My Search for Prince Charming’s Normal Brother

Chapter 1: Cranberry Wrong

Holy hell! How did I manage to get myself into this? (Enter harmonica music at 1:00 a.m.) While I trust that my co-tenant neighbors appreciate the harmonica serenade, I am getting creeped out. Thank God he doesn’t actually know which unit I am in! Time to call the Boston PD.

So it all began, on a dreary, damp morning in Boston. I was running late, with my briefcase and umbrella in tow. I was fairly certain I could have doubled as a wet terrier and that my face showed my displeasure as I waited for the train to approach. I actively looked past others at the T-stop. Not exactly an elevator level of civil inattention, this is a new brand of ignoring others—I think it’s a Boston thing.

I had just missed the train and knew it would likely be another fifteen to twenty minutes until the next train arrived. So I was deep in thought about the day ahead and the multitude of e-mails I would already have. “Thanks for missing the train,” I heard. Dah-dah-dah. Again, the male voice said, “Thanks for missing the train.” Oh, he’s talking to me—he must be from out of town! I looked over, and to my left stood a tall, dark, and handsome type with a wide smile.

I looked at him and responded, “Yes, I just missed it.” Thank goodness it was raining, because I would hate to start this day on the right note.

He was still smiling at me at this point. Realizing I’d exhausted my store of witty pre-9:00 a.m. remarks, I didn’t say more. Then he responded, “Well, actually I am glad you missed the train. I have noticed you around, and I have always wanted to introduce myself. See, I live in the area, and you seem so nice—are you new around here?”

“Yes, actually I live just down the street,” I responded. By this point, the train had arrived and he boarded with me and continued the meet and greet.

He said, “Welcome to the neighborhood. I imagine someone as pretty as you probably already has a boyfriend.”

I said, “Well, not exactly.” I smiled and tried to think of something to respond with. He then asked if we could grab coffee or a drink sometime. Sounded like a fine idea, since I wanted to meet new people in the area. At this point, I decided that if he wasn’t for me, I could introduce him to a couple of other single women I had met in the neighborhood—it would be good for the community. A kind of recycling. Brookline likes recycling, so why shouldn’t I?

We exchanged numbers and chatted more. I was feeling flattered that someone had taken the time and effort to approach. He seemed nice, and besides, how bad could he be?

A few days later, knowing that I worked downtown, he called to see if I wanted to meet him for a coffee. He was a freelance writer-musician and a self-professed dream catcher trying to trying to work out a plan for his life. He was rushing into this decision, since he was only in his early thirties. From our discussion, I could tell he was pondering many different career options. One option that came up related to his experience as a preschool teacher. This apparently had fallen through and involved some kind of issue for him. After I noticed he seemed to be getting teary, I decided to move the discussion away from this topic. He mentioned a couple of other career options, even including the possibility of being an orchestra conductor. He had an ear for music, a talent with instruments, and what the hell—his friends said it didn’t look that hard.

Who was I to judge? Sometimes I wondered what I would be when I grew up. Seemed like a reasonable dilemma on some level. So he chatted on at Starbucks, and the conversation was interesting and casual. The only thing that gave me pause was he was very flattering and kept mentioning how he was so glad we had met. As we were leaving, he asked me if I wanted to go with him to pick up his car. He chattered on about random topics. Then he stopped and said, “You look amazing, by the way. I love that sweater; what is it—burgundy?”

I responded, “I think its cranberry. Just a J. Crew item, nothing special.”

Not only was he flattering, but for any topic we discussed, he seemed to have the perfect anecdote. For instance, I mentioned an interest in beginning tennis. He was a good tennis player and would love to teach me. I mentioned I liked a couple of classes at the gym. He mentioned he was a kickboxing instructor, and he would love a new student. That class was also just around the block from us. This seemed a little too accommodating, but it was friendly.

We traveled to pick up his car, and on the way home, he asked if we could go out again, maybe for dinner or something more the next time. So far, so good. We left it that one of us would contact the other, and we would get together sometime. To me, “sometime” means sometime soon, but not necessarily in the same week. He seemed equally casual and lax about it, so it seemed fine. For the next couple of weeks, we would tentatively discuss meeting out for a drink or coffee again, but something seemed to come up either with work or home. Again, he seemed equally relaxed about this.

One night at home, I gave him a quick call. The weather had improved, so I’d decided I would see what he was up to.

“Hello. Oh, hi. How are you?” I started.