Whatever you feel works just remember he's not [i]technically[/i] a guild member.
-laughs-
Could be fun for the three of them to fight together, might be more encouraging for hi to join. 
Or he could fight and in turn get his own ass protected by other guild members when he should have gotten hit and he kinda sorta learns the benefit of a team and a guild to look out for you.
Your choice it's your writing.
-nods-