Posts Tagged older gentleman


I’ve been on Grindr for quite some time now. I’ve come to remember certain things about certain guys on there. I recognize when new guys come up, and I recognize when guys I’ve spoken to in the past pop up as well.

N and I have always had an awkward relationship when it came to Grindr. It was how we met, but it was also the catalyst for him cheating on me (and me cheating on him).

After I broke up with Smiles, he asked me to keep a lookout for a guy impersonating him on there. I was so thrilled he found an opportunity to capitalize on my failing relationship in some way. It was so typical of him. He’d also mentioned that a friend found me on there shortly after breaking up with Smiles. The story he gave me sounded like such b.s. I could see right through it. I could tell he had a secret profile himself because what he proposed happened would never have happened. He had a serious boyfriend, and I seriously suspected he was still using the app, just on the dl this time.

One day, I thought I discovered his secret profile. The language he used in the description was spot on for things he’s said on his profile in the past. There also was no picture attached, so his boyfriend wouldn’t be able to find him if he tried. I messaged the profile saying: “Is this [Neighbor’s] secret profile?”

It took a long time, maybe a day perhaps, but the profile responded to me. He asked if he knew me, but I played dumb. I proposed my idea of who he was, but he wasn’t answering me straight. Finally, he said he wasn’t who I thought he was.

We started to chat about different things. He asked where I lived. I told him where I live and where I’d recently moved from. He commented about how I’ve lived in the back end of Hoboken for the most part. I told him I care more about what was inside my apartment than where I lived location wise.

He asked what gym I go to, and I told him. I told him my reservations about NYSC based on the stories N told me, as well as many of even my straight friends. He told me how he felt the same way, and because of this, he goes to Club H.

When I was detailing the sketchiness I knew about NYSC, he became more curious. He asked what my ex told me went down there. I told him he told me guys rub and tug in the steam room. I told him my ex told me about participating once before he met me. An older gentleman walked over to him and lifted off his towel, exposing him. He then proceeded to blow him. I was shocked by this because anyone could walk in at any time. He told me he was never able to stretch in there because guys were constantly dropping their towels at him and propositioning him.

He then started asking a lot of questions about my ex. He asked why we broke up. I told him about catching him flirting with other guys on Grindr and sending naked pictures of himself to other guys “he was just messaging to be friends with.” He asked if I had a picture of him, so I looked through my phone and sent it. I felt a little guilty, but then again I didn’t. N certainly didn’t show me the respect I deserved, so why should I give him respect in return. Besides, I wasn’t really doing anything wrong. I was only telling the truth, and the picture I sent was fully clothed. At this point, I still wasn’t sure he wasn’t N pretending to be someone else to pump me for information, but like I said, I wasn’t saying anything untrue. I was being honest and civilized about it.

“No offense, but he’s not very good looking,” he added. I smiled from ear to ear. “Like my apartments, I choose my men based more on what’s on the inside,” I told him. I chuckled in my mind and out-loud because N always thought he was an adonis. He was decently attractive, but not enough to warrant his ego. He went on to insult his looks further. At this point, I had a feeling it wasn’t N or one of his friends.

Then he asked if he was good in bed. I told him I didn’t want to talk about my ex anymore and tried to change the subject. “That means no, haha,” he joked. I said, “Not necessarily. He was new when he met me. I broke him in and showed him the ropes. I put in all the legwork for his current boyfriend.” “How do you feel about that? Does that make you mad?” he asked. I told him I didn’t care anymore. It wasn’t my concern, and we weren’t exactly friends anymore. I told him how I’d put in the effort to continue to be his friend, but I couldn’t be bothered anymore. When he asked why we’re barely friends, I told him about how N never put in any effort toward friendship unless there was something in it for him. “He’s too conceited, that’s why,” I added.

At this point, I was a little suspect this guy was the one who was impersonating N on Grindr. It seemed he knew something or was pumping me for information, because every time I would try to change the subject, he would circle back. Once again, I just answered all the questions I was asked honestly. I asked him to send me pictures, which he did. I’d never seen him before. I started to ask him what brought him to Grindr, and I immediately was blocked by him. It was a very unusual turn of events. I was highly annoyed, but there was nothing I could do about it. I shrugged it off, and went on with my day.

I knew this wasn’t the end of it. I knew there would be some hell to pay, but I was ready for it. That, and I DIDN’T CARE! Screw him. He wasn’t adding any value to my life. He was one of the exs I no longer needed to concern myself with.

Of course, while traveling for business the next day, I received a text from N: “Hey bud… So this is going to be random. But you never spoke to anyone about me on Grindr recently have you?” Yup. I was right. It was someone pumping me for information so they could run back to him with it in some fashion.

I decided this wasn’t worth my time. I didn’t respond. I just laughed out loud to myself and put my phone away. It was my turn to talk to other guys on Grindr.

I told all my friends about what happened, and they loved it. They have not been a fan of his since they learned all the sh*t he was pulling behind my back. He was useless dead weight in my life, and it was time to cut him free. I no longer needed that baggage. He proved he didn’t care enough to keep me a part of his life. I was going to spend more time concentrating on my good friends and new lovers. I was done living in the past.

That night, I texted the southern guy to see when we were actually going to get together. We’d had two great hour long phone conversations. I was looking forward to meeting him in person. I asked what he was up to the following night, and he responded back, “Yeah… I have a date, LOL.” I was p*ssed. He had a lot of nerve. He knew I was interested. I made that clear. It was incredibly rude to respond in that way. What was laugh out loud worthy of that!? I didn’t want to give him the benefit of an angry response, so I just said, “Enjoy. I take it you’ve lost interest then?”

“No, I just met someone last week at work (since I barely have a life outside of it) and we’ve had a few dates. Seeing where it’s going. We haven’t even kissed yet,” he detailed. “Not gonna lie. I’m pretty disappointed. Been trying to meet up with you for weeks. Nothing I can do about it though,” I told him. I was hurt, but I wanted to be honest. He tried consoling me by saying: “I’m sorry. It just happened. It doesn’t mean we can’t grab a drink. I just want to be completely up front. The opposite of the guys up here who are dating and f*cking 7 people at a time.” I wasn’t going to play this game. “Well my friend, the ball is in your court. You know how to reach me if you’re ever up for that drink…” I was done chasing men who showed no interest in dating me. I had better things to do with my time.

I also made a new rule. I was no longer going to try to date flakes who worked at Ralph Lauren. This was the fourth guy who worked there who burned me. I know this sounds petty, but I wasn’t about to let it happen again…

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Deep Pockets

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 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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