(24/05/2015 03:53 AM)S7* Wrote:  Weren't sold on his thoughts?

"I don't know if I'm doing the right thing. Maybe I'm just being egotistical. But Isla... I want her to enjoy every moment as much as she can."

Well I'd consider them genuine, but either slightly unrelated to dating (i.e. wants her to enjoy life in a general sense, but in this case, wants to satisfy his interests), or worded in a fashion to make himself seem more laudable.

My reasoning is based off the typical anime male protagonist being completely clueless in regard to the girl's thoughts, and that Tsukasa seems to fit that mold.  In other words, he has no clue whether Isla would be interested in going out on a date, whether she'd do it out of interest (enjoyment?) or sympathy, or whether he could make her happy.  Of course, you'd try to make the girl happy if you take her out on a date, but the actual request itself was most likely for his own sake rather than hers.