Posts Tagged first date

Never-Ending Date

I’d begun an amazing date with a spectacular man, and I couldn’t wait for what was to come next. Although I had been to Frankies 570 multiple times before with multiple dates, this time was special. I had an amazing guy to share a meal with. Ironically, my meal from days prior was so good, I ordered the same the again.

Conversation over dinner we great. It flowed like water downhill. We were both very flirtatious and chatty. On many of my other dates, there were long awkward pauses, but not on this one. Everything was just so easy. When I excuse myself to go to the bathroom, he leaned in requesting a kiss first. It was incredibly sweet and adorable. I really liked this guy. He was everything I was looking for.

I was just taking extra care to make sure I didn’t get ahead of myself. I had a history of falling for guys who would hurt me or not be interested in pursuing anything further. While in the restroom, I looked in the mirror to keep myself centered. All I could do was smile at my reflection like a giddy schoolgirl.

When I returned to the table, the conversation picked back up where we left off. My hand was on his leg under the table. His body language was very positive.

Our meals came, and we shared them with each other. Both of us were very happy with our selections. When the meal ended, we agreed to order a dessert to share. We got the crème-brulee. I dug my spoon into it and fed him a spoonful. It felt incredibly romantic. He smiled as his mouth closed around the spoon. We finished dessert and began to chat about what to do next. He was dancing around what I can only assume were his true motives. He said, “We can go have more drinks.” I interjected, “I don’t want to drink anymore.” “We can drop our bags at my place and go out. We could grab Pinkberry…” he added. I cut him off at the pass saying, “You can stop dancing around it. We can go back to your place.” He immediately smiled and agreed that was the best idea.

I wasn’t thinking we were going back to his place for sex. I knew there would be making out and a lot of heavy petting, but I wasn’t planning to give it up that easily. We hopped in a cab back to his apartment. He asked if I wanted to go to the roof, and I told him I would default to him. We were on his home turf. He could run the show. I picked the bar and restaurant. It was his turn to drive. Before we got to his place, he warned me of the condition of it. He informed me he lived like a frat boy.

When we got to his place, we stopped in his apartment on our way to the roof. I didn’t think he was as bad as he let on. We began making out on the bed. This, of course, led to many other things. Slowly but surely, clothes started landing on the floor in scattered piles. Eventually, we fond ourselves naked and engaging in a myriad of sexual acts, but penetration would never occur.

He was a very passionate man. I have found it nearly impossible to find a man whose intellect, wit and sense of adventure outside the bedroom matched their passion in the bedroom. He was a diamond in the rough. I wasn’t going to let this one go without a fight.

I noticed he was very into music. It was like he needed a soundtrack. I liked it. Every minute I was learning something new about him, and it was all making me like him even more.

We never made it to the roof. We ended up passing out on top of each other’s naked body. In the middle of the night, we both woke up. It was around 2:00. He offered for me to stay. I was under the impression that was already happening. I assumed I would just stay the night. We cuddled some more, and he turned out the lights.

When we woke in the morning, things weren’t awkward at all. I felt very comfortable with him. We talked about how we didn’t have sex and how that made us both happy. We didn’t need to rush things. I mean, I was spending the night on a first date, but I was happy true sex didn’t occur. I was also thrilled he was the type of guy who would just bring that up and not keep it inside for fear of saying the wrong thing. He spoke his mind. I needed to get back to that. Being with him might help me get back to that.

He was amazing. There was no question about it. We were both starving and decided to get dressed to hunt for some breakfast. We stopped by a few places before finally settling on Jimmy’s American Grill and Bar. We grabbed a table outside and picked up the conversation where we left off the previous night.

I let my freak flag fly. I felt so free with him. I told him all about me and my idiosyncrasies. I explained my Christmas Bash and all the work I put into it. He referred to me as Martha Stewart, and I expressed my hatred for that referral. I didn’t like that my cooking and entertaining had a feminine connotation. I told him I was more the Nate Berkus type. He laughed and agreed it was a better reference. I told him about my crazy coworkers and how we would make an amazing reality show. I told him about growing up on a farm. Everything I could think of, I brought out. He loved it all! I learned about where he grew up and his career in advertising. Every word made me like him more and more. He also told me about his friends. They texted him while we were eating to ask him to come to brunch 2.0.

Somehow, we got on the topic of The Hunger Games. I was reading the books, and he had already seen the movie. I told him I was looking forward to seeing the movie. He told me he would go see it again and asked if we could go see it Sunday. You could have knocked me over with a feather. He was already planning date number two before date number one concluded. I was thrilled and immediately accepted.

He walked me to the PATH to say goodbye before heading downtown to meet his friends at Elmo. We kissed each other goodbye and gave a long lasting hug. There was a homeless man panhandling next to us who said, “Get a room,” through a smile. He began laughing, and I started to crack up since I was the one facing him. I said to my amazing date, “That made my day.” Immediately, he replied, “You made my day.” I was in heaven. I said goodbye and went down the stairs to the train.

