Posts Tagged family
Since deciding to end things with Smiles, I’d already been on one date and had one hookup. I certainly hit the ground running. I felt slightly guilty all this was going on before we even had the chance to formally end things, but then again, things never really formally began between us.
I wasn’t wasting any time either. I had been talking to a really nice guy on adam4adam.com and set up a date to grab drinks with him after work Friday evening. It was a bit awkward because this was truly a blind date.
He had two pictures on a4a, but neither was clear and one didn’t include a face. When I asked him to send me a better face picture, he told me he didn’t like taking pictures of himself. Of course a red flag raised in my mind, but I had nothing to lose either. If I arrived and the guy was unacceptable, I was right next to the Port Authority bus terminal. I would be home in no time with little of my time wasted.
We agreed to grab drinks at Arriba Arriba in Hell’s Kitchen. It was conveniently located between his apartment and my office, and like I said, it wasn’t far from my transportation hub to go home.
As I left my office and began walking north, I was quite nervous. I’d never been on a true blind date before. I’d at least seen pictures of their faces, but this time I had no idea what he looked like. I joked with him, “Not gonna lie. Not sure what you look like… Haha.” It didn’t take him to respond: “Sorry mate. Don’t like taking pictures of myself. We will find each other… haha. You can ask me to leave once you see me and how ugly I am. Lol.” I didn’t care all that much at this point for the picture. I was already going in blind. I replied, “No apologies needed. Just tellin’ ya you’re gonna have to find me…”
I waited for him on the street corner. I put that time in a good location to good use. I surfed Grindr in HK for any new prospects. I know some may say that is classless considering I was waiting for a date, but I’m not in HK all that often anymore, and there is more talent in that neighborhood than where I work. He finally arrived and approached me. I asked how his trek to HK was, and we went inside to find a table.
When we learned we could only stand at the bar since we weren’t ordering food, we decided to go elsewhere. I was at a bit of a loss because I hadn’t been in the neighborhood for some time. I didn’t know of a good place for us to go for a drink. Luckily, this guy was good on his feet. He suggested Eatery, and we were off.
We grabbed a seat at the bar and ordered a few rounds of drinks. We chatted for a long time about a myriad of things. The whole time, he kept his ball-cap on. Beyond the fact that he should know it’s bad manners, especially since he was an older gentleman, I was also worried there may be no hair under there. I’m not shallow, and looks are not everything to me. But, if he was balding without shaving his head, I wasn’t sure I could deal with that. (Smiles shaved his head and I was obviously okay with that).
We talked about our upbringings. He lived a bicoastal lifestyle, living in California and South Carolina. He also was shipped off to boarding school in Switzerland, where his grandparents lived. I grew up on a farm and went to public school. We had quite the education/socio-economic divide before. This is one thing I‘m not sure I am capable of getting past. I’m sure if it was the right guy, I could handle him coming from wealth, but it’s something that makes me quite uneasy. He came from money, and a lot of it.
I also learned he leads a very lavish lifestyle. He told me about his plans to purchase a house in Barcelona. He’d recently traveled there to scope out some places. He also told me about the $200,000.00 loan he gave a friend and was never paid back because the friend died and left his only possession, his apartment, to someone else. He told me about his lavish trips to the Caribbean islands recently. The list goes on.
Ironically enough, he wasn’t talking about all these because he was trying to impress me (Or at least it didn’t come off that way, which is fine). It simply came up in conversation or I coaxed them out with questions. I just felt uncomfortable with our socio-economic differences. I don’t really aspire to the position of kept man. I want someone who will share the financial burdens with me equally. I know a lot of people would love to find someone rich to marry, but money means very little to me when it comes to love. I think like I would constantly feel like less of a man if I had everything provided for me constantly, and I contributed far less to the relationship. Maybe this is something I will learn to get over in time, but for now, it makes me uneasy.
I learned how he continued to build his wealth and his professional relationship with a family in Canada. He told me about all the businesses he was involved in, and I started to worry he was another Smiles — Too much on his plate to commit to a real relationship. I also learned he wasn’t out to many people in his life, even after he’d been in a nine-year relationship with a man who left his wife for him. It ended when the man cheated on him while he was away on business. I wasn’t sure how I felt about him still being in the closet. He’d experienced too much and was far too old to still be in denial of his true self. I wasn’t sure I wanted a “project” at that age.
Drinks quickly turned into dinner. We stayed at the bar and made friends with the waitress. She was super sweet and very interested in chatting with us. Over our meal, we conversed more, and I learned we share a lot of the same morals and interests. We had similar outlooks in life.
He also became much more physical as the night progressed. He constantly had his hand on my leg rubbing my thighs and caressing the back of my knee. I started to do the same. Periodically, he would stand and give me a big ol’ bear hug. It was sweet. I liked knowing he was a passionate physical man. I needed that after Smiles constant distance.
