Certainly, she didn't mean any harm, but the woman has a tin ear. Least importantly, well adjusted guys don't usually want to think about their woman having been with other men (even though in most cases they know they have been.) So any "complement" that is predicated on her having, or having had in the past, sex with multiple other categories of men, is off to a poor start. More significantly, the "compliment" puts him solidly in what young men almost universally see as the loser category. "Nice guys finish last" has been folk wisdom since forever and "finishing last" is a synonym for loser! Women, if anything, believe the cliche more consistently than men. Every female fantasy one hears is for the bad boys. It is so predictable that men, in fact, rely on the principle, and pretend to be worse than they are as a mating strategy! What many men would hear when she says this is that he's in the category of "starter husband," i.e., the unthreatening guy young women marry, then kick to the curb when they mature into their full strength. Is he being too sensitive? That's one way to say it. But the other is, that he's being as sensitive as he is, which is the cliched weak position of exactly the kind of man he's being categorized as. So yeah, it stings more because her "compliment" strikes exactly where he already sees himself.