It happened to me too; I downloaded this game in this version v0.3 for the first time, and did it all BUT I did wrong the ring thing, so I started over.
I've lost the chance to have sex with the doctor (or whatever that scene is) because I did the prank before going to tennis court, though.
But to the point, both plays I had that problem, Ann either didn't showed up or after that, didn't offered the sex scene after the prank.
Even when it says the prank can be done monday to thursday and saturdays, it only worked for me on saturdays, so if you wait until then or even better, just try to do it every day, she will eventually show up.
My advice, do the ring first, and then go to the tennis, and after that, the prank (talking about order, you can't do everything in a single day of course), or else you'll lose the chance to have whatever scene is with the doctor.
that's the best order, but this is what i do/did
get your massage up first, i say get it to 10, that's what i did
then do the ring
tennis on sunday, get the massage scene, by having high massage points, 10 but i think you can get the full scene with lower points, so you can get into the locker room and get the 2 scenes, women's locker room and then man's locker room, while in the men's locker room, you get the scene with the doctor, she will say something about when you come to see her for a longer scene
then do the prank when you go to milk with melinda, there are 2 different prank scenes, the one you want has the option to tell melinda to take you to the doctor, at the doctor's there is 2 options, get melinda to stay will lead to the doctor starting off with a handjob but melinda tell's her to stop, the other option is say nothing, this will lead to a full sex scene with the doctor
and for ann not showing up when doing the milking scene, i have know idea, i never had that problem, only time she stops showing up is when i gave her the white dress and melinda starts showing up in a new dress and hat, i also found out how to get suspicious points up, which i never found in an older version, so idk if it's new or not, so i keep on getting points, to see what happens, ended up getting 2 new scenes i haven't see before, 1 scene, she catch you looking at her ass with 2 options and the other scene she ask you about your love life with 2 options to pick from, so i'm still getting stuff to trigger, i also open up my save in save editor and saw mcboat = 0, so idk if thats for motorboat, if so, not sure how to trigger it, or if it's for something else or not in the game at all right now