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I'm glad it makes sense, and I'm happy to help. It's a great way of me understanding what I'm actually doing!
It takes a while to get the hang of balancing the aperture, shutter and flash.
It's covered in Strobist's 101 and the only answer is practice, lots and lots of practice. But thoughtful analytical practice.
Shame about the Tamron, I've heard good reports of it, and especially so of the similar sigma, but the 50 1.4 is very lovely too. Perhaps a little delicate, but I've heard the AF motor lasts longer if you keep the hood on it. It's a slight design flaw apparently.
A note or two on the new photo, I'll relate it to my scheme if you don't mind.
Relationship with subject, good. So it makes for a nice picture. Great start.
Lighting, this is where things get sticky. I'd prefer the background to be darker and the eyes to be a little brighter. More later.
Composition, this is the easiest to deal with.
The background isn't too good.
You need your background to complement and enhance your image if you're using something complex like this. You may find quicker success with plainer backgrounds.
The major issue is the horizontals skewering the head. Another problem is the bright patches in the background that are distracting. Don't sweat it, everyone has taken this shot
Exposure, It's not quite balanced between the subject and the background, but it's not so far out either. Lifting the exposure on the subject and dropping the background darker would change the image out of all recognition. It will improve
Focus, spot on.
So not too bad for what it is, and a step in the right direction.
Glad you went for the found light trip, night shoots like that are fun, but tough. You'll really enjoy it with an F1.4 lens
To get the best from your 380 you really, really need a sync cord. I have the 380 and early on I had no money at all.
I did have some ethernet cable, a screwdriver, lots of tape and a soldering iron though! The 380 will never sit on top of a camera again, but I can now use my TTL metering and HSS capable flash within 4 ft of my camera.
I'd reccomend buying a TTL cable, it will immediately help you get photos you didn't believe yourself capable of.
A small softbox or beauty dish will further enhance your photos in a way you will thouroughly enjoy
(My dish is DIY, it cost £4 and a bit of work with an angle grinder, some bolts, plastic film and an old CD. It was what I could afford. I still use it, my last shot of Mark was taken with it.)
Keep on shooting!