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When two priest differ in their opinion on the same issue concerning a major decision in life (the choice of your partner in marriage), who do you believe; and who of the two is God speaking through? Can God say two different things to two different people concerning the same issue?

I wonder if the boy's confessor sees this relationship good for the boy and so encourages him; while in reality, it is not so beneficial to the girl. Do both priests know equally well the circumstances of the boy and the girl; or is each evaluating the situation from his own perspective?

I see that you are assuming this relationship is good and that God means for it to happen; while in reality, you should think that God had the two priests differ in opinion as a sign that it is not the best thing at the moment; but needs rethinking on both sides. Do not rush and blame the priests. They are an instrument in God's hands; for as St. Paul says, "And we know that all things work together for good to those who love God" (Rom 8:28).