I had been scheming for weeks, ever since I found out Smiles was screening his movie in the Hamptons in conjunction with the annual film festival. I finally had my answer – He wanted me there.

I had a wedding on Long Island the following day, so it was convenient for me to head out there early to catch his film. I hadn’t seen it yet, so I was very curious.

Since I already booked a hotel for the wedding, I wasn’t exactly thrilled about dropping more money on another hotel room (if I could even get one with the festival). Then I had a brilliant idea. My great-aunt has a house out in the Hamptons. I emailed my cousin and asked her if she thought I could use her mother’s house for a night. I wasn’t looking to make a whole weekend of it. We literally just needed beds to sleep in and showers in to use in the morning. Luckily, my great-aunt obliged. I asked Smiles if he’d like to stay with us, but I didn’t get a straight answer. He was trying to find something closer to the screening.

My roommate was my date for the wedding (sad, I know, but this is the life you lead when you’re gay and single). I ran my plan by her, and she was down for it all. I left work early Friday, went to Hoboken to picked up her car and our bags, drove back into the city, and pick her up when she finished work. After that, we headed up to Mount Vernon to hit up my great-aunt’s house to get the keys.

Of course, this took forever! We got turned around twice and had to deal with Friday evening city traffic. I was starting to fear missing the beginning of the screening. When we finally arrived at the house to get the keys, I couldn’t just grab the keys and run. I hadn’t seen my great aunt since the funeral of my grandmother, and it had been years before that since we last saw each other. I knew I would have to sit and chat a bit. She was thrilled someone was getting use of the house and gave me long instructions on everything. Luckily, she is still sharp as a tack and after a short chat, she suggested we get on the road quickly so we didn’t have to sit in too much traffic.

We made our way across almost the entire length of Long Island before finally arriving at the bowling alley the film was screened at. We didn’t even stop to grab dinner, so I was praying this place had some decent food.

We walked inside and were greeted by Smiles. He and his crew were getting set for a round of bowling. My roommate and I took over the lane next to them to bowl a game or two before the film. Apparently, we made excellent time and even had some to spare (Get it? Bowling… Spare…).

Smiles looked very smart and was being decently affectionate. I wasn’t sure how the night was going to play out. I had a feeling it may be slightly awkward, but I wanted to be supportive. I talked to him before heading out there to see what the situation would be. I asked, “Will you be working the whole time, or is it more relaxed than that.” He explained he would get to spend time with me, and it would be worth it for me to come since I was already heading out in that direction.

While we were bowling, the alley owner’s teenage boy was hanging out with Smiles and his crew. He’d been with them all day hanging flyers around town. At one point, he made a comment to Smiles about his wife coming to the screening. Smiles told him he wasn’t married, and the kid immediately questioned himself and said, “Or girlfriend?” When Smiles shook his head, the kid replied, “Oh, or boyfriend or whatever.” Smiles simply replied, “Well… Him,” and pointed at me. I didn’t notice this happening, but Smiles made it a point to come over and recount the story for me.

The time came for the crew to start getting set up for the movie. My roommate and I finished our game and hit up the bar to grab some drinks and grub. From across the room, I watched Smiles greet some of his friends and chat with them a bit. When he finished, he came over to check on me and grab a beverage. He mentioned his friends and their names. When he said one name in particular, my ears perked up. It was his ex. I was very curious how that would play out since I know they are still close, but rarely get to see each other. He told us to grab seats since the movie would be starting soon, so we made our way over to the chairs and grabbed a spot.

When he sat down, he sat with his other friends. I wasn’t jealous. I knew he didn’t get to see them much, so I would take a backseat on this one (however, a small part of me was very disappointed after driving over four hours to see this). I watched the movie intently, but I have to say, I did glance at Smiles and his ex in front of me to see the body language happening. Again, we weren’t in a relationship yet. We weren’t even dating yet. We were just seeing each other, or at least in my mind that’s how it was defined.

Part of the way into the film, I was shocked to see Smiles on the screen. I knew he was a producer of the film, but I had no idea he was acting in it as well. I was very proud of him and the great job he did. The film was great and surpassed my expectations — Totally an indie film I’d rent at Blockbuster, not some NYU student project.

After the film, my roommate and I made our way back to a spot at the bar to grab another drink. After chatting with his friends some more, he came over to me, apologized to my roommate and asked for permission to steal me away to introduce me to them. I’m sure my face lit up like a Christmas tree. He was acknowledging me to his friends. FINALLY! It was the validation I was looking for after the birthday party.

However, when one of the friends asked how we met, Smiles turned to me. My head immediately went to Grindr and how I didn’t want to say that. I could have said we met through a mutual friend, but I said, “I’m going to default to you on this one,” and turned to Smiles. He paused a minute and replied, “We’ve gone out to dinner a few times back in the city.” It was interesting to see him struggle with the answer as much as I had. After a short while, the friends had to be on their way. A band was beginning to play, so I called my roommate over and stood by her with Smiles and some of his crew. Later in the night, I learned the man I thought was his ex simply share the same name as his true ex. I felt a little more relaxed for some reason.

Periodically we showed signs of affection towards each other, such as a subtle hand hold or a glance. It was nice. It was still nerve-wracking because I didn’t know what he was comfortable with yet. We weren’t defined, so I wanted to make sure I didn’t overwhelm. That happened in the past, and I didn’t want it to happen again.

Smiles directed me to speak with the director of the film. She and her friend wanted to know if they could crash at the house for the night as well. This was the first conformation I received of Smiles coming as well. Until then, he hadn’t given me a definitive answer. I explained to the two girls, I hadn’t been to the house before and wasn’t sure of the bed situation. However, they were more than welcome to join the adventure. When the band finished, we made our way to my great aunt’s house.

The drive was nice and cut through some cute towns. When we arrived, Smiles said, “Do the Bouviers live here?” in a reference to Grey Gardens. The exterior of the house didn’t look to be in great shape. I was a little worried. When we got inside, I was pleasantly surprised to find the house in more than decent shape. It was very large and slept about sixteen comfortably. All the girls got their own rooms if they so chose. Smiles and I would be taking the master downstairs of course.

We immediately settled in. We talked a bit, and I came to find out he wouldn’t be able to grab brunch with us in the morning. He had to get the rental car back to the city by noon. I was very disappointed. Everything I planned so far had worked out perfectly. The screening. The house. My plan to make it a quick little getaway with him was failing. After brushing our teeth, we climbed into bed and cuddled a bit until we dozed off.

When we woke around 9am, I tried to get a little frisky. I reached my hand down and gently began to try to excite him until I was gently pushed away and told he was exhausted. I admitted defeat and disappointingly went back to just laying next to him. Me ego was a little bruised.

Shortly following, we both got out of bed, and he got dressed and packed up to go. I said goodbye to the bunch and tried to find something to entertain myself until my roommate woke up…