For myself, I would find that a bit weird. I punt for my fantasy of that WG. If I was on holiday with that WG, then I'm with the reality of that WG. Fantasy and reality seldom mix well. I don't think I could handle the separation between the two, Attachment Syndrome comes to mind.
But everyone is different. To enjoy a holiday, I would have to enjoy the company of the person I am with. I have punted with some great WGs, but I'm not sure I could necessarily handle socialising with them. Sure they would play their part as they do on a punt, but the facade would inevitably slip over an extended period.
That's my ten penn'orth
NWG