You just have to make it a place he wants to go. If you use it for punishment then he'll not want to go in because it's then not a fun place. If it's a place he gets toys and treats he might go willingly. Also can try to teach the cue word of kennel. Maybe by throwing pieces of chicken in and when he goes in say "kennel" without shutting the door and eventually shutting it and intermittently treating him to teach he goes in, treat or not.
With how much he loves attention and to be with people it might not work out, but you can try it.