I was discussing this with my fiance, and she agreed with me in that she also speaks English in this manner.
I have found that, at least personally, I tend to speak several common homonyms in English in distinct ways: bear/bare, they're/there, where/ware. It's difficult to describe the differences in a concise way, but I'll do my best, and maybe use IPA where applicable, assuming I'm not using them incorrectly?
The traditional pronunciation of bare is [ˈbɛr]. I would completely agree with this, and while the dictionary might also say bear is pronounced this way, I would argue that I often hear it more as [ˈber] — a more closed sound with the lips pulled back in a smile. Sure, sometimes people will lazily say both in the same manner, but if I say [ˈber], the listener is going to recognize in a vacuum that I am speaking of the furry mammal, not the term to describe a naked person.
Similarly, there is rendered as [ðɚ]. There is a perfect rhyme with bare. I agree with this. However, they're is given the treatment of being a contraction of "they are", and it similarly has that closed sounded [e] instead of [ə].
Am I crazy, or does anyone else out there experience English this way?
I'm kind of uninformed about English ongoing changes, specially when it comes to NA dialects, so I hope that another poster chimes in.
That said, your description immediately reminds me two things.
One of them is /æ/ raising, a similar phenomenon affecting /æ/. Specially relevant here because /æ/ is right next to /ɛ/, raising /æ/ would leak it into /ɛ/ territory, and your description of how you pronounce bear hints that you're raising it. (Or alternatively you're lowering bare).
The second one would be the Northern Cities Vowel Shift, that likely applies to you, based on region. Usually the shift wouldn't apply to vowels before /ɹ/ (except /ɑ/), but perhaps this exception is going away.
Note that this type of sound change can actually split former homophones, specially verb vs. noun vs. adjective, given different stress patterns. For example, for plenty Australians the verb can (e.g. "you can do it!") is realised as [kʰæn]~[kʰɛn], while the noun can (e.g. "a can of beer") is [kʰæ:n]~[kʰɛ:n], with a longer vowel. While this specific split likely doesn't apply to you, the underlying mechanism might be the same.
Just for curiosity, how do you pronounce the verb "bear", as in "bear with me"? Is it homophone with "bare" or the animal?
I don't know anything about linguistics and can't add anything of value, but Northern Cities Vowel Shift is a great band name.
Wow, what an illuminating read! I would totally agree that the differences in tension are what create a majority of the pronunciation difference, as well as the slight raising of the vowel.
"Bear with me" is definitely homophonic with "Bare". The "bær" is an animal, specifically, and I would say that all uses of the verb I can conjure are the more relaxed "ber".
Going through this website has been fun. https://www.thoughtco.com/homonyms-homophones-and-homographs-a-b-1692660
Do people really pronounce most of these the same??
That hints that you, your fiancée and others speaking the same variety are raising the vowel only in nouns, as nouns usually get a stronger prosodic stress. So it's a lot like the Aussie can/can split that I mentioned, except with another vowel.
I'm not sure but I think that they're listing homophones across multiple dialects spoken in USA. As such, for any given dialect, only some of those would apply. (It's for USA only for sure - note how there's no pair like more/maw or pander/panda).
Actually I feel like "can" is split here locally, too. "I can do it" comes out mostly like "k'n", it's highly reduced and closed. "A can of beans" is open, stressed. I guess it's a general feature of prosodic stress. I gotta read more about that
A bit of reduction is normal, since English relies heavily on the stress for the prosody. And by your description ("highly reduced and closed") you're likely realising it as [ə] or similar.
From what I've seen for your general area it isn't usually phonemic; the nearest of an /æ/ split would be Philadelphia and New York. Exceptions do happen though, and what I'm saying relies on studies from Labov from half a century ago.
A good way to test this out is to pretend that someone asked you to repeat the word, so you emphasise it, like:
If it's phonemic for you, even under emphasis you'll pronounce them differently.
Regarding your second link, I've been told before that our region has a distinct influence with northern Great Lakes English. I can go to Wisconsin or the UP and hear almost a "magnified" version of what I do accent-wise, but I guess I never really picked up on it being its own dialect, though of course it must be. Southern Hoosiers have such a different accent from us, it's very funny to hear the comparison.
It's really common for borders between dialects (and languages, too!) to not coincide with any sort of political border. And to make it even messier, sometimes there's no border to begin with, only gradual transitions - and I think that's the case here.
Based on this map your dialect would be probably Midland English, but you live so close to the Great Lakes English-speaking region that you're actually speaking a transitional dialect.
Looking the map over, I am actually in the Fort Wayne/South Bend region and it appears that this is transitional began Midland and Great Lakes.
Thinking about it, it may also be useful to note that there is a strong Pennsylvanian Dutch influence in my area given a large Amish population. I do not speak it but I can't imagine that there hasn't been at least a little bleed into the English here.