Six hours later, we were ready to leave the bar. He decided to walk me to the bus. I thought when we exited the restaurant we’d exchange a kiss and go our separate ways. He was a true gentleman and walked me to the Port Authority. Not only that, but he walked me to my gate to wait for my bus and stood there waiting with me. It was midnight, and he was being a total sweetheart. He stood anxiously next to me as if he didn’t know what to do or how to close the date. He wasn’t really out, so I had a feeling a goodnight kiss in front of a large group of strangers was out of the question. When my bus arrived, he said goodbye and we agreed to be in touch.
As I rode home from the date, I wasn’t entirely sure what I thought of him. He became more attractive as the night went on, but I wasn’t sure if that was his personality or the alcohol stepping in for average looks.
I had a lot to think about. It was clear to me he was interested in me. The next day, he texted to see if I was interested in catching a movie that evening. I told him I had plans to hang with friends locally, but if they fell through, I’d let him know. When I decided to keep my plans, I texted him to let him know. He wasn’t all that concerned considering he had hopped on a flight to Boston to hang out with friends and go to a party. Yup, hopped on a flight that day. He obviously didn’t have a planned flight considering he asked me to go to the movies — Unless he was planning to fly me to Boston to do so…
That night, while out with my friends, I called Boston. He told me some of his new exciting war stories, and I told him of my trepidations about Deep Pockets. He told me I was nuts to write him off based on financial differences, so I decided to see where things went over the next week or so.
We texted a few times more, but interest wasn’t strong on either end as the text messages slowly came to an end. I was on to the next prospect…
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Christmas day had passed. My time home was coming to an end. I was happy to be home, but I was also anxious to get back to normal life.
The morning after Christmas, my father and I decided to do a little shopping to see if we could land any special deals to kill time. I would also finally be in cell phone service, so I could text Smiles and wish him a safe flight. When I got into service, I got an influx of text and picture messages. He’d sent me quite a few, keeping me updated on what he was up to. I really was missing him and quite anxious to get back to see him. I proposed we do dinner at my apartment since he had to postpone it before the holidays. He texted back in agreement. I was finally going to get to make us the standing rib roast. I told him I missed him, and he responded, “I miss you too! 🙂 “ I could have melted into a puddle right there. This was so unlike him to express his emotions like this, but I was eating it up!
The day after Christmas is always spent with my father’s side of the family. We all gather together for a nice potluck meal that rotates from house to house year to year. This side of the family has also shrunk significantly. My grandparents have been gone since I was quite young. My father’s brother is in rough shape these days from his battles with diabetes. His sister died a few years ago and her husband is in a nursing home. I rarely see their daughter, my cousin since she moved away and got married. That left one sister whose husband also passed away a few years ago. But as that generation was shrinking, another was growing in leaps in bounds. The living sister has 5 children, all of which are married and have become baby making machines. They now outnumber the four of us five to one.
The gathering is always a lively one with many children running about. Christmas is one of the two times I spend with this side of the family each year (the other being an annual family reunion). We also have an annual tradition of a “Yankee gift swap” or “white elephant sale” depending where you come from. The tradition has lost a lot of its allure as my cousins have adopted a new tradition of buying crap at Wal-Mart and Big Lots the day after Christmas for half price.
My sister and I had to work the Tuesday after Christmas, so around 5:00 we hopped in the car and made our way back to Hoboken. When I got back to my apartment and unloaded all my presents from home, I picked up the phone and called Smiles. Sadly, it went straight to voicemail. I was hoping to relax after a long car ride with some time talking to him, but alas, that wouldn’t be the case.
My roommate arrived home, and we swapped all our holiday stories. We plopped down on the couch and started to catch up on the programs we saved on the DVR. After some time, Smiles called. I think if you were in New Jersey when the phone rang, you may have seen a beacon of light in the sky that was my smile.
He told me about his trip home and the ordeal he went through. When he got back to the city, he’d gone out with one of his female friends for dinner. He devised a new plan to work out of her apartment going forward so he would be more productive than he was working out of his apartment. He felt if he had a place to go to every day that wasn’t in line of sight of his bed, he would get more done. I told him I thought it was a great idea. Even though they wouldn’t be coworkers, they could keep each other on task. Either that, or it would be a complete disaster, and they would be a constant distraction for each other.
I told him about my time home, my family and how the gift swap has become a sham. He laughed and told me about the rest of his time home with the family.
It wasn’t a long phone conversation, as our phone calls never are, but it certainly satisfied my hunger for Smiles. It would satiate me until I got to see him the following night when he came over for dinner.
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Christmas Eve, my family and I always go to mass. We wake Christmas morning and open presents, so we go the night before.
