No it is not impossible. Get a highly skilled painter who knows what they are doing. It will involve a lot of sanding and filling the grain.

I'm not a lover of oak and can understand the desire to change it. But, I can also think of ways to update the feel of this room without painting the oak.

I'd paint the ceiling white. Place white painted board in the back of the shelves to reduce the amount of wood in the room. Change the tile on the fireplace. Bring in white rugs and furnishings.

The wood against the greenery out the window is lovely.

I think I would live with it a year and then decide.

I agree with kendrah, paint the ceiling (if choosing white please dont pick a stark one) get the curtains and furniture out , then reassess. the slate is one other area I’d consider changing before touching that wood. it will be a huge project to paint that all correctly.

" I don’t want to rip it all out, it’s 25 years old and has a lovely character to it "

Then do not paint it as that would be removing all the lovely character.

Ok, agreed on all of this and I love the idea of keeping it if I can bring it into this decade. I was considering painting the ceiling a moody colour, perhaps a deep grey or navy. I never considered changing the tile - great suggestion. What would you replace it with? And love the idea of changing the back of the awhile Ed.

Oops - typo. Love the idea of changing the back of the shelves.

It’s beautiful! Don’t mess with it. Paint the ceiling to brighten the room and get an interior decorator to help you modernize with furniture and decor.

Light colored ceiling, rug and furniture. I would choose less traditional chairs/furniture.

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Before doing anything else, I'd repaint the ceiling, remove the blinds, get rid of the rug, and see how it looks with your furniture.

@Dallas Fikowski id replace the slate with something not too busy. my preference would probably be a single piece of material covering the whole area, but i don't know how complicated that is with the wood trim already existing.

Once you paint the oak you can never go back. So do what you can to transform the space with the stained oak. If you still can't make it work and don't love it in a few years then reconsider. Yes to a moody blue-black or dark olive ceiling in here.

Do you intend to use the fireplace? If not, I'd try temporary peel and stick tiles to see what kind of color and vibe you want. I too don't know how easy it would be to replace the tiles.