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'Daddy Issues' can happen once Day 3 starts or during the day on Day 2. I don't know if it has a friend requirement or not but I had over 60 friends on day 2 and I was able to friend him.
As for Daddy Issues, it may be due to Clyde. I am not sure. As you know, Clyde defriends you early on. You have to befriend him before the tutorial. This may play into the Daddy Issues achievement, but just hearsay.