Every year when we get home, it’s a tradition for my family to take a picture in front of the tree. I am always the obligatory photographer, which for some reason I strongly resent. Everyone in my family has a point and shoot and knows how to set up a tripod and click a button. I’m not exactly sure why it is my duty just because I’ve taken photography classes. I digress…
We take the family portrait and make our ways to our separate rooms to take off the Christmas outfits and get comfortable for the rest of the night.
My father and my sister wanted to watch a football game, and my mother and I had no interest. I can’t for the life of me remember what we decided to watch, but we were in the family room while the other two were in the living room watching the game.

Somehow my mother and I got back on the topic of church and the changes to the mass. For those non-Catholics out there, the Vatican altered the verbiage used in the mass this year. Apparently when they originally translated the mass, they messed up. All of a sudden they felt the need to “fix” it to be truer to the original text. I was arguing the changes weren’t necessary. The changed things like the following: The priest says, “Peace be with you.” In the past the congregation responded, “And also with you.” Now, the response is, “And with your spirit.” To me, those changes are semantics.
My mother heavily disagreed. She felt the changes were necessary and good. She felt it helped her pay closer attention to the mass. To me, it was a distraction. I was now paying more attention to a piece of paper I had to read than I was to the mass. My mother asked me if my priest had been explaining the changes, and somewhere I slipped up. It became apparent I hadn’t been going to church every week.

My mother got heated about that issue. “You haven’t been going to church every week, have you? But you had no problem receiving communion tonight!”
My sister and I had discussed religion and my status as a gay man on numerous occasions. I told her there was going to come a point where I told my parents I don’t want to go to church anymore more. She asked that I hold off on that for a while. I told her I wasn’t going to bring it up anytime soon. I wasn’t going to bring this topic up, but when my mother brought up this topic, I was gonna go with it.
“Really, Mom? Really? That’s going to be the reason I don’t go up to receive communion?” I quipped. “What do you mean? she said. “I mean, not going to church is going to be the reason I don’t get communion, not me being gay?” I responded.
My mother voiced her opinion that being gay is not a sin. Not attending church is a sin. I pointed out to her that both are sins in the eyes of The Church. She tried to convince me The Church’s stance on homosexuality is based on decisions made by men, and not attending church goes against a God-given law in the commandments. I pointed out to her the commandment to honor thy wife. (I know my argument is flawed here because the commandment refers to adultery). She sighed a bit because I did have a point in her mind.
“Well then everyone who’s ever had premarital sex shouldn’t be receiving communion either,” she added. “Exactly! That’s exactly what the Catholic Church believes,” I told her.

“Well then I shouldn’t be receiving communion because I’ve used birth control,” she noted. “Exactly. If you don’t believe birth control is a sin, then you’re not truly Catholic. You’re Catholic lite,” I exclaimed. “I have never been a true Catholic. I’ve always been a ‘cafeteria Catholic.’ I pick and choose what I want to believe. That is what religion is. It’s personal. I don’t always need to go to a specific building with a specific man to have a relationship with God.”
“You’re not going to church because you’re lazy, not because it’s against something you believe,” my mother accused. “I don’t want to be a part of an organization that doesn’t want me to be a part of it. It’s insulting. I am a man of convictions,” I defended.
“Then why go at all?” she asked. “I go because sometimes I want to go. Sometimes I want to be in church and among other people. And, sometimes I can’t get over it, and I decide not to go. But, that’s my choice. Religion is personal. So maybe I’m not a Catholic, but I am still a Christian. And, I still believe in God.” I declared.
My mother wasn’t happy with this. She was raised staunchly Catholic, and it’s been a part of her entire life. She didn’t see my side of the argument at all, but it was clear it was upsetting her. She had been crying during the conversation, and she’d had enough. She said, “I need to go to bed,” and turned to leave the room.
I walked into the other room with my father and sister. My dad asked, “Did you chase your mother to bed?” I told him, “She wanted to talk about God and gays. You can see how well that went. I wasn’t going to bring it up, but when she did, I wasn’t going to avoid it.” With that, the subject was closed.
I felt bad she got upset, but I was honest about my feelings. It’s how I felt. I really wish it wasn’t how we spent our Christmas Eve, but it had to happen sometime. It wasn’t a positive conversation, but at least the subject was broached, and at least we were having an open dialogue.
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Smiles was halfway across the country and Christmas was rapidly approaching. There’s something about dating someone over the holidays that makes you really appreciate that person. There’s also something to be said about being single over the holidays that makes me utterly depressed. I was happy to be on the dating side of the fence this year, but I would certainly miss Smiles.
While he was home, he sent me periodic texts out of the blue. I got a few picture messages of him and his mother’s dog on the beach and some pictures from around town. They were sweet simple texts that showed me even though he was many states away, he was still thinking about me throughout his day.
This seemed a bit of a stark contrast to the conversation we had just before he left. He told me he couldn’t be in a serious relationship right now. If that was the case, why was he reaching out to me even when I wasn’t around. I started to wonder if maybe he didn’t know what he wanted.
