Today's question comes from Anonymous, whom I've affectionately dubbed Phil.
He writes: "How do you recommend approaching women like you who run or go to the gym? (By the way, I am a charter pilot, we pilots have a hard time meeting women)."
My answer: With caution.
It's hard to approach a woman at the gym. We're usually focused on the task at hand and in quite precarious poses (on the pilates ball, doing a dead lift, etc). And we naturally assume that guys are ogling our tits and asses. Therefore, guys who do approach us at the gym seem kind of creepy (though I'm sure you are the exception to the rule Phil ;) Besides, we want to get in and out without guys noticing that we're not wearing makeup, have a wedgie (or worse...camel toe) and a bad case of boob sweat.
It's much easier to approach a woman runner (from behind) and say something complimentary like "You've got a great pace". But only if she doesn't have an MP3 player or else she might mistakenly assume you're a mugger and go Taebo on your ass. And naturally, we'll still assume that you were ogling our asses.
It's a dating jungle gym out there. There's no "right way" anymore when it comes to dating and mating. There is however the "gentlemanly way", the "jerkoff way" and the "have been in prison too long" way. I find being irresistibly charming and direct always works.
Hope this helps Phil!