"It'd be odd after all this time"
The longer the drawer's been shut, the harder the belief that opening it now would be strange. You've been married fourteen years and you don't say this sort of thing. Your dad is seventy-three and you've never once told him you admire anything about him, and if you started on Sunday he'd think you'd been to the doctor. Silence has set, and breaking it is now a bigger act than saying the good thing would ever have been.
I'll grant part of this. The first one after years is noticeable. Your partner will register that you said something you don't usually say. What I'd question is what they'll make of it, because the belief assumes they'll find it suspicious or strange, and I've given you two chapters of evidence that people find kind words warmer than the speaker expects. Noticeable isn't the same as odd. The first one is noticeable because it's rare, and rare good opinions are the most valuable kind, as chapter 7 said. Your dad won't think you've been to the doctor. He'll think you noticed him with the children.
There's a practical way round the size of the first one, which is not to make it big. Don't sit anyone down. Don't say "I've been meaning to tell you". Say the small true thing about today, in passing, and move on. "You were good with them this afternoon." Then talk about the football. The first said good thought after fourteen years should be the same size as the ones that'll follow it, because that's the point. It's not an announcement. It's a change in what you do with the thought on the stairs.
The same goes for the people you've drifted from, and here there's a related habit that an earlier book, Ring them first, deals with, which is waiting for other people to get in touch. If there's a friend you think well of and haven't spoken to in a year, the message that reopens it doesn't have to have news in it. "Saw a garden on Sunday and thought of yours" is a message, and it's a compliment, and it needs no reply beyond whatever comes. Dungan and colleagues' support messages, in chapter 8, were of this thinking-of-you kind, and they landed better than the senders expected.
Odd after all this time is a guess like the others. And the alternative to odd now is odd later, or never, and never is what the drawer has been quietly voting for all along.