Should I kiss him on New Years?

I really really like one of my best friends, he knows that, and when we talked about it a few months ago he said that he doesnt want a girlfriend right now, but that he would date me someday, and that he would be willing to be friends with benefits with me (not someting that happened, was just a random question that came up, but i do know for sure that he liked me), but ever since we talked about it, we haven't been talking at all, and hardly seeing eachother. In the past we have held hands, and cuddled a few times, but i really just want to kiss him. However, i am terrified to do so, and need help finding the courage. Were going with a few of our close friends to the spaceneedle in Seattle on New Years, so i'd kiss him at midnight. But hes not into PDA, so im scared that he'd reject me mostly because of that. I know that even if he didnt reject me, it'd probably still be awkward after that, but its not things are going good with us anyways. Any advice on how to go about it, or encouraging words??

Also, i have a photoshoot with him two weeks later, which involves us being somewhat close and sensual, so if it went THAT badly, i'd have to consider finding another guy to do it