How do you know if a first date went well and if you should pursue another? some background:

>Go on date with girl that used to have a crush on me in high school
>coffee date(she paid), maybe lasts an hour and we're talking almost the whole time, lots of eye contact throughout

>about an hour in she mentions she should probably be getting back to work(she works from home)

>I decide to let her like a dummy cause I think its polite
>we go to my car, she asks what I'm doing tomorrow and I half assedly say I'm not sure yet.
>we struggle awkwardly to say goodbye to one another. eventually she leaves and looks back at me as I pull out of the driveway.
>Feel like I fucked up...again.

Anons, from this brief description did I fuck up? Should I text her tomorrow and pursue a second date/try to kiss her or something? She's not staying in town long and this was kind of an out of the blue catch up. I'm not even really sure it was a date.