Help! Why does he KEEP bringing this up?

Anonymous
Let's go way back in time, in high school I had a few male friends but I had one male friend whom I got along with really well, let’s call him Jack.

A random guy in one of my electives was making it really obvious he had a crush on me during my senior year. His friends were edging him along/teasing him and my girlfriends would often gossip about us as a couple. Jack took it on himself to be an absolute asshole to the guy. I mean seriously mean, like he went a little too far on multiple occasions. I ended up confronting him about it and he claimed his actions were justifiable because the guy was being creepy. I didn’t really know the guy who was crushing on me, and I never did get to know him (I suspect Jack's actions may have caused him to steer clear of me) so I moved on.

However that was 4 years ago, and Jack still brings it up to this day. Often he teases me about it, saying elective guy and I would have been a cute couple or that I did really like the guy back then but I was too shy to admit it (Once again, I didn't know the kid). I’ve asked Jack why he brings it up, he’ll usually sarcastically blame it on "trauma" from the situation and then goes back to teasing me about it. But, I kid you not, every conversation I have with Jack loops back to this same situation at some point or another.

I'm desperate for some insight into why he keeps bringing up the situation when it occurred so long ago, and why he's saying I would have been a good match for the guy when he clearly didn't like him. So, any thoughts?
Help! Why does he KEEP bringing this up?
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