#1
Hey so I realized recently that during my improv solos I often find that I keep bending on the same scale degrees regardless of the key that I am soloing in. I find that I consistently do a full bend from the 2nd scale degree to the third scale degree or I do a full bend from the 5th scale degree to the 6th. I recognize that the underlying chord is very important for this question, and I usually try to do the bends that I talked about when it fits the chord. However, often when i try to do other bends like from the 1st to the 2nd in say the V chord, it just doesn't sound nearly as good as the two bends I mentioned earlier. Any advice or am I just crazy?
#2
Generally speaking, these notes tend to harmonically lead into each other. 2->3 implies a neighbour tone (ie. they're a half-step a way), while 5->6 implies the tonicization of the relative minor. 1->2 over a V would be a bit awkward because the 2nd resolves to the tonic in a V chord.

A way to get around this is to use these consonant phrases as a framework, and fill in the spaces with dissonance to create some excitement. That or change the chords to better fit what it is you want to play. I personally like to fit 1->2->3 with I-vii->I6....
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#3
Bend as you see fit, I've never seen it as one of those things that needs to be broken down.

Keep in mine that bending is an articulation not a note choice - if you played those same notes not as bends but instead as two fretted notes they would most likely still not feel all that great to you as the notes you normally bend.
#4
A bend is just one way to move between two notes, that's all - if you want the sound of a bend when you move between two notes then use one.
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#5
Well, I can't really give you advice except to say you're doin' it right. By listening and figuring out what sounds you like, and then figuring out how to get those sounds in different keys, you really develop your ability to sound good.

I'd suggest you try bending to the third of each chord as well as the root and fifth, thirds tend to be a little more flavourful than the rather plain root n fifth.