As I began to wonder if Best Boy and I could be more than just good friends with benefits, I tried to gauge where he was coming from at this point in our relationship. On Thanksgiving, I sent him a text to say:

When I think of all the people I’m thankful for this year, you are high on that list. Thank you for making a very tough time so much easier on me. It means more to me than you know. xoxo

I started thinking about how frequently our relationship dynamic had changed since May. Best Boy and I were friends for a while, while I was spending time with his best friend, Mr. Exec. After my situation with Mr. Exec had ended, Best Boy and I became friends with benefits. When I started pursuing a relationship with Mr. Agency, I stopped sleeping with Best Boy. That lasted for seven weeks until it was clear that Mr. Agency wasn't able to handle anything serious or monogamous. So then, I started sleeping with Best Boy again. (Are you confused? It's my life, and I sure am!) 

Throughout much of my relationship with Best Boy, I was recouping from biopsies, surgery or chemotherapy. I needed all the help and companionship that I could get, and Best Boy was there for me — a lot. Was he just there for me because we were good friends? Or, was he there for me because he had feelings for me beyond friendship? I didn't know the answers to those questions.

Dating in a traditional sense was incredibly difficult during treatment since there were weeks on end in which I didn’t feel well for a single day. If there were good days, they often occurred right before I was due to receive more chemotherapy. I wondered if it might be nice to go out on a proper date with Best Boy. I was curious how our dynamic would be if we tried to interact more like a couple. Would the comfort and caring that he had shown me so often inside my house translate if we were out in public?

After we returned from Silver Diner to satisfy my craving for Caramel French toast, I kissed Best Boy goodbye and said:

I should be feeling better starting next week. It might be nice if we went out at night for a change. Maybe Ceiba or something?

Best Boy: Okay. [Pause.] It’ll have to be next weekend, though. I have a lot of work projects and meetings this week.

Me: That’s fine with me. I should be feeling even better by then. I love having you over, but I also love going out with you. It's been too long since we've done anything beyond a little brunch. [We kiss goodbye again.]

I walked into the house with a smile on my face. Best Boy and I texted throughout the week, but the following weekend came and went without any mention from him about going out to dinner.

A few days later, Best Boy texted me, asking how chemotherapy had gone and if he could come over. I wasn't feeling well so we just watched a game on television. Best Boy talked about how much he had going on at the office so I didn’t want to disregard that it was a stressful time of year for him. I also wasn't in the mood to bring up the fact that we hadn't gone out to dinner. We feel asleep and had sex in the morning before the worst of the side effects hit.

Over the weekend, Best Boy came over again. He helped me out when I was too sick to do much of anything. I was so grateful for his help, but a part of me wondered if I had missed my opportunity to date him. Did I wait too long to realize what a great guy he was?

I wasn’t sure if I would see Best Boy over the Christmas holiday. We were both staying local, but he had a lot of family obligations that weekend. I had hoped for at least a call or text from him on December 25th, but that day came and went without him contacting me.

I had dinner with friends the night after Christmas. One friend commented how she was rooting for Best Boy.

Me: I had finally decided that I was, too! But, it might be too tough for us to transition to anything more than friends with benefits. He didn’t even wish me a Merry Christmas!

While we were out, the notification of a Facebook email from Best Boy came in on my Blackberry. The message said:

Merry Christmas! Hope you enjoyed yours to the fullest!

An email? A day after Christmas? On Facebook? Was he kidding me? I turned to my friends and told them the latest.

Me: I think there should be a rule that if you’re fucking, you should at least have to call and wish her a Merry Christmas on the day of! [My friends laugh and nod their heads in agreement.]

When I got home from dinner, I found myself more irritated than sad. I just sent Best Boy back a text that said:

A FB email?!? Really? Hope you enjoyed your Christmas. xoxo

He wrote back that he had been having problems with his cell phone. (And, yes, his Android has given him problems since he first got it.) I rolled my eyes at the text.

I had chosen Mr. Exec and Mr. Agency over Best Boy in the past. And, now I wanted to see what would happen if I just focused on my relationship with Best Boy. Had I missed out on the chance to do that?