Would you consider this weird or creepy?

I would consider it VERY creepy. You should tell your mom and be sure to always have your doors/windows locked, even during the day, but especially at night. I think you should definitely tell your mom as soon as you can, and be sure to stay away from the dude. If he continues to try and talk to you, pretend that you really have to go back inside for some reason (like you think the phone is ringing, it's time to feed the dogs, you REALLY have to pee), something like that!