The game features three different Paths that split off at the end of Week 3: the Romance path, the Political path, and the Observation path.
To get on the romance path, you must successfully win the heart of one or more of the Approved Romances. Then, during the third and final matchmaker interview, you have to tell the matchmaker you choose a love match, choose the desired love interest (assuming their path has been unlocked), and confirm your genuine affection for them. Love matches are not for marriages of convenience. Those can be arranged through the Political path (see below).
SPOILERS BEYOND THIS POINT:
Ana's romance path is unlocked by default at the beginning of the Welcome Feast. To stay on her path, attend her Week 1 training invitation, and invite her to a private meeting at the beginning of Week 3 .
Impress Clarmont at the Welcome Feast by rescuing Penelope from Jarrod (requires 50 Courage, 200 Likeability, 85 Academics, or 75 Manipulation). Attend his Week 1 dinner invitation and seek him out in the gardens in Week 2. You will only pass his week 1 event if you are Ethical or else have 75 Manipulation.
There is no special trick to unlocking Emmett's path. Speak to him at the Welcome Feast, attend his Week 1 nature walk invitation, and wait for his Week 2 event to auto-fire. It may be possible to unlock his romance even without doing his week 1 event, if you get his social stats up high enough by other means.
Lisle's path is difficult to unlock as it requires a very high friendship value with both him and Penelope. It's impossible to select him as an option with the matchmaker in week 3 without succeeding at his week 3 event.
Lyon's romance will only be unlocked if you pick very specific dialogue options during the Welcome Feast conversation with him. Passing his week 1 event requires at least 50 Intelligence, as well as being Ethical, Noble and Compassionate (or at least not selfish and indifferent - it's impossible to be perfectly neutral on the ethical/immoral scale). See Lyon/Romance Walkthrough.
The Political path revolves around arranging a favorable match for your MC and getting it approved by the relevant factions. It's possible to be on the Political path and pursue an unapproved or secret romance, although not all desired matches are likely to accept this. Not much is known about political matches, because this path does not begin until after the demo content.
There are several secret romances that can be pursued while seeking out a beneficial alliance. These are mostly relationships where marriage is not an option (Gisette, Ria, Woodly). In one case, marriage is an option but the Matchmaker refuses to give her blessing. Gameplay-wise, this fourth romance functions exactly like the other three.
Get on the Observation path by telling the Matchmaker you're not interested in either love or marriage. Jasper has Feelings about this, which he may share with your MC before or after the last Matchmaker interview.
Most observation content appears after the end of the demo.
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