Is he gauging my response

Hi so I'm seeing this guy and it's clear our feelings have deepened and that we have mutual feeings for one another. I think we are maybe both hesitant to make the first move towards seriousness so things are in a sort of limbo right now. I start a new job soon which means meeting new people and he said something along the lines of "going to find ya a new bf or something" and the other night I went out with friends and he playfully asked how many numbers I got. I can't tell if this is an insecurity about me possibly starting to date someone else (or even if I might currently be seeing other men besides him- I'm not btw). They seem like lighthearted comments but it's just a bit puzzling. Also to note he isn't the overly jealous or possessive type and I don't get that vibe from these comments