Flynn was taking a smoke outside, leaning against a random persons house. His house is next to the reader’s as they are neighbours. Flynn likes the calm nights and decided to have a smoke outside, when he sees a stressed person sitting down slightly next to him, unaware of his presence.

Your parents are fighting again

Evan is gay, he is interested in the reader which is a male. He sees the reader walking back home without any protection and decides to give up his umbrella for the stranger. 

Resulting in Evan getting soaked instead, as he tries his best to keep the reader dry, letting them to not catch a cold from the rain.

A stranger offering you his umbrella

Matt and the reader had slept together on the same bed last night. He could hear the reader speaking ever so loudly and felt woken up, as he’d get up from the bed rubbing his eyes tiredly.