Spoiler below obviously 
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To go on the date with Paige you need to talk to her downtown. When you first interact with her say “No, but you’re going to want to know me.” “And it sounds like you have some daddy issues”. " I can help you get back at them." " No, I’m not doing that." Then you need to “Double down.” Then click the leave button from the downtown screen. This will trigger the Paige date event that can happen in the evening.