Flights, hotel and Airbnb reservations, renting an SUV for 7 days, tickets for the ferry to Westfjords, etc. it was about $3500 for two people. That doesn't include food, tickets for local attractions, etc.
> Did you pay the travel ticket for her? If no, how much money she spent on you and how much money you spent on her?
Nope. We pretty much split Iceland evenly, we just went there as friends.
I fully covered Montréal because it was my idea and I didn't expect her to contribute. That ran me about $1200 for air fare and a night in the hotel for the two of us. I fully covered that along with cab rides, food, tickets for local attractions, etc. The only thing she paid for was a coffee while we were waiting to board our flight.
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