The dating show is when your tama gets married (On other versions, the matchmaker comes). You use the dating show when your tama is old enough to mate. There is no cheat on how to get to use the dating show over 3 times a day.
Actually, there is. Change the time so it's 11:59 PM and wait 60 seconds, then change it to the correct time. Then go to dating show and you get three more chances. To get Violet Family I did it for a half-hour with no success. I finally found Sukatchi the next day after using the cheat once