Starting the final Friday of my vacation, I began talking to a very interesting man on the mainland of Massachusetts. Right off the bat we clicked. Of course, I found him on Grindr, but that doesn’t mean he isn’t a man of quality.

I tried my hardest to convince him to visit me. I suggested we grab a drink and/or dinner. We went back-and-forth on the issue, and of course, I ultimately lost. No matter how hard I tried, he would not get on a ferry. Even after offering my bed following his question of where he would sleep, there was no convincing him. I went as far as to pull a shirtless picrture out of my arsenal. No dice.

But that didn’t deter me. We spoke every day of the rest of my trip. I enjoyed his messages. I enjoyed the cat-and-mouse game we played. When the time came to drive home, I turned to him to entertain me for the long car ride. We started messaging each other the second I hopped on that ferry. Had I been in charge of my own transportation, I would have made a detour on the way home, but that wasn’t an option for me.

Instead we took the oppotunity to get to know each other over five-and-a-half hours. I learned about his job as an elementary school principal. I enjoyed picturing him with a myriad of children circling around him. I remembered how much respect I had for my principal growing up. It was fun to picture the little tykes looking up to him. I learned he swam in high school and coached a team as well, but he had to give it up when he left the classroom for the principal’s office.

When we stopped at a gas station, I surprised him by calling for the first time. It was great to hear his voice. He never expected me to pick up the phone and call, but after talking to him for three days, I thought it was time to speak to him instead of just texting. The conversation was short, but it was special.

Once we got back on the road, it was back to texting. Periodically, I would switch back to some of the other guys on Grindr, but I didn’t have much interest in them. They lived in Rhode Island, Connecticut, etc. It was crazy enough I was trying to continue the conversation with someone in northern Massachusetts.

However, I learned one thing when I was working things out with San Francisco from across the U.S. You can find ways to make a long distance relationship work, but certain understandings need to be met. Both parties need to be willing to put in great effort to make it work, and an end game needs to be discussed at some point.

My mainlander continued to point out how ridiculous it was for us to be talking. He was very skeptical of the whole thing. I tried my hardest to get him to open up. I told him, “I’m not thinking about that bridge until I come to it. Right now I’m just enjoying chatting with you. Does it make sense to do this? No. But could it be something special? Only time would tell. But, it’s sure to fail if you don’t give it a chance to even begin.”

With every word, I found myself falling for what I pictured this man to be. I proceeded with caution, but I was also diving in full force to explore the possibilities of where our conversation could go.

When I arrived home, the conversation ended for the day. I was preoccupied with other men, but that doesn’t mean the conversation between us ended at that moment. I liked everything I was discovering thus far, but there was much more digging to be done…