As he was driving around, he called me to chat. It was a really sweet conversation. He was asking how I was doing and what I’d been up to since everyone left town ahead of me. He was telling me all about where he grew up and his old high school. We talked about his mother a fair amount and her business. He sent me a picture of some of the things she worked on.
I was getting access to mother information. You don’t share that with someone you don’t truly care about. I was getting more of him. It was exactly what I wanted. I wanted to know more about where he came from. I wanted him to open up. I wanted it all.
Maybe my conversation sparked something inside him. Maybe he realized he wasn’t appreciating me as much as he should, but there certainly was a stark difference between the time we spent together before the conversation and the time following.
As the rest of the family was arriving into town, Smiles started getting anxious. This is something he did regularly — Got worked-up over small things. He was texting me about solutions to the problem, such as drinking. I encouraged him to do whatever made him comfortable. There was no reason he couldn’t have a few cocktails to take off the edge if it would make him more relaxed. He was anxious about talking about his career. He was still working hard to get it off the ground, and I think he was ashamed about that. I told him he needed to be proud for being so brave for starting something from the ground floor. Not many people can do that. They just go work for someone who has already done all the heavy lifting. He has very low self-esteem when it comes to his job, and he has no reason to. No one finds overnight success, and I have strived to convey this to him constantly while being very supportive of all his ventures.
I think my pep-talk worked because his texts became more light-hearted and relaxed. Either that, or he took my advice with the cocktails to a much higher level.
The morning my sister and I were driving home to Pennsylvania, he texted just to see how my day was going. Again, I love these sweet gestures that show he’s thinking about me. I was much happier over the past few days than I was immediately following our conversation.
When I got home, I had no cell phone service. It makes it a little more difficult to talk without a little more effort. I made sure he had my parents’ landline number, but I knew he wouldn’t call it. He probably didn’t want to have to talk to anyone if he called and they picked up.
I had his number, but now I was settling in with the family. I wasn’t home for long, so I wanted to make sure the time I was there, I was present. I didn’t want to be running off constantly making phone calls.
It was Christmas Eve, and I was off to mass with my family. I texted him on the way to say hi and let him know I was thinking about him.
When I came back out of mass, I had a response. He told me he dodged the church bullet. I told him I wasn’t so lucky. My parents’ priest is one of the most boring people I have ever encountered. Going to church is penance in itself.
I wished him a Merry Christmas Eve just before driving out of cellphone service. We were on our way home to take our annual family Christmas photo before relaxing for the rest of the night in front of the TV…
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Waking up with the feeling of dread is never a good thing. Upon opening my eyes, I immediately knew something was wrong. It all came crashing back. I remember the conversation I had with Smiles the night before in my bed. It didn’t go as well as I would have liked it.
I needed to reassess the situation and make a decision before proceeding. One thing was for sure; I was going to proceed with caution. No longer was I going to invest so much of myself into a one-sided relationship. Smiles was still interested, and I had optimism the relationship could still progress towards something good. However, I could no longer devote so much of myself to someone who wasn’t doing the same for me.
I had that day off, but I had to wake very early. I needed to get my friend’s car keys before he went to work so I could take Smiles to the airport. When I volunteered to take the day off from work, I thought it would be a perfect way to see him off. I wanted to be both helpful and selfish. I wasn’t going to get to see him for a week, let alone on Christmas. The next best thing I could get was sending him off at the airport.
I climbed out of bed, put on clothes and rode my motorcycle over to my friend’s place. I swapped the bike for his car and drove back to my apartment. When I got back to my room, there were a few minutes left before Smiles was supposed to wake to get ready for his flight. I undressed and climbed back into bed.
Since we went to see the stage-show the night before, and he was working through the day before, he wasn’t able to pack yet. When my alarm went off, we woke and got ready to make our way into the city so he could pack.
I drove him through the Holland Tunnel and stopped in front of his apartment. There were no legal spots available, so I had to sit in the car while he got ready. When he got out of the car, Smiles checked out another street and texted me from his apartment: “If you wait another five minutes, you can park on the other street at the meters.” It was nice of him to check that out so I wouldn’t have to sit in the car alone the whole time.
I joined him upstairs and tried my best to assist. When he was ready, we got back into the car and set off for the airport.
My question from the night before was still in the back of my head. The car ride was rather quiet. It was as if we were both searching for something to talk about. I had yet another question burning a hole in the back of my mind. I had no New Year’s Eve plans, and all my friends did. I didn’t want to spend it alone, but Smiles hadn’t mentioned it to me. I had no idea what his plans were, but I wanted to spend it with him. The conversation from the night before didn’t change that. I was about to ask him if we could spend it together, but as we neared the airport, things got hectic because he wasn’t sure which terminal he was flying out of. That question would have to wait until later.
