After being promised the King's oldest daughter, Merab, only to see her given to another man, David finds himself deeply disillusioned. When King Saul attempts to offer his second daughter, Michal, in marriage, he is forced to use indirect methods to convince the young warrior. David deliberately avoids responding to the new proposal. He fears that the King is either mocking him again or simply offering empty words of encouragement without any real intention of following through [מצודת דוד, ביאור שטיינזלץ]. Having already watched his promised bride marry someone else, David has completely lost faith in the King's guarantees [מלבי״ם].
To bypass this wall of distrust, Saul commands his servants to speak with David secretly and quietly [מצודת ציון, רד״ק, ביאור שטיינזלץ]. This covert approach is a calculated move designed to lend credibility to the King's words. By having the servants approach him unofficially, Saul hopes David will feel the offer is sincere and genuine, rather than another lie or cruel joke [רד״ק].
The servants are tasked with delivering a reassuring message: the King truly wants him as a son-in-law, and the royal staff deeply admires him. Their goal is to ease David's fears by explaining the previous failure. They tell him that Merab's marriage to another man was not the result of the King changing his mind, nor was it caused by jealousy among the royal servants. Rather, they claim that Merab simply rejected him of her own accord. Now, however, because Michal genuinely loves him, he is presented with a proper and real opportunity to marry into the royal family [מלבי״ם, מצודת דוד, ביאור שטיינזלץ].
Adding another layer to this complex family drama, an ancient tradition offers a different view of how events unfolded with Saul's two daughters. According to this perspective, David actually did betroth Merab, but the union was based on a mistaken legal premise, or her subsequent marriage to another man was done in sin. Following this account, David only married Michal legally after Merab passed away [רד״ק].