Let's see I guess I have now about 40 some years of experience with women. Waited until 30 to marry. Guess I have dated maybe 60 or more girls/women in my checkered past.

My experience is that it almost always ends up with either the man or the woman being the more dominant person. The fact that you feel the need to ask advice about where to take a woman, who is 3 years older than you, on your first date says a lot. You can't really change your existing level of confidence, but you can try to pretend.

If you are that insecure about something like this, then I will bet that she will be less than enchanted with you. Don't know whether you can pull this off, but trust me. Most women are attracted to a man who is not in pursuit mode.
The more you act like you have other choices, the more interested she will become. Pay attention to whether the conversation is effortless or whether it is strained.

So just decide already and ask her out.

Steve