Once we had that settled, I found a space at curbside and helped him unload. We exchanged a very quick hug and kiss as he set off for home for the holidays. It was very unceremonious. I don’t know if he was self-conscious because we were in public or if it was because he still felt awkward, but I was very disappointed. That was not the way I wanted to be kissed by the man I was dating but not seeing on Christmas. That was not a proper goodbye.
As he walked away, he turned back and said, “I’ll call you later tonight.”
Since I had my friend’s car and the rest of the day off, I decided to run an errand I’d been neglecting. I took a route home that allowed me to stop by Michael’s to pick up a large panoramic photo I had framed. All that alone time is NOT good for me. It’s a sure to produce over-thinking and slight depression. I really didn’t know how to proceed. There was a fork in the road, and I wasn’t sure which road to take.
I decided to make a stronger effort to engulf myself with my friends. I wasn’t going to give so much of myself to Smiles, and in turn, I would fill that void with friendship. After I ran my errand, I went home and watched TV on the couch. I needed to distract myself with some form of entertainment, but it wasn’t working. I was still thinking about what I was going to do. I hopped on Facebook while watching TV and got a message from N: “I miss you buddy.” I hadn’t hung out with him since we broke up with the exception of my holiday party. Maybe it was time to give friendship with him another chance. I hit him up to see what he was up to. He was going out that night and told me he would keep me in the loop regarding his plans so we could hang out.
I know Smiles was settling in the with family, and I wouldn’t expect him to call. But, it would be nice if he called, even if just to let me know he landed safely. That night, I never heard from Smiles…
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Still thrilled about a spectacular weekend with Smiles, I began a new week.
Monday passed by without me seeing Smiles again. I did speak to him however. We spoke while I walked home from work. He still had a migraine, and I tried to console him. I wished there was something I could do for him, but I was powerless.
He had a work event that evening, so he soldiered on. His migraine was lessened, but he still wasn’t 100%. I knew it was going to be a long night for him.
He called when the event was over to say hi and check in on me. I always relish his phone calls just to say hi and ask me about my day.
I explained to him I was watching the first Twilight movie. It happened to be on TV that night, so I made it a point to watch in an attempt to catch up to the current day release of Twilight: Breaking Dawn pt. 1. I was also able to find the second and third installments in the series on the guide over the next few days. Smiles seemed excited to see the movie, so I was putting in the effort to get onboard. I have to say, they’re certainly not amazing cinema, they’re not unbearable either.
I asked him to wait to see the movie together in the theater. He agreed. After talking about the series, he realized he’d never see the third installment, Twilight: Eclipse. I told him I would keep it on my DVR, and we could watch it together before hitting up the newest in the theater.
We were also coming up on Thanksgiving. I struggled with the thought of inviting him to come home with me. He is from and his family is still in Florida. I knew he wasn’t planning to go home, but I wasn’t sure if he’d have other plans. The thought of inviting him came from numerous places. I felt we were comfortable with each other, and I knew he would stand well with my family. He was very good at getting along with strangers, and I knew he could win them over, especially since this would be the first time they’d learn about my homosexuality. I knew it would have been a little early in our relationship to ask him to come home with me, and this is the main reason why I didn’t. I didn’t want him to think I was a little psycho.

In the meantime, I learned he finally did make plans for Thanksgiving. He was going to a few friends’ homes out on Long Island in the Hamptons and on Fire Island. I was happy he found some special people to spend the holiday with, but was a little disappointed I wouldn’t be spending it with him.
Before I went home, and he split for Long Island, I wanted to see him again. I suggested we grab coffee or something quick because I knew he would be quite busy with work leading up to our departures on Wednesday. He told me we’d have to play it by ear, but he would make a concerted effort to work it out.
I was worried I wasn’t going to see him before the long holiday weekend. We’d spent other weekends apart, so this shouldn’t be that big of a deal, but to me it was. I wasn’t spending the holiday with him, so I wanted the next best thing.
Tuesday evening I had a dermatologist appointment to have an ingrown hair taken care of. We were going to attempt to meet after as long as time allowed for it in his schedule.
It turned out he was able to meet. In the rain, I made my way to Lyon to grab a drink with him before he was going out to dinner with business colleagues who were in town for the week.
This was the first time I’d see him following a workday in which he interacted with clients. He looked very smart and super cute. It was all I could do to keep my hands off him. He was happy to see me, but I could tell he was pretty exhausted from a long day. We ordered some small dishes because I was ready for dinner, and his dinner wasn’t until 10:00 or 11:00. The conversation was nice, and we discussed our plans for the weekend. He also expressed concern for the incision on my abdomen from the dermatologist. When we finished, we paid the bill and began to walk towards the PATH/his subway.
We popped into a fun travel amenities shop to check out some of the cool things we noticed in the front window.
