I personally think that Arthur must have met Mary when they were both still teenagers, which might explain Mary's line when she says "we were so young" and they probably had a pretty long relationship or at least they tried to keep it up for a while, which might explain why Jamie gets along so well with Arthur and knows Bessie and Annabelle. I'm sure the picture Arthur and Mary took is of them in their 20's, and come on, pictures back then weren't as common as they are now, I'm sure they took that picture to celebrate their anniversary as a young couple rather than them being teenagers in love on a date.
However, Mr. Gilis probably got tired of his daughter hanging out with an outlaw for so long, especially if Mary had brought Jamie to meet the gang (since he had met Bessie and Annabelle). So he probably forced Mary to get together with Barry Linton (about whom not much is known, other than that he was a socialite like Mary), another possibility is that Mary decided to date with Barry Linton of her own free will, (since being an outlaw's girlfriend isn't easy, especially if he's in a gang as wanted as Arthur is with the Van der Linde), so maybe Mary was able to have a little fun with Barry while Arthur was away. (But I personally highly doubt that Mary was cheating to Arthur, I feel like that's not like her, so we'll take the first option.)
I feel that Mary, just like Arthur's priority is the gang, Mary's priority would be her family. So she, with a pain in her heart, would decide to marry Barry Linton (changing her last name from Gilis to Linton) and would write that letter to Arthur where she rejects his marriage proposal and tells him that now she will marry Barry Linton for the sake of her family.
And we already know how that ended, Arthur was completely devastated by that and also Mary left a bad impression on the gang after that, I think in this period Arthur must have been pretty bad (I've heard that he drank a lot and behaved badly with the rest of the gang even with Dutch and Hosea, but correct me if I'm wrong on this period.)
I think at this stage, where Arthur was heartbroken over Mary, he would decide (either consciously or due to the effects of alcohol or both knowing him) to sleep with prostitutes or have relationships with multiple women to try to forget about Mary (I feel like a younger Arthur in his 20's and late 20's would do that, and there are plenty of men in those ages who do the same); and I feel like Eliza, rather than being an ex-girlfriend of Arthur's, feels more like a one-night stand.
We don't really know anything about Eliza either, other than that she hooked up with Arthur and she had Isaac, and Arthur doesn't seem to have any feelings for her either. I mean, I know Mary was his first love and she was a big part of his life, but the fact that he didn't mention anything about his relationship with Eliza (other than that she was a waitress, they slept together, and nine months later Isaac was born) means that Arthur and Eliza were probably not even a couple; maybe Eliza liked Arthur and he accepted her, they had a fun night together, or they were just friends with benefits.
In any case, Eliza's pregnancy was something that wasn't planned, but I guess because of the affection she had for Arthur, she decided to have Isaac and knowing the outlaw life Arthur had, she decided to accept that and raise her son alone. And as we know, Arthur, upon finding out about that, decided to take care of them as best he could while he was still in the gang and we all know how that ended.
So to sum up, I have this order that I like to consider as my interpretation of Arthur's relationships (I've also seen that many fans share this interpretation) and I hope it helps you to understand things a little better.
Arthur and Mary met when they were teenagers, despite everything they loved each other and tried to make their relationship work (even though they were from opposite social classes), and they had a long-lasting relationship that lasted even when they were both in their 20's, and perhaps Mary out of love for Arthur was so confident with him that she took Jamie (who must still be a child) to meet the gang (hence why he met Bessie and Annabelle). And perhaps in this period they took that photo as a celebration of their anniversary and that's why Arthur keeps it so fondly.
Mr. Gilis got tired of his daughter's relationship with an outlaw, and he forced Mary to marry Barry Linton, making Mary reject Arthur's proposal and break up with him in a letter to marry Barry Linton. Arthur was devastated by this and in an attempt to forget about Mary, he slept with many women, among them was Eliza (who at least should have been his friend or friend with benefits) and that's how she got pregnant and had Isaac; and from there everything we know happens.
Some important notes are that here Arthur and Eliza could have an age gap, Eliza was 19 and here Arthur would be in his mid or late 20's (maybe between 24 and 28), which could explain Arthur's dialogue when he refers to Eliza "She did well, even though she was young", I know Arthur said that from his point of view at 36 years old; but I consider that if he sees Eliza like that, he should have been older than her by at least a few years than he was older than Mary. The important thing about all this, is that Arthur took responsibility and tried to help Eliza and Isaac the best he could, so I think in this case this age gap between Arthur and Eliza is acceptable. (I just hope Arthur was five or six years older than Eliza and not ten)
As for Abigail, I don't have a concrete answer, she probably heard about Mary because of the bad image she left in the whole gang (maybe Dutch, Hosea, Grimshaw, Tilly or even John himself could have told her about Mary). But you're right here, it doesn't make sense for Abigail to remember Mary, when she joined the gang long after Arthur was with Mary, and I highly doubt that Mary tried to visit or contact Arthur with letters in the 1890's (when they themselves say that they haven't seen each other for a long time).
So yes, you're right, we NEED a canon timeline for all of this, but I hope my interpretation helped you be clearer. By the way, I'm a big fan of yours, loved your blogs and your views! <3
prguitarman
origamiaround
