Establish early on if it’s a proper date, or two friends/ work colleagues having a drink. Then all good, act accordingly. You must know in your own mind if you asked her out because you fancied her or because you wanted to be a nice friend. Tbh, whilst I accept I make most drink spillages look deep, if you are just meeting up to offer a shoulder and talk about the deceased and how she has adapted, kill me now!! But being blunt, someone’s going to get there first if you don’t, and if you fancy her fortune favours the brave in my book. But if you just want to be a mate, steady on the booze and knock one off before you go. Just don’t be a prick.