We walked a little further and reached his subway. He began to descend the staircase, and I called after him to explain I wouldn’t be joining him since it didn’t take me near the PATH. He walked back up a few steps and gave me a quick kiss as he said goodbye.
It was very unceremonious and not very romantic, but I decided to concentrate on the fact that I got to spend time with him at all before he left.
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First, I am thrilled to announce I am the new and proud owner of the domain onegayatatime.com. I feel so legit now! Please share the link with your friends and family and anyone whom you think might be interested in the content I write. You can also find me on Facebook, OneGay AtaTime, and you can follow me on twitter @onegayatatime. If you’d like to contact me directly as some readers already have, my new email is blog@onegayatatime.com. Enjoy!
Secondly, I hope you are all having a very special Christmas Eve! Warmest wishes to you, your families, and the loved ones you have the privilege to share the holidays with.
P.S. Don’t forget to abuse the mistletoe.
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Over the next few days, I thought a lot about my relationship with Smiles. It was a constant roller-coaster. As far as relationships go, I am an infant. I’ve had all of five real relationships in my life, including this one. I was still learning how to be in one.
I needed to clear my head. For three days straight, I woke up early to run. It was the perfect way to start my day, I allowed me time to think without really being distracted, and I was able to work towards my spiteful goal of losing my pudge as Smiles so gently pointed out.
It was also beginning to be quite a busy week for me at work. Tuesday I worked until midnight. I talked to Smiles that night when I had a break to make dinner plans with him for the following night. Since I started dating him, I purchased a lot of Groupons for restaurants, so I thought it was time to start using them up. I was eating out at restaurants a lot more than I would have if I weren’t dating Smiles. This was the perfect way to lighten the blow to my wallet. As I left work, I texted, “Dinner tomorrow night maybe? Just leaving work (12:00) :(”
It wasn’t until the morning when I got a response: “Morning! Just getting this. I went to bed early last night. Dinner tonight works.” I explained the Groupon I purchased for Philip Marie in the West Village and asked him if he was okay with the choice. “Sounds good if you get off before 12!” he replied.
Later that Wednesday afternoon, Smiles called to make sure I was still getting out on time, otherwise he was going to grab dinner with some of his friends. I got where he was coming from, but it also felt a little like he was trying to get out of our date. I assured him I would not be working late. As the afternoon progressed, he asked about what time we’d meet, joking about “a blue plate special at 6:30” when I told him I’d be done around 6:30/7:00. We made plans to grab dinner at 7:30. I took the opportunity to slip a joke in there about his grandpa status and his ability to make it until 7:30, and he retorted by saying, “I’m stressed. It makes me sleepy. I’ll bring my cane.”
We sat in the front window of the restaurant, and after we ordered drinks, we dove into conversation. We talked about family and career goals among other things. He talked about his desire to be beyond financially stable so he could spend more time with his family. He is not originally from the Northeast, so spending time with his family isn’t the easiest or most convenient. He also talked about his desire to build an empire. He is very passionate about a lot of different business ventures, many of which are sound ideas. However, sometimes I worry he tries to take too much on his plate at once.
The conversation was great. It was a conversation two people in a relationship would have, not two people who were just dating. I joked with him, “You’re going to be the next Nate Berkus.”
Oooooo, did I get a look! Apparently, Smiles met him in the past, and isn’t the biggest fan of him as a person. “Okay. Note to self: Don’t equate you to Nate Berkus ever again,” I said with a smile.
When the waiter came to ask us about desert, Smiles started a conversation with him like he always does. He asked if we were his only table, and the waiter described his other table. It was a man and a woman who he suspected were on a first date. We joked about our date. While we weren’t on a first date, he was learning all kinds of new things about me, such as my penchant for Black Friday shopping. He took the opportunity to take a few playful jabs at my sanity while we all had a good laugh.
After we paid our bill, we started to walk the five blocks towards the PATH. Instead, we walked about eight blocks. That was about the time Smiles realized we’d gone too far. He questioned the situation, but I explained how I was enjoying the conversation and was willing to walk back up to the PATH if I needed to. We were standing in front of a liquor store while he finished the story he was telling. When he finished, I grabbed his jacket and pulled him in closer so I could kiss him. For the first time, I felt like we were really kissing. We exchanged many affectionate kisses before finally pulling away from each other.
At that point, he said, “Why don’t you live in the city?” I laughed and replied, “Was that a subtle hint? I’m not that far!” And with that, I walked away with a smile from ear to ear. I finally felt like we had moved beyond going on dates with each other. We were dating. We were in a relationship, and I was very happy!
When I got back to Hoboken, I sent a text, “You make me smile 🙂 .” Shortly following he responded, “That’s a good thing cause I ain’t so easy to like all the time!”
