Help please!! How do i chat up a girl, so she will go out with me?

Im a 27 year old man and i have never had a proper girlfriend the only type of relationships ive had are horrible flings with girls i didnt really like but threw themselves at me! I think ive learned from them not to sleep with someone you dont want a relationship with. Ive recently lost some weight and have been going out with my mates on 'the pull'. They always seem to get these gorgeous girls and i dont know how? Im attracted to girls in their early 20's and try to talk to them but it always feels awkward like im auditioning to b their mate. Im a funny guy but i dont think it comes across coz i have an out there personality and unless you know me it seems nuts!! When im chatting 2a girl, sometimes the talking stops and it feels awkward and i dont know what to say?? When should i try and kiss her or ask her out? It might b2soon or she mite laugh and say no way!! My friends say im a good looking guy but i am losing some hair? Advice please, I want a girlfriend? Why is it so difficult?Help please!! How do i chat up a girl, so she will go out with me?
From a girl's perspective, it sounds like you are trying too hard. If you over-think chatting up a girl, you will freeze up and flounder because you will be too worried about what she is thinking instead of just being natural and acting like yourself. Talking to a stranger you are interested in is nerve-wracking in itself, but don't forget that girls are just as nervous as guys. I think girls have it easier because guys tend to be the pursuers. The key is that you don't have to worry about saying something extremely funning or charming to get a genuine person's attention. Just be kind and sincere. Pay her a compliment to break the ice (i.e. tell her you like her shoes or comment on her jewelry -- ';Where'd you get those earrings?';) We love it when a guy notices little things like that, plus you will come across as nice and not looking at other things (like our boobs, ha ha). Ask her common questions: What's her job? Is she from around here? What does she like to do for fun? This will help you figure out if she has similar interests to you or is someone worth conversing with. If you think she's interested (i.e. maintains eye contact, laughs with you, smiles a lot, flips her hair, leans toward you -- firts back), then ask if she minds if you call her sometime and get her number. As far as kissing goes, there is no secret formula. You just have to feel your way through it, because everyone is different. I have kissed guys on first dates, and I have waited to kiss guys on 5th or 6th dates. It all depends on the comfort level, the context of the situation, and the chemistry. It's just something you have to gauge. You sound like a really nice guy. I hope this helps! Best of luck to you!Help please!! How do i chat up a girl, so she will go out with me?
flirt with her.. kiss her when you know its time :P

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flirt with her.. make it obvious that you like her and you want to spend time with her.. hold hands with her too.. make her aware about your feelings for her
you cant come off like your trying hard. I love when a guy spots me from across the room and smiles a little, right there i know hes interested. After that just be yourself. Most girls love a guy who is funny, just know when to stop. (As in leave the knock-knock jokes for another time)
Kristidotson87@yahoo.com.......for anyone who wants to ask about interracial dating or dating someone older
Play cool. Girls like challenges. If its too easy, they'll soon lose interest. I suppose you may ask them out if you think they show some interests as well. Also, this may sound cheesy - but practice your kissing technique as girls will never forget any good kissers. Good luck :-)