Look as much as it went smoothly given the small worded reply’s you should have asked her a personal question to open her up and build investment after the soft close.

This chicks seems like a retard. But as a side note, when she asked "Why", I'd have said "So we can meet up silly". Gotta be direct in such cases when the girl is being a complete tard

For future closes ask for her number. So compliance is clear. Now you are in a weird position where you need to convince her to text you instead of you texting her.

"For romantic dating arrangements purposes" would have been a better text. But still there is a chance that she gives out the number.

like others said, you take the lead and say "great, shoot me your number" when she said yeah lets (or you could have said "great, shoot me your number for romantic date arrangement purposes."

Also agree with others about building rapport. After your bet with a guaranteed win line I would have said either, okay so give me some of the basics "any kids, tattoos, pets, felonies or crazy exes?"

Or I would have said, "how's your wild Wednesday or wild weekend or sunday funday" etc depending on what day it was. Then you could have hit her with the workout line and seeded the soft wine close there.

Another option would have been to ask her "so what are you looking for on here?"

Anyone has any suggestions on how to re-engage or continue this conversation? I'm thinking: "If you feel more comfortable, we can continue talking on here"