I was REALLY HAPPY with everything that night. I was getting the validation I needed. I was also looking forward to Friday. That was the first time I’d be able to see him next since I play volleyball every Thursday. That would also be when I would once again attempt to seduce him and attempt to roll around with him in bed…
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As we left dinner Saturday afternoon following the opera, we began to walk north on Columbus Ave. I had no idea where we were going or what we were about to be doing, but I had a feeling I was going to enjoy the surprise. I was already enjoying the fact that he was being romantic enough to surprise me.
Finally we stopped at the corner of 67th to pop into 67 Wine. Call me stupid, but I was in the store for a solid two minutes before I realized what his plan was. I heard Smiles ask for a cold bottle of white wine, but it wasn’t until he asked for plastic cups that I realized his intentions. Apparently he wasn’t ready for our date to end. We were a few blocks from Central Park. He must have been planning a spontaneous picnic.
It’s been a looonnnggg time since a man put that much thought or care into a date with me. I was swooning from the attention. As we walked to the park, I had a smile from ear to ear.
We passed a family with a child being slightly rambunctious, and he stated, “Yea. The jury’s still out on that one.” I didn’t let that comment fall too far before I scooped it up. On our second date, he pointed out an apartment that would be perfect for two edgy gay men to live in, implying no children. I know children is the last thing one should be thinking about on a second date, but the comment caught me off guard. Children are definitely something I want in my life at some point. Hearing that he’s still entertaining the idea was reassuring. I said to him, “What? Kids?” When he acknowledged, I pointed out how he’d be a great dad.
We entered the park by Tavern on the Green. As we walked out onto Sheep’s Meadow, there was a plethora of people out enjoying a spectacular October Saturday. There were lots of frisbees and couples, much like Smiles and I, enjoying a nice evening in the park just as the sun was setting.
We found a plot of dry grass in the middle of the open field to sit and crack open our wine. He poured each of us a glass. I sprawled out a bit and leaned back onto my elbow to get closer to him to chat. It was really shaping up to be a very special day. A day a few hours earlier I wasn’t sure would come to fruition.
Somehow we got on the subject of high school hookups, which was very interesting to hear him talk about it. When he was in high school, he dated girls exclusively, as did I. I liked that about him for some odd reason. It made him a little “less gay,” if that makes any sense. He talked about his first time. At one point, after one of his stories, we even joked about Saran Wrap being used as a contraceptive. I talked about my upbringing and family. I learned my suspicions of his parents’ divorce were true. The conversation continued though college, finally ending in the real world post college. I found out when and where his love of cars came from (He owns a Mustang from the 60s I’m dying to take a ride in… Among the other things I want to do in it). I learned a great deal about him amongst those blades of grass. I caught a glimpse into how he became the man he is today.
As the sun went down, some cuddling ensued. It wasn’t until we couldn’t see very far in front of us that we decided to leave the park. After a short pit stop at the restrooms to relieve ourselves, we made a detour to investigate where some loud drumming and music was coming from. We discovered it was an impromptu drum session/dance party the broke out in the middle of the park. We stood and observed the celebration for some time, before out of nowhere, Smiles jumped into the mix and started dancing with one of the women. I loved his spontaneous spirit and was VERY impressed with his dancing skills. I was a little taken aback actually. I couldn’t stop smiling. I wasn’t sure if he expected me to join in, but I hadn’t had enough to drink yet to get my ass in that dance circle.
When we had our fill, we walked down a darker pathway. I took the opportunity to pull him aside for a quick kiss. I laid a big one on him. We continued on towards Columbus Circle without further plans. When we neared the subway, he pulled me towards him and said, “So I have a suggestion. Let’s go back to your place, put on gym shorts, and sit on the couch and watch a movie for the rest of the night.” My face lit up with a smile, and I said, “That sounds like a spectacular idea!” With that, we made our way to Port Authority to hop on the bus.
When we arrived at my apartment, I was surprised to find my roommates home with a large group of girls smoking on the balcony after a bar-be-que. I was less than thrilled. Our night of sitting on the couch alone was going to be heavily interrupted by a pack of young girls.
We poked our heads out on the balcony and said hi before heading to my room to put on more comfortable attire. Of course some kissing and heavy petting ensued while in my room, but we made our way back out to the balcony. Smiles planted himself in the middle of the group as if he’d known them forever. He joined their conversation and gave them advice while we all smoked. When Smiles and I had our fill, we went inside to order take-out to satiate our muchies. While waiting for the food, Smiles beckoned me to my bedroom. He was hungry for sex. After the day he showed me, who was I to deny him that pleasure. And, I too was hungry for sex.
However, if you’ve read my blog, you know I prefer to top. There was a polite standoff for a short period as to who was going to hold that position. No words were said, only body positions exchanged. Finally, I found myself in a weaker position and was conquered. If you’re keeping track now, that’s two points for him, none for me. I was okay with letting him top this time, but next time was definitely mine. This wasn’t something we discussed, and I wasn’t sure how to bring it up. I wanted to make sure he wasn’t exclusively a top, but I wasn’t ready to end it even if he was. It was a catch 22.
