Hi Kaybee, if you do enjoy this social circle, don't let him get you out of this. It's hard enough to meet a group of people you actually enjoy spending time with.
I had this problem for a while and me telling him in no uncertain terms to leave me alone worked, I did keep texts and if he would have bothered me, I would have had a talk with his parents (it's a couple of years ago and he is younger than me). Cops would have come after that.
Even if it seems harmless enough, something is not "mentally there 100%" and you never know if things might escalate some day.
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Blimey KB, your handbag must be huge.