I do schedules my dates with my boyfriend like I'm scheduling a business meeting, but somehow, I'm okay with it. And on the upside, scheduling it our time together a week in advance or more gives me something to look forward to when my week is less then splendid. I choose to look at the time I can spend with him as a gift, rather than feel bad for the time that we aren't together.
In terms of keeping everything straight, I've pretty much ditched the date book for a google calendar. My roommate, my husband and I all have color coded calendars that we share so any one of us can see what's going on with everyone.