Those things you've asked are all standard 'small talk' repertoire for me. Perhaps you're not working well enough with your second and third comments?
After you find out where she works or where she's from, try some open ended questions. "Oh, so you're a country girl. How was it growing up in the country?" and let her run with it. "oh, you know John from College....what was he like back then?". "You're in advertising? How is the current economic downturn effecting your business?"
And if there's something you can relate to, feel free to add in some comments.
Never regret anything that has happened in your life. It cannot be changed, forgotten or undone. So, take it as a lesson learned and move on.