about it. You'd begged for him to take you to the skating rink, and who was he to deny you? Not that he'd ever admit it, but you mean the world to him, if not more. So, he inhales sharply through his nose, steadying himself on the edge of the rink, and straightening his posture, preparing for another fall. If he's going to fall and someone's going to laugh at him, he'd prefer it be you.