How about some burnt, bitter coffee at Starbucks with a thawed stale danish? That would be a great start. However, good coffee and talk wouldn't be bad.
A real date with a new person would depend on conversations beforehand. It should be unplanned, but with some things in mind. Part of beginning to know someone is hearing their voice describing themselves and their sense of life. What's funny and interesting which grabs their attention. Their cautions and what they would like to do all gives you some insite into what your date should be like. Maybe some music, a restaurant and a walk to a pier or seaside garden, so that you can have fun understanding more about each other. Now would be the perfect time for a tastless Latte and hard plastic chairs at Starbucks for the end of an succesful, intimate date.
Later when both of us have time to sift through the nervous stuff and get to the point which might tell whether the first date was nice or perhaps fun enough for a second. If we're both still interested, the next date can be more mutually comfortable and the second date can be a lot more fun. If she's not afraid of sailing, a day on the water, stopping for a fresh seafood lunch at a creek pier, and then watching the light change as you come back in. Other wise a night eating Chinese or Cuban food, then a live band at the Pour House, followed by drinks on the rooftop bar on East Bay Street. Where are you interesting ladies...