I have some comments on Theodora's sexual history.
In the current version, the first sex takes place on the living room table. As we understand from the dialogue that follows, whether she ovulated that day or not, she took the morning pill and is therefore not pregnant. The next sex in the living room takes place with a condom. But the MC has the opportunity to have sex with her in the shower without a condom. And immediately, a unique event occurs involving the purchase of a car and the subsequent time spent with her, which is almost the only opportunity to impregnate her. Subsequent events in the shower don't offer such a serious chance. (And supposedly, if she takes the morning pill every time, after having sex like that, there will be no opportunity to impregnate her).
I think it's too difficult to get further development without knowing this subtlety. In this regard, it would be logical to make the unique event of buying a car triggerable. You need to have either the first sex and at least one shower sex during her ovulation, or have sex with her in the shower a couple of times during ovulation (a recurring event). Then you need to make calling Theodora on the day of her ovulation trigger an almost linear event with shower sex, buying a car, ending with her getting pregnant, and opening up other events.