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Welcome to the forum, Hank. Hopefully we can help you iron out your issues.
Thanks for the welcome
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Are you trying in person and online as well? Where are you doing your approaching? Is it day or night?
More online than in person, as, like I mentioned, I don't know how to approach those outside my social circle(which is pretty small to begin with), and I have to be careful who I approach within my social circle because I fear that if I mess it up with one, the rest will find out and avoid me.
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Your fear of coming off as a creep is all in your head. Women are generally flattered when you speak to them or smile at them... Even if they reject you. Everyone likes being hit on.
A LOT of girls go for slightly older guys too (my girlfriend is 26. I'm 36). Don't be afraid to risk being seen as creepy, man... You'll never see these people again anyway - so put yourself out there.
While it's true from my limited experience that some girls do like older guys, most will see an advance from a guy more than 10 years older than them as being creepy. And because I live in a rather small town, once a guy is labelled as a creep, words gets around. So I really need to be cautious.
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You may not be escalating while you're talking. You need to identify yourself as a sexual option and make your intentions clear (without actually making your intentions clear... I know it's confusing). Don't say you like her. Show her you like her. Touch the small of her back, or her arm, or her leg (not in a creepy way) and use kino wherever you can... Smile. Eye fuck. At the end of the conversation, instead of saying goodbye, you say "Hey you seem like a pretty cool girl. Let me get your number" and hold out your phone.
Yeah I suck at making physical contact, especially since I'm in an Asian country and physical contact between the opposite sex is not common, even amongst friends. I really need to learn how to do this in a way which won't raise red flags for her all over the place.