I have a bad feeling about this.....Suggest Advice
Do you have some advice for this person?
Okay so I met this girl on an online dating site. She lives close. We have alot in common. We like to talk. We're really close in age to. However in the past I would either ask the girl out too late or too soon. And the ones I asked out at the right time turned into horrible relationships and I lost friendships with each person I asked out. This is hard since I help people with this but for some reason I can't do it right. So how would I go about asking this girl out in way that won't make me seem creepy or make me lose this friendship let alone get stuck in the like a brother or best friend zone?
Aha, so you know about "the zone." You can get stuck there when you wait too long to ask someone out and they only see you as a friend/brother at that point.
How long is the window of opportunity open? I'd say if you don't make your interest known to a potential girlfriend within a month, you've probably entered the zone. The window can be open longer or shorter, of course, depending on how much time you spend together. Only you can really make that call. Time spent dating will give you that experience.
But how soon is too soon? It's nice that you want to establish a friendship first. Don't stop being that kind of thoughtful guy. But you can still be a friend AND show romantic interest. I think showing wooing behavior from around a week or two after meeting is perfectly appropriate.
Look around on this site for help and information on courting and wooing a girl. Study the techniques and have courage. You seem like a nice fellow, so you should do fine.
--Your Friendly Advisors at RomanceClass.com