How do I take Pictures with friends?

Hi folks, so first off I have to say I love taking pictures with people but the thing is my friends hate the idea. Whenever we are out and about I always ask them to pose for snaps and they either make a fuss about it in public or if they do agree they always look stiff and awkward in the pictures. I recently met this guy who I am crushing on and I really want to take pics with him when we hangout but he tells me he absolutely hates taking pics something which baffles me because the dude is very attractive. Some of the few pics I do have with him aren't that great because his facial expressions in them do reveal that he is very uncomfortable being in front of the camera. I have seen pics of other people on facebook and how they eagerly pose for pics with their friends and they look like they are having a really fun time . Is there any way of convincing my friends to just loosen up and smile for the camera? Also how does one go about taking pics if there are only two people around ie , i plan to hang out with that guy some time soon and I really want to take pics to remind me of my time with him . I mean I could always ask someone random to take the picture of us but then doing so would totally make him feel nervous and uncomfortable . I would really appreciate your feedback :)