This goal appears sometime after unlocking Cannes.
You run into your rival in Cannes and they brag about how hot their date is. They start to pick at your love life and they want to see who can go on more dates in 3 days.
Depending on what you choose, will be how many dates you have to go on in 3 days. You can either choose One, Two, Four, or Seven!
For this goal you would have to choose Seven! You can date the same person for the required dates.