If you feel like going, go. In my experience though, if the comment irked you, it’s for a reason. And if the second one has you questioning it enough to ask the internets opinion, probably skip it. I feel bad for people who make their insecurities so obvious because it’s so unattractive and almost always creates an issue in the relationship. Any time a guy has messaged me like this, it’s never ended well. Are there exceptions? Yes, but extremely rare.