You should use the Naughty Tribute Mod.
I got all the pregnancies and if it says there is no hint to proceed further, that's when you go to the walthrough to see how many days you have to wait.
In the walthroug, it only says.
Having sex with Jenny provides the option of making her pregnant. One week later, read the phone message and enter her bedroom for the announcement.
It also says...
Do not make Jenny pregnant in order to progress further in her route.
So it doesn't happen the first time, regardless.
I'm not sure but it could happen after you do all this...
The Girlfriend Experience
Happy Meal
Watersport
Maybe by finishing her whole path, you can get her pregnant.
Also click on the cookie jar then the character and see if you have any missing scenes.
You should be good then. The impregnation mini-game comes up after you finished the last step in Jennys story as far as I know. The bug when the mini-game never came up was because they introduced a bug when converting an old save to 20.5.
You can also try
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. I think srksrk 68 fixed that bug with his mod.
srksrk 68 correct me if I'm wrong please with my ramblings. (Edit: already answered)
The mod god already took care of that. Install Naughty Tribute mod and you are good (I hope).
Thanks to all, the naughty tribute mod worked. But not in the way I may have expected.
I did a complete new reinstall in a different directory, copied my old save file over, and then installed the mod.
When I ran it, I still didn't get the pregnancy mini game, but I got a hint to buy Jenny the necklace at Cupid. So I went back to my original, unmodded install and bought the necklace. That was, it seems, the last necessary piece. After that, the mini-game popped up next time the MC banged Jenny, and she got preggers on the first try. Hooray!
The odd thing is this: I HAD ALREADY BOUGHT HER THE NECKLACE and given it to her. I remember for certain because (as I have mentioned) I hadn't played for several updates, and I had never seen that content before. Now, I've seen it twice. For some reason, I had to do it twice in order for it to trigger.
But whatever. Last remaining piece of the game is now complete for me. Every woman that can get pregnant by the MC has (a couple of them twice) and the babies have all been born. Done.