Do you feel like you and your SO have the same fight over and over again?

My DH and I always have the same argument on how his excitement/effort/planning level(s) is not the same as when he goes out with his friends as they are when he goes out with me. i.e. His calendar has been planned out for the rest of the year with golf outings, a trip to Vegas, and a handful of football games. I encourage him to spend time with his friends, it is healthy. Yet he scoffed at me in getting a reservation for dinner for our respective birthdays saying it is 2 months away (it really is 5 weeks). I also mentioned we should get another date night on the calendar and he said we just had one (that was Aug 3). *rant*

Am I being silly by always bringing this subject up? Obviously we are having this re-occurring issue, because it hasn't been resolved. I've voiced my opinion and my feelings on several occasions and still no resolve. Do any of you bees have advice or similar issues?