I feel like the interaction ended on a high note so I didn't want to press for another date tonight. You think I should hit her up with a "how are you feeling" tomorrow and maybe throw in something about helping her de-stress with a massage?

She’s working both Sat/Sun so I’m not sure when I should try to schedule a date. I’m kinda free Friday but don’t want to jump at every night

I used a variation of Alex's "if you're nervous about meeting up" line and she opened up a bit about a rough few days she was having. I gave a comforting response and we joked a bit. She ended with "gimme another chance?" In retrospect I should've given a flirtier answer, but I just said "I'm down" and ended the interaction. It's gonna be a work in progress but I was able to stay cool and collected throughout so hopefully I'll be able to make something happen.