My friends (mostly all guys) and I are all picture whores, so I'll respond. There are a lot of excuses you can make even with random strangers on the street. I've done it. It works and a lot of people love to help a good cause:
My girlfriend is (in the hospital, deployed, with her sick grandma, bla bla bla) and can't be here with me so I'm taking her with me digitally. I'm taking pictures of myself doing all these things so she can still share the memory with me and imagine being here with me (you can paraphrase in your own words).
Take a friend or friends with you for a picture day. Go to crazy costume places, dress up like pirates, take pictures with wigs on, etc... and yes feel free to drink as you do this. Just not too much, you don't want to get kicked out of places.
Take a friend or friends with you and tell strangers you're on a scavenger hunt as part of orientation into a college group or some other legit reason, and you need your picture taken in these different poses... it's really fun if you can get total strangers in a park to do a pyramid, etc.. so it all depends on your bravery...
As far as natural solo pics of you, hold the camera at an angle and take a pic... or use your webcam... or like some of my guy friends do, when they are skyping me on their webcam, I can actually take a picture of them and send it to them... that is even better.
Just get used to taking lots of pictures and picking out your "best." What turns me off in online pics: guys who all they do in every picture is flip the camera off, stick their tongue out with nasty food on it, give all these "sexy" poses when they are not sexy to begin with, etc..
Good luck.
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Hell how do most of you get ppl to take pictures of you period?
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