Tell him there are plenty of jobs in the armed forces.

It sounds like he's in a funk, and sometimes when you're in a funk you damn well want to stay there! So first of all, recognize that you can't help someone who doesn't want to be helped. Sometimes, just being available to hang out and maintaining a non-judgmental, supportive attitude is the best you can do: allow him to come to himself on his own time. But, on the other hand, maybe he needs a right slap in the face to bring him to his senses! Or, perhaps some well-directed, gentle nudging would do the trick? To be honest, I'm surprised he can't find a job. Obviously I don't know the market where you live ... but then if the market is the problem, he might consider moving, because tending bar is usually a fairly easy job to get, especially if you have training. Maybe you live in a small town? There's nothing like big cities for the service industry and for alcohol consumption! If you're interested in either the slap or nudge method, you should ask yourself: "Why can't he find a job?" Because if, as I suspect, the market isn't the problem, that means he isn't approaching his job search in a useful way: i.e. he's got a roadblock up that he himself is able to take down, if only he could see that it's there. Maybe his expectations are too high? Is he only applying to the coolest bars? Is he rejecting bar-back and other subordinate positions? Even with training, most people have to work their way up in their careers: if he's setting his sights too high, he won't get anywhere. Maybe he doesn't look the part? Sometimes a simple make-over does the trick. (This could mean a physical make-over or an attitude adjustment.) Maybe his resume doesn't look the part? Did he consult any resources when he designed his resume? He might consider asking people in the industry what his resume should look like and what information it should impart; as well as consulting more general online sources. Maybe he's not looking in the right places? Bars and restaurants generally don't advertise their positions: they don't have to because they can rely on word of mouth and on walk-ins. If he wants to tend bar, he better hit the pavement first, and start networking second. Print and online sources should be his third place to look for work. When it comes to hitting the pavement, it REALLY helps to take a map of the city and carve it up into day-sized chunks: every day, hit a different chunk, and hand in resumes to every place you see there. That way, nothing is missed and because you have a plan you don't end up drowning in hopelessness: at the end of the day even if you have no job offers you go home feeling productive because you know you've accomplished what you set out to do.