I Have a Question

I recently just bumped into a Friend of mine that now works at US Bank in Downtown, Minneapolis. In the process, I met her work Acquaintance. They were on there way to Caribou Coffee. Anyways, I could've swore to myself that I saw her this morning on the way to Caribou this morning but furthermore, If and when I see her again, I want to know if I should ask her out for Coffee sometime? She is very pretty. What should I do?