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?