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Thanks for this, I should have clarified more. When I had posted this, I had completed all of the story and gotten full hearts for the main six. The Raylene sprite scenes not always working clears stuff up, as I only tried it like, twice? So I guess I just need to try a few more times.

I had already had Mary wear the adventuring costume, but when I went to do the "special job" at the bar, it just played out like normal. I had gotten a scene earlier once, before getting Mary's outfit, where Rose was sitting at the bar and talking to Raylene while the scene was going on, but nothing happened with Mary at all, even after completing all hearts and doing the scene at Midday.

If that clears anything up, I hope to receive some more tips, but I'll be trying it again with the recent 1.4.4 update as well.

Thanks for the reply!

Mary and Rose talking with Raylene while the main character performes his special job is also something that fires at random and won't happen every time.  I don't know the frequency but it's less then half the time.  You can check to see if the scenes are unlocked by seeing if they're available in the theater in the bunny mansion (you will have to pay to open up the theater).  Unfortunately, the theater does not have dialog so you have to see the actual scene for the full experience.

I also think that who shows up is time dependent but I'm not sure.  If you perform a special job in the afternoon then Mary might show up but if you perform the special job in the evening then Rose might show up.  At-least that's what I think.  I haven't bothered to figure out what the chances one of them show up is but I would say that it is less then half so if you perform the special job a few times then one of them will eventually show up.  If someone knows the actual chance they show up then that would be great.