If you’re just joining us, read Friday’s post before continuing…

The next morning, after only 3 hours of sleep, I woke and ran a few miles with D. I gave him the full debrief of what happened after he went to bed. He was very happy I was enjoying the new freedom I was allowing myself.

We got back and relaxed by the pool a bit. I texted Boston asking his plans for the day. He was heading to the beach after grabbing breakfast. Since the girls ate while D and I ran, we joined Boston and his friend for breakfast at The Hotel Breakwater. It was very casual and not awkward, however, I was fighting the beginning of a nasty hangover. Still I soldiered on. We discussed dinner the night before and all the stories that were swapped. Boston’s friend gave us all a new term to use referring to gays. “Pickle.” It was already part of my vernacular and fully utilized during my morning run and the remainder of my Florida trip.

We strolled down to the beach and met up with the girls. I hoped to get a minute to talk to Boston. I felt  we should discuss the night before because I didn’t want things to get awkward. I was very attracted to him but also valued his friendship. We never got to chat exclusively. We did, however, have a very candid group conversation with D and his girlfriend about sexual encounters, oral sex, semen, etc. I haven’t laughed that hard in a long time. I love how comfortable and open my friends are — like a breath of fresh air.

When we had to get on the road down to The Keys, we decided to take Boston and his friend to La Sandwicherie on our way out of town. His friend loved us. She asked, “Ok guys. Where’s our next vacation gonna be?”

Finally, the time came to say goodbye. We dropped them off near the hotel, and the best I got was a handshake reaching from the front seat to the back. I wanted at least a hug, but it would have been a full spectacle to get out of the car and do so.

I spent the next three and a half hours in a car with nothing to look at but wide open water. Of course, I texted with Boston the whole time. I was trying to be flirtatious without being overt. It seemed to be working… to an extent. I was having the conversation I wanted to have in person over text. Probably not the best solution.

Once we settled in at The Bahama House in Key West, D and his girlfriend went to the rehearsal dinner of a friend’s wedding. K and I were on our own for dinner. Halfway through, she scolded me to stop texting Boston. I obliged, but was in the middle of expressing to him my relationship with Broadway was over: It was just inconvenient timing to end it before my trip. He was worried that he was the catalyst. I reassured him I was having problems well before I met him, and he knew that.

We met up with the wedding party following dinner. Apparently I wasn’t the only ‘mo associated with this wedding. Everyone told me I needed to meet this great guy. Word to the wise. Not all gay men are compatible just because they are attracted men. While everyone told me we needed to meet, no one actually took the time to introduce us. This is partly my fault because I insisted I get more lubricated before I speak to him, but once I was relatively tipsy, no one made the effort.

The next night D and his girlfriend went to the wedding. K and I found a spot for dinner. At this point I curbed my texting to Boston. D’s girlfriend started texting me about the ‘mo at the wedding. She told me he was anxious to meet and we should meet them when it was over and all go out. When we arrived, he and I were finally introduced. It couldn’t have been more awkward. After a few minutes, he excused himself to go chat with friends. I have to admit, while not interested, my ego was a little bruised.

When the time came to head home, I was trying to coordinate with Boston if we would be traveling along the same route at any point. We were flying out of the same airport and his connection took him through Newark, where I would be landing. I called him to get details and tried to work it out for me to swing by their gate at the airport. Timing never allowed for it.

Days later, Boston and I were skyping. That day, I was psyching myself up to ask him out on a date. I knew it was a dumb idea since we lived in different cities, but I also didn’t see why I shouldn’t give it a shot. After chatting for a bit, he was ready to sign off. My window of opportunity was closing. I asked him if I could take him to dinner sometime. He responded, “Yea. Let me just hop on my private jet.” To which I responded, “There’s no reason why I couldn’t visit Boston some time.”

This was followed by a looonnngggg pause. I could see how uncomfortable the proposition made him. However, he graciously responded, “Sure. I’d be down for that.”

The potential of this was exciting, but certainly more one-sided than I had hoped. After talking with him more, I realized a relationship was never going to happen. At that point, I was able to step back from the situation and realize he was a much better fit for the “friend zone.” I stopped my advances and started talking to him like a true friend, and that’s when I started getting more positive feedback.

When a business trip would land me in Boston, I had the opportunity to make good on my proposition for dinner, but that’s another post for another day.