Something odd.
I'm using the new version and started a new game. I'm a week or so in (first leaderboard reset is going to occur in 5 days). Rogue came and suggested being more than friends a couple of days ago. I enthusiastically agreed.
I can't set up a date. I checked the in-game database just in case I'd forgotten how the UI works, but it says it can be set up via text. There is simply no text option for it. I've checked at different times of day, but there just isn't an option to ask.
Any ideas or suggestions?
*edit*
Nevermind. She just asked me again. Maybe I screwed my reply the first time.