It's mostly me who plans and asks for dates. Should I stop and see what happens?

I'm seeing a guy and it's been mostly me who plans and schedules the dates. He is always very happy to see me and was the one who asked me out the first time.

He is bit insecure but I am not sure if this is the reason.

The other day I asked if he wants to go out of town and he said:

Sure! Plan it and we will go.

Should I keep on planning dates like this?

It's mostly me who plans and asks for dates. Should I stop and see what happens?
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