After a bottle of wine...

[BEARFOOTSOUNDS]

Not bad, seriously. The intonation and style is pretty good. Sing with confidence!

I agree with the statements about "support", and the beginnings of phrases get a little muddled here and there. Enunciating while singing, and not sounding silly by over-enunciating, is a whole matter of taste. The classical-trained singers would have you sounding like a native-born Italian singing country, so, you know. A grain of salt.

As a practical exercise, perhaps finding some songs with longer tones will be of use to you, and that go into the mid-range like this song does. Or, just practicing some longer tones in general.

for instance, warming up with a major scale, and holding the top note, and then going back down. Maybe start in A or Bb, do the scale, then go up a half-tone until you reach a D or so. I have no doubt your voice can go quite a bit higher, but it's usually best to get a good, clear, not-strained high D before proceeding. (if going higher is even desired)

Cheers

 

[kickingtone]

BTW kingtone - here's the song I mentioned b4 that was composed to musically illustrate trip down a river
....

I got a sense of expanse, going back in time, revelation, solitude, followed by activity, before reading the full description, or looking at the words in the video. (There was also a "dancy" violin bit in the middle, that I didn't quite know what to make of ) I definitely got the sense of flowing water, too, but you'd already explained that. So, as you said, the music doesn't only fit, it actually tells the story.

 

[kickingtone]

Oh...and something crossed my mind...

Some foods/drinks can dry out your vocal chords, slightly, affecting your singing. Anything containing alcohol is a good candidate, but there are a host of other things, all depending on the individual, of course. (Even the weather or room/studio humidity can have such an effect). So, it's a good idea to keep tabs on what you eat/drink/weather, so that you know when it is optimal to sing.

All the best impressing that girl, btw. My guess is that she's made up her mind before you even touch that guitar. Just make sure she thinks its more about her, or you and her, than about you! That's the trick, isn't it?
If she's into you, she'll find a way to like it... ...until you overdo it. Not really a problem, unless it's a long term thing, by which time... make sure you've nailed a few of her favourites.