I wanna make it sound casual and not intimidating at all, this would me my second time asking her so is kinda hard :|, I'm not sure if she likes me, she's very friendly and smiles a lot but considering she's shy.
Me: Hey you free Friday night? :)
She: mm yea why?
Me: I wanna take you out, what do you say? ;)
Most Helpful Guy
Relate to how she's thinking:
If she's shy - there's GOTTA be a reason why. Maybe because she sees you as a friend and knows you're interested? Maybe she's approached by guys 24/7 who are horny and just want a quick lay.. etc
If you find that reason or can figure it out somehow, without letting her know, then you have a STRONG edge on the situation! She will see that you are trying your best, even if your intentions come across as dirt, she will see that you really do care.
A natural approach isn't walking up and saying: "Do you want to date me" because how would you feel if a gay dude came and said that do you? You'd feel creeped out and probably a bit defensive, almost as if you'd kill the guy if he didn't immediately stop what he did.
Instead, you have to SLOWLY but surely turn up the temperature.. Start by spending time with her and knowing her interests and what makes her really happy versus really angry.. When you have a lot of basic information about her (really simply to gather), you know how to treat her with the utmost respect and now how to make her really happy - just follow the blueprint you've made.
If I knew a girl was shy and loved humor, but that she was really scared about finding true love because she just got dumped after a 2 year relationship - then I would understand that I'd have to very slowly progress in showing I'm interested.. not instantaneously taking her on dates or asking her out.. but just spending time with her at school, see if she is comfortable going to the park and walking around while talking.. Show her that she doesn't need to feel insecure with you around - but at the same time don't be bashful of embarassing her in a silly way.. Like when you guys are at a dance, grab her belt loops and make her move really weird and then say: "You're so cute" and give her a huge hug.. She'll have no control over it and realize you were just playing (hopefully) but realize that you should VERY rarely use the embarassing thing, if ever. It's a spice to keep you away from the friend zone.
If I knew all of that, maybe after 2 or 3 weeks I'd start progressing onto movie dates or putting my arm around her.. Maybe holding hands.. It's all in what I felt she wouldn't be "against" but exactly what would be showing interest.. Basically, be respectful yet push her towards a relationship just a little at a time.
If someone nudges you, you wouldn't notice.. Like a guy walking past you in a crowded public area.. But if someone pushed you hard, like a guy trying to fight you, then you'd instantly get defensive or you'd cowar away.. That's exactly the concept.. You want to nudge, not push.