As far as it being a Win-Win, I'd consider it a Win-Win for myself as well. If it works out, it was a great weekend and we'll remember it fondly. If it doesn't work out, it was a great weekend and I have an awesome story.

Either way, I have no ragrets[0].

Edit:

I just realized that when you said

> Ok that concludes $1200 for just a Coffee!

you probably meant that I paid $1200 in exchange for the coffee (which she bought me?) so my dinner comment doesn't really make sense. However, she only bought herself a coffee - she didn't pay for any of my stuff.

Edit:

Speaking of awesome stories, have you seen the metro trains in Montreal? Those things are ridiculous, they honestly look more like subway cars attached to the bottom of a bus.[1]

[0]: http://i.imgur.com/OG2hHwW.jpg [1]: https://c1.staticflickr.com/1/28/50546136_b729b4c9ca_b.jpg