After 5 dates, his texts + urge to see me hasn’t changed much. He doesn’t plan too far in advance + I wonder how he feels. Am I expecting too much?

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It sounds to me like you guys are looking for different things. What do you mean exactly by “moving the relationship along?” To be honest if I heard this as a guy it would make me immediately pull away. A relationship is not a truck, it’s a garden. You plant stuff in it and water it and hope whatever