I agree that it might be best to find something so distracting that you barely notice the time. I don't see why it should be an issue to just send a text at say 10 pm to say what's up and where the night looks to be heading. It is also a matter of her telling who she is with that she will get in touch with you at 10 and would like to be home by such and such time. That way no one is left in the dark and the date can follow a natural flow of time, rather than everyone guessing where it is going to go. There is no need to get it all done in one date anyways. There is lots of time and other dates to look forward to. Why not plan on a certain number of hours and then if things aren't accomplished then make a plan soon after for another date.
When I have dates with my partners I usually set a time frame. It just works better. There are no expectations of more or less time that way and whatever we are doing is accomplished in that time frame. For instance, last Saturday I spent time with my boy in the morning, then I went for a hike with derby from 12 to 6.30. We had dinner in that time frame too. At 7 I was at Mono's house for the evening and stayed until 1 the next day. Nerdist knew that I would be home then and that he would have a chance to go out then as that became my boy time. He got home at 3.30 and we had family time for the rest on the evening, until the boy went to bed and then it was me and Nerdists time together. Everyone knew when I would get there and when I had to leave. There was no expectation or issue, it's just how it works best with more than one partner. At lease for us.
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