Shear & Sheer

Tort & Torte

Our lawyer dude is back again, this time with some sort of legal injunction against the deliciousness of Thanksgiving! That does it, he's not invited back.

Root & Route

Root – (n.) The portion of a plant that anchors it to its surroundings and absorbs nutrients. (v.) Cheer.
Route – (n.) Path, direction.
Why do carrot farmers get lost in beet fields? Because they can't find their root.
...Meh, that joke sorta works.

Close & Clothes

I suppose, technically, these two words aren't supposed to be pronounced the same. But where I come from, they most certainly are.

Currant & Current

With an A – a type of berry.
With an E – (n) a flow of water or electricity. (adj.) belonging to the present time.

Soar & Sore

As in, "Can a bird soar if its wings are sore?"

Flocks & Phlox

Birds travel in flocks. Bees travel in phlox.

Hall & Haul

Gait & Gate

Gait – a style or manner of walking.
Gate – an opening or doorway in a fence.

Coarse & Course

I told you last week's map would show up again...

Cite, Sight, Site

Getting tired of seeing that book yet? :) Just wait till I start reusing the map!

Addition & Edition

I ran across a really rare math textbook recently. It was a first addition.
Yuk yuk yuk.

Hart & Heart

Hart is a pretty obsolete word for a stag, so I almost didn't do this one. But since I already had the deer drawn, there was really no reason NOT to include it.

Hostel & Hostile

Yes, I'm aware that Hostile can be pronounced with the long I sound instead, if you prefer. Either way, I think we all know who ends up with top bunk here.

Lean & Lien

Our legal friend is back, apparently with some kind of claim against the leaning tower of Pisa. Good luck with that. I don't think this is the last we'll see of him, though.
(edit 8/29/15) Looks like I forgot to include the description of Lean as in "thin." I suppose the fact that the tower is a pretty thin building will have to suffice. Works for me.

Manner & Manor

Chile, Chili, Chilly

OK, I'm not trying to be misleading here, but this – like most things – is complicated. Chile, with an E, is what we call a hot pepper. That's the only definition for that spelling. However, chile is an alternate spelling of chili, with an I, which can mean the same thing. But chili with an I is also what we call the meat/beans meal often made with chiles. Make sense? To sum up:
Chile always means pepper.
The meal is always spelled chili.
Chili can also mean pepper. (That's why I decorated the bowl with chilis in the pic.)
Chilly, y'know, just means cold.
And Chile is a country in South America, which I'm not including here because I don't do proper nouns, and half the people I know pronounce it CHEE-lay anyway.

For, Fore, Four

HW's 250th post! Just for you. Fantastic.

Gorilla & Guerilla

My all-time favorite homophone! I remember giggling about this in junior high with my friend Abe so much that we got in trouble with a librarian. :)
I suppose, looking back, it's not that funny, really. It's also a lazy anglicization of a Spanish word, so you could make the argument that these really aren't homophones at all. If you wanted to be that way.

Tortuous & Torturous

These two are NOT homophones. But they're also NOT THE SAME WORD! That second R makes quite a difference, people. I'll admit that solving a maze might feel like torture, but the route through a maze is not Torturous, it's Tortuous – winding, circuitous, complicated.