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I have this same problem. It's almost identical! A girl HB9, with a dogl, seen only once in a while.
I always only say hi with a normal tone, but once her dog barked at me, when I was trying to pet it (it's a really small fucker).
So next time I think I'll say something like:"Hey, walking your dog again? Tell you what, I have some time to kill, so I'll walk with you, so that the next time your dog sees me, it won't get afraid"
You guys think it'll work?
That's like saying you got nothing better to do and this kinda looks like you're hitting on the dog man. You could go with a more playfull way and say something like 'you brought your bodyguard again? Last time he tried to stop me from talking to you also, that won't stop me this time!'
Just walk with her while you talk. You don't have to give a reason before you walk with her. And use the dog for opening up so don't continue about him because it'll make her think you're more interrested in the dog than you are in her.
Of course this is just my point of view, but that line sounded rather boring and I doubt it'll get an eciting reason from her.