Rules are great, but I'm learning to be flexible with them. We used to have a rule that she would text when the date showed up, and then 3 hours after, and then again, if she decided to spend the night, or if she needed a ride home. (She doesn't have a car)
This wasn't easy, at first. I'd simply be wringing my hands the entire time, wondering when I was going to get my checkpoint texts. When things went especially well, I'd go for hours after the mid-point text wondering, "Does she need a ride? Oh crap. I'm not getting any texts, so they must be having the best time two people have ever had. She's going to replace me."
Normally I'd get a text at about 2 or 3 in the morning (she's a night owl) telling me she was staying over, or needed a ride home. But the first time she spent the night without texting me and slunk in the front door, we had a serious "Come to Jesus" meeting. During this period, I didn't have much going on personally, and was new to polysexuality, and polyamory, so the idea of the insanely great sex she must surely be having was on my mind, too.
When she'd come home, I'd need a lot of reconnection that sometimes felt really forced at first. We had conversations about me being needy. But that led to conversations about what I needed to feel loved. And over time... over time, her affirmations became natural and quite loving. It's still a work in progress.
Nowadays, I usually get two or three texts throughout the date, but they aren't required. There's trust that goes back and forth. She hasn't been on an overnight date anytime recently (although it could happen at any time), but I'm sure she would definitely let me know if she needed a ride or was spending the night.
Oddly, some of the best reaffirmations don't come on either side of a date. They come when we've spent days alone together and she just tells me that there will never be anyone who can replace me, though there may be other people she loves along with me. Just saying it for no reason other than to let me know I'm loved and not going anywhere. We have what in the BDSM world is a DaddyDom/little girl dynamic, so our conversations are mostly about how I'm her Papa and there could never be another Papa. How safe and loved she feels with me as my little Puddin' Pop.
If you ask the questions that make you feel secure about your relationship enough, I'd think you'll begin to hear what you need, even when it's not date night, which will make you feel even stronger on date night.