Caleb 100% does the silliest things to cheer up MC and has absolutely no shame about any of them
Even as a teenager, when other boys were too proud and insecure, he danced about the kitchen singing a song out of tune at the top of his lungs because his pipsqueak had a bad day at school
When MC was teased because she couldn't do makeup as a young teen, he practiced with her until she was good at it, letting himself be the guinea pig
He writes her notes and leave them around the house to cheer her up, usually with really bad little doodles that she doesn't have the heart to tell him are terrible (he knows, it's deliberate)
She fell in a puddle at the park just before her hs graduation and she was mortified because she put in such an effort to look good and now had to walk home covered in mud. Caleb doesn't hesitate and deliberately falls in afterwards so they're equally muddy together
He has a running joke, where he'd make more and more weird faces at her until she laughed - now, he only has to make one before she bursts out laughing no matter how down she is
Caleb's priority is always MC's wellbeing - he loves her so much, too much to bother about things like what people think of him when her opinion is all that matters ðŸ˜