1

Tokyo is the far better choice for dining and nightlife. And there's plenty of sightseeing too, much more varied than what you'll find in Kyoto. If you want to see what Japan is really like, pick Tokyo; if you want a quaint tourist experience, then check out Kyoto.

2

Even though he may be "willing" to go to Tokyo to meet up with you it will either be expensive or time consuming to do so, especially for such a short time. Even more true if he is working on Friday and can't leave Kyoto until after he finishes work. I wouldn't even call that time two days depending on the exact times you are talking about.

I'd strongly suggest just going to Kyoto. Considering you are only there for two dinners there are plenty of decent options in Kyoto and if you can't find anything reasonable then Osaka is only a short step away anyway.

For getting from Kansai Airport to Kyoto and back I'd buy the ICOCA + Haruka package:-
http://www.japan-guide.com/e/e2359_icoca_haruka.html

I'd possibly do Friday night in Kyoto, Saturday in Kyoto and then Saturday evening in Osaka perhaps.

3

(It takes two hours and twelve minutes to get from Kyoto to Tokyo. If I lived in Kyoto I'd be thrilled to get away for the weekend)

4

If you want to see what Japan is really like, pick Tokyo; if you want a quaint tourist experience, then check out Kyoto
I disagree. Tokyo is a great metropolis and beats Kyoto hands down when it comes to neon lights and modern architecture, but Kyoto is the place to head to if you want to get a feel for traditional Japanese culture. Osaka is just half an hour away by train, so you can always spend a day experiencing a big Japanese city. Overall I would always chose the combination Kyoto/Osaka over Tokyo.

It takes two hours and twelve minutes to get from Kyoto to Tokyo. If I lived in Kyoto I'd be thrilled to get away for the weekend
To each their own. I lived one year in Kyoto and, apart from the occasional Saturday night out in Osaka I enjoyed my weekends there a lot. OTOH, when I lived in Tokyo, I was glad to be able to escape the ugly urban sprawl and its endless crowds after two weeks.

5

And costs 26,000 yen (assuming he has a work visa, or at least no JR Pass). You could eat and drink a lot in Kyoto or Osaka for that sort of money!

6

Yes, and OP could skip the flight to Japan and really eat well! Presumably if the friend is willing to go to Tokyo, he doesn't mind going to Tokyo.

7

Thank you for your opinions! We haven't decided yet but I'm sure we'll have a good weekend! Cheers!