Another very awkward dating experience I had was having the pressure of being the first girlfriend, first relationship, first kiss, first everything to an adult of 26 years old.

Let's call my friend James. He was 26, sweet, smart, caring, and funny, but he was also incredibly socially awkward. He had asked me out a few times, but I wasn't sure whether they were dates or not because he spent most of them ignoring me nervously and talking to his friends. Once he even disappeared for 15 minutes straight after a movie and I began nervously looking for another ride home.

One night he invited me out for drinks with friends. He spent the entire time watching his friends get drunk, sipping water. Occassionally he would ask me if anything was new, to which I would always awkwardly reply, "Well.... not much in the last 10 minutes...."

James ended the evening by arguing with me over politics. I had to drive him home---of course he had no car---and I drove him home in icy silence. Once he got there, he stalled for over an hour and a half while he tried to figure out how to make a move. I waited patiently. He finally told me his mother was a palm reader and asked to see my hands. I had to give him points for creativity as he moved cautiously from "palm reading" to hand-holding.

Finally, James admitted to me he had never had a relationship. He'd never even gone out on a date. Apparently he was just too shy. I, however, was reticent to start a relationship with someone so inexperienced, since I flew out the Puberty Gate at 12 and have been steadily dating one, two, or three boys since then. But he seemed cute, in an odd way.

James didn't know to let go of my hand once our palms got sweaty and clammy, so we waited and made quiet chit-chat while my car turned into a sauna and the windows began to fog over. Finally, he hugged me, then asked me, "May I kiss your lips?" It was his first kiss, so I didn't judge. He was actually quite a lot better than most people I kiss, proving that experience isn't everything...it isn't even much.

In the end, James and I didn't work out because, as I feared, he wasn't ready for a relationship. Someone just getting his feet wet with his first girlfriend is more at home in a high school setting than with a confident, experienced adult woman, and he realized that and backed out soon. I don't blame him. But I still always remember the night that, to my utter incredulity, I taught a 26-year-old to kiss.