The Squire of Dames of pretty much the ultimate ladies' man, and in Spenser's Faerie Queene, that's not really a good thing. While the Squire isn't malicious, he is foolish, becoming the object of ridicule when his own skills of seduction backfire. His lady first instructs him to prove his love to her by sleeping with a many women as he can in a year (go figure...).
Well, he sleeps with 300. So then she gives him another challenge: he needs to find just as many who won't sleep with him. And in this department, he's having some serious problems. His ridiculous "quest" is a parody of chivalric behavior (see Chivalry in Symbols, Imagery, Allegory) and acts a foil to the many good knights in the poem who are loyal to only one woman (who doesn't make them fulfill bizarre and impossible tasks).
But since Spenser keeps a pretty light and fun tone throughout his descriptions of the Squire of Dames, it's safe to say that while there's definitely a moral lesson here (spoiler: there always is with ol' Spense), Spenser is also just having some fun.