Name...

5 loved ones
Jamie, Cass, Lina, Mum and Markie!

4 friends
Cass, Lina, Talasi and, well, I don't want to pick another because that's unfair to the rest of them.

3 enemies
I don't really have enemies. Unless you count the paparazzi.

2 times you won 
Does winning Jamie count? If so then Jamie. And the other one was winning Superstar!. That was a great time.

1 time you lost
Let's pick something simple. Third grade spelling bee. Lost that to Carly Harriston who was an absolute jerk about it for the entire rest of the year.