Warning: The following may be a little graphic for some. After some passionate time, he finished. He was continuing, waiting for me to finish. I explained to him I never finish from bottoming. I was insinuating that I normally top. I wanted to make sure he didn’t think I always liked being on my back. He understood what I was saying, but was a little shocked I never finish from bottoming. He was perplexed. This was twice now we were together where he finished, and I did not. This topic is worth a blog post on its own. Stay tuned…
We cleaned up and went back out to the kitchen just as the delivery man was buzzing. We took our food and plopped down on the couch to eat. As we settled in, the girls finally left the apartment. We decided to watch the second Transformers since Smiles had never seen it. I was happy just spending time cuddled up next to him. Being as it was a long day, I kept falling asleep on him — Literally on him. No matter how hard I struggled to stay awake, I continued to fall asleep. When the movie was ending, I awoke and felt really bad for sleeping on him.
We cleaned up our mess and made our way to the bedroom to settle in for the night. I had one of the best days I’d ever spent with another man. I slept with a smile from ear to ear that night.
When we woke in the morning, I made coffee. We sat on the couch a bit, chatting with my roommate about her night before we finally showered and made our way to brunch at Trinity along the waterfront. We sat outside, yet again enjoying the nice Indian Summer we were having. When we finished eating, I walked him to the PATH to head home. Standing in front of the PATH, I kissed him. I’d never kissed a man in broad daylight in Hoboken before — Especially not in one of the busiest intersections in all of Hoboken in front of everyone watching Sunday football at the bar across the street. I was expanding my comfort zone, and certainly for a worthwhile cause.
As I left him, I had an abundance of energy. The endorphins were flowing! I kicked myself for ever doubting his feelings towards me and put his birthday party out of my mind. With that, I all but floated home. Hopefully, things would only go up from here.
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I left OCMD at 8:00am. My sister drove me back to Hoboken, and we made great time. I also managed to ramble off a few blog entries on the drive. So much for getting caught up while on vacation, but at least I was somewhat productive. I spent so much time hooking up and working on my tan, there was little left for anything else.
When I arrived home, I unpacked, but not before turning Grindr back on. There were more than a few guys I was courting before I left for vacation, and I wanted to touch base with them. I either texted them or waited until they were in Grindr range.
One guy I wasn’t expecting to touch base with again was a local police officer. Originally when I started talking to him, it took a lot to get that information out of him. He and I sparred verbally on Grindr a few weeks earlier. He had a day off and had tossed around the idea of meeting up. When push came to shove, he wouldn’t meet up.
This time, he was a black box with no picture and he messaged me out of the blue, “Hey. It’s [X] the cop. Wanna meet up today?” Apparently, he was in the area and had some free time between errands. All I had to do was unpack and grab a few groceries, so I obliged. He wasn’t giving me any ideas as far as what we were going to do. I told him he could come over and hang at my apartment, but I was a little worried he would take that to mean hookup. I also suggested taking a walk. Finally, I suggested we grab a coffee and maybe take a walk along the waterfront. Within ten minutes, he was at my apartment. I hopped in his car and shook his hand. He was a cut little hispanic boy who wore his hat on the very top of his head. He even had the cute gay slight hispanic lisp. I found it endearing. We chatted a bit in the car until we found a parking space near Starbucks.

When we ordered our coffee, he tried to insist on paying for me, but I wouldn’t let him. There was no need for him to pay. I’m stubborn that way when it comes to money and people paying for me.
After we got our coffees, we took a stroll along the water. We talked about his precinct and what it means to be an officer of the law. He told me about his partner and their dynamic. He seemed like a really nice down-to-earth guy, but I didn’t feel a spark there. I enjoyed his company, but could not see a relationship between the two of us.
The conversation turned to family and then evolved into his ex-boyfriend. He explained how it ended and how devastated he was when it did. My heart broke for him a little. I don’t know why, but I’m a sucker for heartbroken guys — Big soft spot for them. When our walk was over, we hopped back in the car and he drove me home. He had errands to get to, and I needed to get myself ready for my date that evening and to go back to work the next day after a week away.
Based on our interaction, I didn’t think he was all that into me, but I sent the text message, “It was nice meeting you.” He responded, “It was nice meeting you too.” In my mind, that was the end.
Almost a month later he texted me, but it was completely in the context of a hookup. When I called him on this, he tried to spin it as friends with benefits. It was 11:00 on a Monday night, and he wanted me to travel to his place. He wanted sex, and nothing more. That’s fine. I’m not judging, but I also wasn’t into the hookups so much anymore. The conversation was very blunt and polite. But, if we hung out again, it would simply be as friends, or possibly from a phone call for him to come get me out of trouble…
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