The Dating Game

The “Jeff” Dilemma

We all have a list of what if? people. For example, what if I told you I liked you? What if you hadn’t dated my best friend? What if we weren’t cousins?

I have one such list (although mine does not involve incest), mostly comprised of people I went to highschool with.

One member of the list is named Jeff. Jeff is blond and dresses like he walked out of a nautical clothing magazine. He is quirky and kind, and in many ways just a bit strange. He collects special edition prints of famous literary texts and is wildly devoted to the things he finds interesting. When I’m with him I get into heated debates with myself about whether or not he’s attractive.

When we watch movies he sits very close to me—I don’t know if this is intentional

or if he just has spatial issues. One day, last summer, he asked me at noon if I wanted to drive up to his house in Door County, Wisconsin, the midwest equivalent of Nantucket. The combination of my raging hormone levels, confusion about our (potentially romantic?) relationship, and New Year’s resolution to be more spontaneous pushed me to say yes. So I said yes.

We set off for our five-hour drive relaxed and happy. It was nice—we listened to chill music and just talked like we normally do. He had broken up with his girlfriend of a year and a half, Paige, roughly two months prior and was still upset, so we spent a lot of time discussing his feelings for her. Door County held a lot of significance in their relationship—they had met and spent the entire summer there together. Jeff hadn’t been back since the breakup.

We made a pit stop for snacks somewhere along the way, where he sent me the clear signal that nothing was going to happen: a purchase of Sour Cream and Onion Pringles. Bummer. I thought. At least I know now.

When we arrived it was dark outside. We put our stuff in separate rooms and sat down to have a beer, one and a half for me and six for him, a habit he picked up at his college in Boston. We were falling asleep and then suddenly kissing: more out of boredom than anything else. He kept trying to do weird stuff with his tongue, and I was not having it.

Both aware of the fact that there is no going back once you see someone naked, we silently agreed that we shouldn’t risk our friendship and stopped. I declared I was going to bed. Five minutes later he came into my room, looking like a child who had just had a nightmare, and asked if he could sleep with me. I agreed, figuring it would be nice to share a bed with someone.

I’ve since learned that I’m not a very big fan of spooning. This makes sense, considering I wince almost every time somebody touches me. Apparently, as a child, I had to be taught how to give/accept hugs. Even now, whenever I meet a European and have to kiss them on the cheek, I sweat profusely until the moment is over. I have problems with physical interaction.

It was fine—at first. Then I was overheating and ready to go to sleep. Figuring Jeff was asleep I tried to roll away from him—proud of my suave maneuvering and ability to handle the situation with grace. My comfort lasted for a whole 10 seconds until he pulled me back into place and wrapped his leg around my torso. He was like a furnace with rocks for arms, but I didn’t want to hurt his feelings by kicking him out of my bed. Immobile and conflicted, I just lay there, stiff. I slept four hours that night—for all the wrong reasons.

When we woke up in the morning we didn’t discuss what had happened. We wasted an uncomfortable 12 hours walking around Door County, both of us feeling strange about the night before, and Jeff a bit cold toward me. He spent the day trying to reclaim the places he loved as places without Paige. I spent the day trying not to fracture our friendship. It was a long drive home.