The first day was the crucial part of this challenge for me, the number of phone numbers i could get determined how many points was possible to do.
After alot of testing i found out it was best to have my sim be flirty when introducing yourself to other sims. So i set up her home to have a shower and a mirror. So i ensure i had the flirty mood when leaving the homelot. This gave me a 4 hour window to gather numbers, before returning home to refresh the buffs.
The next keyfactor was to ensure that I only talked with one sim at a time. This drastically brought down the times the sims rejected my sim. So every sim she met she would use flirty introduction, and then exchange phone numbers. As soon as that interaction was done, she would stop the talk with that sim and move onto the next.
I found out that the easiest place to get near alot of different sims where the gym in oasis springs, the retail stores, and then the nightclubs at night time, specially one in Windenburg where people would dance (cant remember the name sorry).
In the end i managed 39 phonenumbers that way.
The dates where straight forward. The home lot was setup with the romantic aura, and party place lot traits. And all dates where done long before their timer ended.
Romancing the sims on the dates also easily let them have a first kiss with my sim.