I hadn't thought about it before, but on reflection, I do too. And I wouldn't be surprised if most people do.

Exaggerated a bit for effect, it would me more or less:

There = thehr

Their = thayr

They're = thay-r

"There" is just simple and straightforward with a pure short 'e' sound and no particular stresses.

"Their" has more of a long 'a' than a short 'e' sound, and a bit of stress on the vowel sound.

"They're" also has more of a long 'a' sound and it's pronounced just a fraction longer than in "their", and there's a very slight pause between the vowel sound and the 'r'.

Huh... learn something new every day.

I guess you're a native speaker. As a foreigner, I can only nod my head. We know.

They're/their/there are completely different words. They mean different things and they're pronounced ever so slightly different, and you'll get you hand chopped off by a centimeter ruler if you do it wrong.

"There" is clearly longer than "their".

"There" is one tone. "Their" is rising.

This is why I never understood the confusion with which spelling to use. Just say it in your head.

The most bizarre one for me is pronouncing the plural of woman as "wimmin." Can't explain it, can't work around it. It is what it is.

I wonder if it’s conditioned by word stress. “There” is usually the object of a phrase (and therefore stressed), while “their” usually modifies a following noun that gets the stress instead.

It's ther (or thehr, if that makes it easier to hear in your head) theyr and theyur

Seriously. There is a shorter word when pronounced, their has that sharp I/y sound, but cuts off right after the r. They're is pronounced with the they-are slurred like all contractions should be.

Atlantic Canada calling:

• There: Th-air
• Their: Thur

As a native english speaking, i tried to write the slight difference in the way i say them both (I didn't realise i said them differently until today) but I couldn't quite put it in writing so i deleted my comment 🤣

I had a friend from australia who pronounced every vowel of a word distinctly…. so consecutive vowels like ei or ea or ou, somehow she’d enunciate them distinctly.

How do you pronounce "they're"?

This is probably a regional thing. In Alberta I don't think I have ever heard someone say these differently.

There is a subtle difference for me. It's hard to describe and I am not a linguist, but it's like my mouth is a little bit tighter when I'm referring to the possessive their.

Maybe it's a US thing? I just tried it and I pronounce them exactly the same.