Welcome! You might try Stephen Ave Mall. Usually lots of people there, with the more interesting people appearing later on in the evening. Following the LRT downtown is also interesting. This time of year, the Stampede brings out lots of people but with this weather, I do not know. Cheers!
kensington and inglewood are kind of trendy. In between you have a large downtown. Then you have 17th Ave from macleod trail west and Stephen Ave.
If you want something more scenic, the peace bridge and princes island park. You could make a whole day out of everything I've mentioned. If you want something lower income, 17th SE aka international avenue but I wouldn't recommend it.
Try Rope Square on Saturday - Downtown at Olympic Plaza. Here is a link that will give you an idea what happening there. http://stampede-downtownattractions.com/