I don't have too much interaction with hockey players other than signing events. The Columbus Blue Jackets have held numerous signing events for fans, season ticket holders.. I used to frequent them with my parents a few years back (when I was 20-25 years old). We were at a time trying to get all the core/roster player to sign our CBJ flag. We've since really slacked the last 2-3 years in doing that.
Most players were super good with the fans, minus a couple exceptions.. James Wisniewski was a fan favorite for Columbus. Ryan Johansen was super cool when I asked him to sign the jersey I had of him when he was just entering his 2nd year in the NHL.
My dad has personally ran into/talked with Mark Letestu's dad, I believe at a bar in either Columbus or Nashville following a game.
My only "not-forced" interaction with hockey personnel... In mid december 2016 (Middle of the 16 game win streak) I took my girlfriend out to a nice dinner, a quick walk around the stadium, and picked up my tickets in roll call.. While waiting, I see Jarmo Kekalainen (GM of the Blue Jackets) talking with somebody- I think I'm the only person who recognized he was there. I turn to my girlfriend- "That's Jarmo Kekalainen"- Girlfriend- (politely) "Ok, who is he?". Explained that it's the GM/makes the hockey decisions with the Jackets. I then thought about trying to discreetly get a photo of him, my girlfriend even acted like I was taking a photo of her, but I never did. Didn't talk to him or anything.