What’s it like getting it in deep stack vs deep stack?

I was playing 1/2 yesterday and was in for $300. After about 4/5 hours I had a stack of about $1,050 and there was another guy with a little over that amount across from me. I got into a few hands with him but never managed to get it all in with him. I was really entertaining the idea of trying to get it all in with him but the opportunity only came a few times and it wouldn’t have made sense to send $800 into a $100-$300 pot with him. Most of the hands I played with him heads-up, I was the winner. Maybe I should’ve tried just for the thrill because I’m not sure I’ve ever gotten it in when I’m deep stacked verses another deep stacked player. I feel like it must be super thrilling.