As the former host of Punk'd, Ashton Kutcher is definitely used to both inspiring awkwardness in others and being awkward himself, which obviously also bled into other aspects of his highly publicized life. But back in 1998, the actor was in the middle of starring in his very first TV show and had none of the Hollywood know-how that he would go on to pick up in later years. So at that point, he's basically just an excited and scrappy 19-year-old dude being told that he has to start kissing his 14-year-old friend and co-worker. It's hard to imagine how that job task would come up on the set and not be awkward in some way.