Lots of good advice in this thread, here is my single female perspective.
It hasn't been a problem for me but then again i've only been on casual dates with non-dubs. Religion doesn't come up mostly and when it does i explain that i was bought up in a very religious household. If appropiate, i may share some aspect of my JW background but it's definately not THE topic of discussion on a date.
As for holidays...i go with the flow. Holidays don't bother me so i don't stress out about them. Decide what your current position is on holidays, your level of comfort. Are you comfortable celebrating some holidays and not others? Focusing on the non-religous aspects of the holiday helps (using non-holiday related cards, wrapping paper etc). Give if it feels right, don't feel pressured or obligated.
I'm a paralegal without a degree or certification; how i got in this field is a story for another day. But I always felt inadequate of my lack of education. No one ever judged me (at least to my face), it was my own thoughts and feelings about it. So i've gone back to school for my own peace of mind. I think that if you are a happy, adjusted and self-sufficient person, most people wouldn't not care about your level of education.