I did a photo shoot last Spring with a Comedian, Donna Lee McBride, and it took a little coaxing just to gain access to the site. Here's the resulting video and a few stills. Later on I give some tips for gaining access to a location.

Tips for Securing a location

• Be Confident and Professional
• Know what you want before you ask
• Hand them a business card
• Tell them how long it will take
• Make sure they know how much equipment you have
• Be on time and leave on time
• Tell them where and how they'll get "credit" if at all

I've found that if you do these things at a restaurant or a club they have no problem with you coming in and shooting photos of someone. I think the number one thing is confidence. You will likely have to work your photo session around their schedule as well. Don't ask if you can come in at dinner time or whenever they have their big rush. That's a bad idea for everyone. Getting set up in your favorite club or restaurant is a great feeling. It legitimizes you as a true photographer and personally I feed off of the crowd. It's like putting on a show, so perform a bit. It's okay to go for it.