The Nature of Safek Kiddushin: Ownership vs. Halachic Status

Rabbi Zweig opens by emphasizing the critical importance of developing strong Gemara (גמרא) skills—learning Rashi (רש"י) and Tosafos (תוספות) carefully, which opens up the entire world of Torah (תורה) learning. The shiur then turns to a case on Kiddushin daf 2 aleph: when a man gives money (natan hu) and the woman says "I am betrothed to you" (amra hi), the Gemara rules this is a safek kiddushin mid'rabanan. Rashi explains that natan hu resembles the Torah's phrase "ki yikach," while amra hi resembles "sikach ish al ishah." Because neither party's action alone completes the kiddushin formula, we are left uncertain whether the kiddushin worked. Rashi then shifts the discussion: if another man comes and gives her kiddushin, she requires a get from the second man, because we worry either the first kiddushin worked (in which case the second is invalid) or the first failed (in which case the second worked). But the Rav identifies a glaring difficulty: Rashi changes the facts on the table. The couple wanted to marry each other. The logical nafka minah (practical consequence) should be: how do they fix it? The answer should be simple: if you want to stay married, remarry properly. Indeed, Tosafos says exactly that: "im rotzeh, tzricha kiddushin acheirim"—if he wants to marry her, he must give new kiddushin. The Rambam (רמב"ם) in Perek Dalet, Hilchos Ishus states the same: "im rotzeh lichnos, chozer u'mekadesh." So why does Rashi focus on a second suitor instead of on the couple themselves continuing their desired marriage?