You want the the truth right? Or do you just want a reply that will feel good? The truth as I would give it to a friend. To me it sounds like this individual is just a really damned nice person who obviously considers you a close friend and colleague (at a minimum) but also has some issues with boundaries and being able to put themselves in others emotional shoes to view their social interactions from a bigger perspective outside of just their own. And I don't doubt this person is great as you've described, but maybe they are lacking in EQ (Emotional Intelligence basically). Another thing, lol, this guy can stay away from his chic and text her all the lovey lovey stuff he wants if its working for him lol. Clearly you have different relationship "norms" and aren't overly verbose in the public forum to your partners as your friend is with his... no biggie though. There is no right or wrong. You already respect the guy, respect that he's running his personal life competently and maybe you're just a tad jelly:) As for how to broach the whole attraction topic with him.... totally out of my ballpark. I just have a feeling he's more committed to his girl and job than even you may realize. Don't get hurt and lose the professional connection... go find you a single man friend. Best of luck