Later, I learned from checking his Twitter that when he checked in at dinner on Foursquare, he wrote, “Easy conversation + tasty food + hot boy = great date on a Fri night (@ Frankies 570 w/ 2 others)” and the next day at brunch, “When last night’s date becomes this afternoon’s brunch date (@ Jimmy’s American Grill & Bar). He really did like me. I was just finding it hard to take. It was like a dream. I couldn’t really believe it. I didn’t want to get too excited because I didn’t want to get hurt. But, honestly, who gives a f*ck. I was happy, and that was all I cared about.

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Another Boring Date

Tuesday night, I was happy to be home. My date with S.D. wasn’t bad, but it helped me realize he wasn’t the guy for me. We had too many differences of opinion.

I noticed on my calendar Broadway‘s birthday had arrived. I made sure to call him to wish him a happy birthday, but he didn’t answer. If I recalled correctly, he was in California for a vacation. I left him a message and told him to call me when he had a free second. I didn’t hear back from him for over a week. I was a little disappointed, however, we still maintain a friendship. His friendship is important to me.

On my walk to work Wednesday morning, I checked my Grindr messages. I began to chat with one guy, but that’s another story for another day…

I had a date planned that Wednesday with a guy I chatted with on OKCupid, but he ended up bailing on me at the last-minute. This time, I had no one waiting in the wings. I debated just lying low and going home after work, but another part of me didn’t want to waste a free night. I thought I’d reach out to my current roster to see if any of the guys were free to meet. I figured I might as well get a first date out of the way while I had the time. I was really looking at dating like a job. This was bad policy, but with someone like me who has a busy schedule, you gotta do what you gotta do. I sent out feelers to the guys to see who was available to grab a drink after work.

Ironically, two of the guys responded. One was in Hell’s Kitchen and the other lived in Jersey City. I wondered if I could schedule them both in the same night. Hell’s Kitchen would work out because I could just take the bus home, and Jersey City could work if he came to Hoboken to grab a coffee or a drink when I got home later. I wasn’t all that psyched about the guy from Hell’s Kitchen, so I assumed it would be a short date and work out.

The first guy picked a nice restaurant, Pier 9, at the north end of Hell’s Kitchen to grab a drink and maybe an appetizer. It just so happened to be right across the street from his apartment. We met just inside the restaurant. I wasn’t excited by what I saw. He wasn’t unattractive, but he wasn’t attractive either. That being said, I wasn’t writing him off based on looks.

He was a regular here. He knew a lot of the wait staff, and they took good care of him. We grabbed a seat and began to chat.

The conversation was pretty relaxed. We both decided to order wine, and since it was happy hour, we split a bottle at half price. We also noticed a great edamame appetizer on the table next to us and ordered that to split while we got to know each other. It was a very nice place, and the wait staff was super sweet to us. They could tell we were on a date and treated us as such.

We talked about our jobs, our families, life in the city, etc. It was nice conversation. Nothing was forced or awkward, but there was no spark either. He seemed like a really nice guy, and we agreed on a lot of things. I could see us getting along really well, but more in a friendship capacity than a dating one. I could see him being a good date for Sunday morning brunch to talk about the weekend and talk about guys.

We were there for a decent chunk of time. The date lasted about an hour all said and done. We finished the bottle and the appetizer and decided it was time to head out. I could tell he didn’t find a strong connection there either. I had to initiate the goodbye hug, and there certainly was no feeling behind it. This would make things easier. We left with the same expectations of not hearing from the other much after we parted ways.

As I walked to the bus, I started texting the guy from Jersey City. We’d talked more than a few times before. We’d become Facebook friends, and I was supposed to see him on Hoboken St. Patty’s when he was attending the gay party across the street from my apartment, but he never made it. I asked him to an unconventional date. I lined it up for him to come to my place and just relax with a glass of wine. He agreed that sounded like a great idea, so he came over shortly after I came home. We were finally making time to meet up in person…

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Two Hours

After coming to the realization Middle Eastern was not dating material, I began my search for a boyfriend once again. I thought I’d give him a second chance, and he proved to me he wasn’t worthy of that.

I went back to my matchmaker once again – Grindr. I was a little addicted. I found myself spending hours out of my day on the app. I was searching with great fervor. When I woke in the morning, the first thing I did was reach for my phone and fire up Grindr. The next thing I did was grab my tablet and fire up Grindr on that. It was even better on my tablet. The pictures were bigger, I could multitask with my phone, etc. I fully realized how much time I was spending searching for a man. I saw how much of my day was stolen from me. It was like a second job.

