I'll go a bit more indepth. For the 'Love Ending' you know you're on the right track if after round 1 your first response is asking the girl why she wants money (choice 1) with the follow response being "You can't be happy with the money you get by deceiving people" (choice 2). Mid round 2 you'll want to select the options that lead to an option that says "I never contacted you" (choice 2 then 1). Do this twice then win the round! Afterwards the first dialogue choice you should see is "You should be aware that you are doing something wrong", select that. If you don't then start over and try again. For the second selection you choose the top one again (something about beauty, don't think on it too much). Talk to her again and choose the bottom choice about changing her mind, followed by "I'm serious!" which is the top choice. Do this twice if you want to (you shouldn't have to, but if you wanted to be extra safe go for it), but you should be locked in from that point because she'll be on the ground after you defeat her a third time.
As said in my original post, Hell has the route to Test end. It's the exact same choices I've explained, BUT you need to lose round three. Don't even need to talk with her, just lose so make sure you don't have defense so it'll end in two seconds.
For Daddy Life you're going to selection option 1 and then 1 again for the mid match conversation. Then fuck her. Make sure her sensitivity is maxed out so she cums when you do. Post match select option 1 about promising sex, then select option 1 again about it being legal because she felt good. During round two talk to her and select the choice about being her daddy followed by the option about giving her money (self explanatory where this is going). Fuck her again. Post round 2 select dialogue option 1 in regards to taking responsibility, then select option 1 again about the child needing a parent. (Honestly I couldn't tell you if this matters or not, but it worked for me.) Round 3 speak to her and choose option 2 about making money and follow that up with option 2 again about being exclusive. Fuck her one last time. You've unlocked it if she's on the the floor and your character is tell her that she won't get knocked up. Again if it doesn't seem to be working, then do the mid match conversations for rounds 2 and 3 at least twice before proceeding.
What may help to get Daddy Life and allowing the girl to orgasm mid fight of each round. Quickest way to do that by knocking her onto the bed, binding her, let her cum, then proceed to have sex immediately after (though I tend to build her meter up a second time to ALMOST climax then do her because she reaches maxed state almost instantaneously that way when you go to have intercourse). Also I am uncertain how much of a role the prologue dialogue actually has in the choices so for all I know those can be skipped and these'll still work. Don't take my word for it though.
Good luck.
