Outlaws of Love:
I think it's a song Jon wrote somewhere between 1989 and 1991. I'm with you Dominik, that the first verse fits his situation with Dorothea at that time perfectly.
But I think that the demo happened with the band for Keep The Faith. Although the song itself would fit into the 80s, the band's play doesn't.
The muffled guitar riff sounds a bit like the beginning of I Believe where Richie does some kind of muffled slide, too, before he starts the dirty riff.
The line "These days you're two paychecks away" was used again in Hey God. So I think it's not too far fetched to say it's been worked on and recorded during KTF but it didn't make the record and while writing for These Days that specific line stayed in mind and was used again.

Getting back to that point: Jon's memory is always about the last instance to use when it comes to entering a certain timeline. He couldn't remember in 2008 whether Open All Night was from Crush or Bounce (even though he praised the song for its lyrical content in the WWWB documentary, so it must be an important one for him) and on the Borgata concert for the Box Set he couldn't even pinpoint when Radio had been written. After the song he mumbled something about it being from the New Jersey era with Richie intervening and correcting him that it was from the KTF sessions.

Later on today or tomorrow... I'm going to revise the final list and make it nice and organized... if anyone was additional comments or facts that need to be included, just post them and I'll update it...

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I just read the lyrics and this is not about Dorothea or the Grey Summer... It's a fictional story about a couple that got married too young and are having issues because of it... however they are just soooo in love blah blah blah...

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I remember watching some vid with Jon who said something about being with Dot and that she was brave because he had no school, no money and just waiting for his luck but she sticked around. The lyrics may be as well about him and Dorothea.

The story is most likely fictional, but we just said that the first verse/chorus could've very much been inspired by Jon's and Dorothea's story.

To be fair we don't know if it's a Grey Summer song but if it was written 91ish or KTF that would indeed make it a GS era song. We can romanticize a time period all we want, it doesn't take the timelines away if we don't like a song.

So I finished up to These Days / Crossroads... The inserted years are from Obie's list that was attached a few posts up. Most are pretty consistent so far with the exception of 2...

The First Inside and Why Aren't You Dead - The DVD stated KTF but Obie's list has 1994 noted.

I'm going to finish DA Sex Sells and Crush tomorrow.

I also removed Prayer, Always, Sat Night and couple other obvious ones...

Two things:

1. If a couple of those were in fact written with Eric Bazilian (is that acutally listed somewhere?), then couldn't it be that they were pulled because of that story with Jon/Eric an Ugly? (i.e. maybe Eric didn't want the songs to be released and hence they wrote new ones?)

2. Wasn't there some sort of "track list" from the KTF sessions? I can't seem to find it, and maybe it was from a different album, but I think it was from KTF and there were a lot of songs on it, maybe even Outlaws Of Love, but I really can't say...

#2....That's Right!!!! It was hand written!!! Brilliant!!! Someone needs to find it

#1....The only story I know about Ugly is that Jon basically stole it and just changed up the style. But I thought Eric was cool with it so I'm not too sure I get the point...