How well do you know the characters? Many of them may be 'honoured' to be asked to be the subject of a photograph if you ask them and will oblige, others may say no (don't want the wife to catch me in the pub again.....
)
I'd ask the landlord if it's OK as well, if the regulars get restless then you may find yourself barred otherwise
Some tips,
- Take along a portfolio of work so they can see what type of pictures your looking to take, and always offer to supply a print free of charge.
Take a friend, ask the landlord if it's OK to take some photo's of your friend, start snapping and having your friend pose, look around and see an interesting face, ask if they'll help and then slowly move your friend out the shot. Repeat as necessary.
Imagine your income depended on you getting the shot - A great determination booster!
If you use the pub often, ask the landlord if he'd like a photo for his wall FOC (including him and his regulars), he'll surely say yes, break the ice with this shot, then ask others if they mind a couple of single shots.
Do it today, it will boost your confidence for tomorrow and the next day....
Phil