So after reading this I decided to call Singapore Airlines and check to see if the segments were confirmed on their end. They confirmed that they were waitlisted.

I called Aeroplan and let them know. They had a supervisor pull up the ticket and they could also see that the ticket was in waitlisted status. They tried rebooking it 4 times and it kept on rejecting it for the SIN-DPS. After waiting on hold for about an hour they came back and let me know that they had booked me a paid J ticket on a separate reservation. Just checked the original reservation and I was able to select seats/book the cook

Thanks for everyones help!