Moonfroggy, do you have a friend who could come with you to the bike shop? I'm thinking having someone you're comfortable talking to could make the exchange easier, someone to fill in the gaps, make small talk, ask the little questions you may not think of etc., take the pressure off of you having to handle all the dialogue.
Any bike shop employees that know anything at all about biking will know all about saddle pain and the importance of a good fit, though, so expect them to take this in their stride. It's essential to both men and women, beginners and veterans alike.
Re your problem directly - I've never bled, but I have had bad chafing that I didn't notice until after the ride, because of compression I assume. Moving my handlebars closer to me with a shorter stem helped, a saddle with a larger cut-out and the right tilt helped, and changing my riding position around a lot on long rides helps a lot. Standing, sitting, sprinting, change is good.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett