killerman said:
Ok, sometimes I'm on a date with a girl and she tells me how she's a little awkward/shy and that she fidgets a lot. Then I'll say "yeah i'm awkward/shy/fidget a lot too" in order to connect with her and relate to her better. Basically she'll tell me things about herself which show a bit of insecurity and i'll tell her i'm the same too in order to connect better. But is that the right thing to do? Because I know you're not meant to reveal anything which paints you as not confident/powerful etc. But then again you're mean to show that you can relate to her so is it the right thing to do to tell her you're a little awkward/shy etc?
Killerman,
Relating to a woman does not involve revealing that you share the same insecurities. According to me, truly relating to a woman in a conversation is mainly on cold read and confident/relaxed facial expressions. You should check out Chase's article on being a good conversationalist to start off. The right things to say mainly depend upon the mood and the environment you guys are currently in. According to me, telling a girl you're a shy person is not a good thing. Although i do remember also reading an article on how shy is also sexy if portrayed right. But in general i feel its a no-no.
One of the things you could relate with her would be common interests (but she should do most of the talking and you should mainly be agreeing and giving a short monologue on how you like the same thing too, don't overdo your part)
Other things include:
Commenting on any quirks which are unique to her
Her Appearance/Dress (E.G. thats a nice necklace/you have an amazing sense of fashion/you have an air of mystery around you/your eyes are beautiful....which part of the world do people like that come from?)
Slowly and sporadically including flirty statements in your conversations
Gradually increasing the sexual comments (Remember they have to be subtle and increase only as you keep increasing your non verbal stimulation with her i.e. Touching her, holding hands, using the 4 different kinds of touch etc.)
Remember your main aim is to get her to your place and that requires a proper beginning and end. It should be gradual and smooth. Skipping any phase will just make you come off as a creep/pervert. There has to be class mixed with sexual innuendo in your conversations and it should be gradual and not rushed.