Continuing from yesterday, I think I'd arrange the game in cycles. Like, each cycle has a segment where our hero has a priest-in-training challenge, a segment with love interest 1, a segment with love interest 2 and a segment with love interest 3. That cycle repeats three times, at which point the game ends. If I decide to keep Nasty Old Lady as a character, she could also have a segment every cycle.
Priest-in-training segments will include writing a homily, surviving a parish council meeting, preparing an RCIA lecture, a confirmation retreat with surly teenagers, impressing the vocations director, and a diocese-wide priest meeting. Maybe I'll have 1-2 of these per cycle.
If I write the game this way, each love interest has three segments before the end. That should be enough time to start and finish a storyline, right? I know another standard way to do it is to have two cycles with each love interest, then you pick one to pursue in-depth, while the others fade into the background.
The next step for this game would coming up with a three-chapter storyline for each love interest, and making a full outline from there.