Ten Dates

If you don't earn this from your first playthrough, subsequent playthroughs allow you to choose which people you want to try and date, so you can make this nice and easy by selecting just one person.

Here's how I got it.

Select Azalea and choose the following dialogue options:

> Looks gross.
> Why speed dating?
> Move on.
> What's your type?
> Different to you.
> Nothing.