YAY! You're doing some more writing!!! I'm delighted to see a new part of this story here.
Now we're beginning to get more glimpses into Clark's past, and it's fascinating. I do feel for him, especially given that his new partner, a woman he must want to impress, both professionally and personally (given that they've had a date!), is hearing all of this too.
And then the Kryptonite... aaarrrrgghhhh!
I have to say, though, that in a way this is beginning to feel like two stories in one. The first three parts or so were much more light-hearted and almost WAFFy in a way, despite the trouble with Lucy. Clark, in those sections, seemed pretty sure of himself and not really like a man with this kind of bleak past. It would almost make more sense if the date was a different story, and this, perhaps, was an Elseworld adaptation of GGGOH. Just a suggestion, which of course you're perfectly free to ignore - especially as you're only just managing to get back to writing this after a break. Don't get me wrong; I'm enjoying this very much anyway, but I wonder if you may actually have two separate stories here, rather than one.
I do hope you get time to write more soon!
Wendy