Heart Breaker?

Ok. So VERY recently, this guy asked out one of my friends (over text message by the way.) And since, they have been going out. He does all these sweet things but you would NEVER have expected it from him! Not only that, but this was really unexpected. (REALLY UNEXPECTED!) No one would have ever thought that these two would go out with each other! I mean, sure, they're friends and my friend did have a crush on him but never did any of us think that she'd actually become his girlfriend!! He wants to hang with her this weekend for their first date and I'm really happy for her but I can't help but have a twinge of doubt in the back of my mind. Is he just toying with her? I'd say they last at least a month but I'm not saying that her heart's not gonna get broken...
I hope that none of you guys have but, have any of you ever toyed with someone's feelings on purpose? Did you regret doing that now? (Ironic that my username is NoxxRegrets, right?)