Why does a man talks about previous dates/hookups like he's talking about the weather?

Enlie
Hey there!

I'm finding myself in a little bit of a dilemma. I've met this guy a little while back and we enjoy spending time with each other, bunch in common, you name it... He is helpful, nice, kind and caring - even complimented me on several occasions. Also thinks about including me in his new work project, him wanting to hire me, blah blah blah.

We were spending an evening together, having a good time at my place when all of a sudden he starts bragging about going out last weekend and "almost" ending up sleeping with a friend he's known for years that he had a fling for back then. Grabbing a branch saying that he was too drunk to do it and ended up just sleeping beside her, hugging. A huge neon "WTF" popped up in my head then. I realized just then that it pinched me a bit, probably meaning that I have a little more than soft spot for him. I'm quite fine with that, but since I kinda thought that it was mutual, the "story" itself put my mood all the way down to my flip flops, not really knowing what to do nor where to go.

Is he showing off? Telling me that "there's no way in Hell we'll be together"? Or just plain insensitive?

Any advice would be greatly appreciated, thanks and take care everyone !
Why does a man talks about previous dates/hookups like he's talking about the weather?
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