She did let the guy at the restaurant feel up her boobs... then told the MC. she did not know he was watching. could be the same here... she saw how he got off in bed when she told him.
In the fast date, something happened that the MC and Nicole planned for, had talked about before, and both were ready for and had both agreed to
But what you're saying could be right, the problem is we don't know where the MC's cuckolding boundaries are. Has he told Nicole that wherever she goes, she can have fun with other men? The cuckolding path is ambiguous, there's a lot we don't know, maybe we'll find out in the next update