James: 'If I Could Tell Her' - I know the context doesn't work, but it kind of feels like him and Lily

Sirius: 'To Break in a Glove' - he didn't have great parents, and it's canon that Mr. And Mrs. Potter kind of took him in

(Also Sirius and James would totally vibe with 'Sincerely Me')

Remus: 'Waving Through A Window' - he always felt separate from everyone because of his lycanthropy

Peter: 'Good For You' - kind of directed at him, he got the friend group he wanted, but then he betrayed them