Thank you
@Metropolis Man The most challenging part here was to get as many phone numbers as possible on the first day.
My strategy was to create a club with only single sims in it (we can choose that while creating a new club) so that it would be easier to flirt with them.
Since day 1 08:00 am,the club was always into meeting (chosen activities were socializing and flirting). For each targeted sim I chose "compliment appearance" and then "exchange phone numbers". I was only rejected one time but was successful 41 times.
As soon as my sim had another sim's phone number, I removed this sim from the club and replaced him/her with another single, in order not to lose too much time.
After the first day the dates began, and it was easy to get gold medals for each one.
The club was always running during the dates (but always with sims that had no romantic interest with my challenger, to avoid jealousy!) and with the "rally the troops" interaction my sim was able to be always on a date and had enough time to date her 41 "phones numbers".
My sim always got the gold medal (and the first kiss) at approximately half of the date. It was easy thanks to the club meeting always running: I chose the romantic atmosphere perk (at level max) ans always put the dating sim in the club during the date.
My sim finished the 41 dates on Saturday 22:30 pm, so she could have get 2 or 3 more dates but hadn't any more phone numbers!