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True actually. I usually go try and put my sentences as simple as possible, so I don't look like I'm trying too hard.
But there can always be expections, especially if she's a HB10 as you say

lol, I guess it really just depends on what your education level is... If she's in or graduated college, then I'd HIGHLY recommend you make sure you're using proper grammar... That being said, DON'T use big words unless she's like an English major... In that case, you might be able to DHV by making her look up an uncommonly used word... Just make sure the word is being used in the proper context.
I've had several conversations with girls I met online about how they screen guys out online... Grammar is one of the primary screening methods they use. That being said, I usually am only interested in girls who have a college education... Unless they're proven they can easily support themselves by doing something like modeling... The last thing I need is stupid little girl who can't pay for her own shit.