A risk with your heart and a risk with your money both deserve thinking. Only one usually deserves a spreadsheet.

Both of these deserve real thought, but not the same kind. Money risks have numbers in them: a price, a downside, a length of time to recover. Feelings do not come with figures, and importing figures into them produces confident nonsense, because you end up optimising something you cannot actually measure. Thinking carefully and calculating are two different activities, and mixing them up ruins both.

For the money one, write the cost, the worst case, and how long it takes to recover. For the other, ask instead who you become around this person and how you want to be treated.