On a few occasions, I would strike up a conversation with a guy I thought worthy of my time. One such man lived nearby in Jersey City. We started chatting on Grindr, and I did what I always do. I asked him for his number so I could take things out of the Grindr app and start a conversation over text. I always asked for a picture from the start so I could keep the guys straight in my phone contact list. I kid you not when I tell you I have around 100 contacts from Grindr, Adam4adam.com, ManHunt and OKCupid. I had a system in place as well. Everyone’s name began with where I met them. I was cataloging these guys in theory. Some I never spoke to on the phone, let alone met them in person, but they were saved no less.

After getting this guy’s number, We texted about chatting on the phone some night. He picked up the phone and called me. This earned him a lot of brownie points in my book.

We started with the superficial things – Where we lived. He told me all about his building. I was quite familiar with it. I’d run past it on many occasions. This morphed into a discussion about where we grew up. He was fascinated to learn I grew up out in the country on a farm. Through texting, I’d already learned he was from Canada. I told him how surprised I was he didn’t have a Canadian accent. It popped up a few times, but quite infrequently for someone who grew up there.

I quickly learned he certainly fit the Canadian nice guy stereotype. Everything he said was sweet and polite.

I learned he was slightly older than me. This wasn’t an issue for either of us. I had always liked slightly older men, but I am always leery that older men aren’t thrilled with dating a younger man. I’m quite mature for my age, so I hope my personality can make up for the age gap.

We chatted about our jobs, and I learned he worked in the travel industry. He jetted around the country and internationally quite frequently. He even mentioned the possibility of taking someone like me with him on said trips. I wasn’t getting ahead of myself, but I did enjoy the idea of traveling with my boyfriend to far off locations. He detailed many of the perks, which I really enjoyed, but I didn’t want to let that cloud my perception of him. On the flip side, I told him one of my most embarrassing secrets. I told him I’d never left the country with the exception of Windsor Canada from Detroit. He told me it wasn’t a big deal, and he would help me remedy that issue.

Somehow we got on to the topic of dating and being single and previous lovers. He wasn’t very forthcoming with the information of his major heartbreak, but all it took was one question for him to tell me the overarching story. It seemed it was a sensitive subject, but he was willing to tell me the story. He was dating a man for seven years. This was before he was traveling for work. He was scheduled to go away for work, and at the last-minute, his trip was cancelled. He came home to their shared residence to find his boyfriend in their bed with another man. I expressed my grave sympathy. After seven years with someone he must have been crushed. My heart broke for him. He told me he simply told his boyfriend he needed to move out and that was the end of them.

I tried to lighten the mood and asked him what he likes to drink. Ironically, our lists shared a lot of the same drinks. It was uncanny how similar our pallets are. I learned he too is a fan of Malbec. We discussed how it would need to be present on our first date. I was happy we were on the topic of meeting for a date. He seemed like a great guy. Maybe he was the ship I was searching for in the storm.

I asked him what he was looking for, and he described his ideal situation. Amazingly, our perfect pictures lined up quite impressively. I was really excited to meet him. I only had one picture, and he appeared to be an attractive man. I was more excited to meet him to see how strong the chemistry would be. It was already pretty strong considering we spoke on the phone for two hours.

Only time would tell, and we made tentative plans to grab a drink or dinner in the near future.

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Connecticut Cutie

Since I’ve been slacking, I’m going to make it up to you this week. Hope you don’t have a busy week, because you’ve got a lot of content coming your way!

For as long as I can remember, I was trying to nail down a date with a specific guy I met on adam4adam.com. He had the cutest smile that could light up a room (in case you haven’t noticed — and I’m just coming to this realization — I’m a sucker for smiles). He messaged a few times on a4a, but nothing ever materialized.

Months passed, but I could never seem to get him to meet me. He’d show a lot of interest, and then he’d disappear for a bit. Like the ocean, it was a constant ebb and flow with him. Finally, I just flat out gave up on him, and I didn’t hear from him again. When I broke up with Smiles, I went back through my saved messages and decided to hit him up and see if this time would be different.

Ironically enough, I learned he moved out of the city. He was originally from Connecticut, and he moved back home with his parents to save a little money. It seemed now he was interested in finally meeting me, just when it would be most difficult. We discussed many evenings as possibilities to grab a drink before we finally found a good day to grab lunch. Even then, we were playing things by ear.

Of course, this didn’t happen. He had to cancel on me. However, he proposed raincheck options. He agreed to meet me for a drink one night after work on his way to Grand Central to hop on Metro North to CT. I did some research to find a bar that would be convenient for both of us. We set a time, and I told him to meet me at Annie Moran’s by Grand Central Station.

I was already having reservations about this guy. Was this how it was going to be all the time. Quick rendezvous before he went home? I finished work before him, so I decided to walk there instead of taking a subway or cab. It was raining lightly, so I broke out my umbrella, however I wasn’t walking alone. I had Grindr to keep me company while I walked. I’m such a whore. I was already looking for the next date before this one even got off the ground. But, it’s what you gotta do if you have an aversion to gay clubs. I stood outside the bar paging through profiles while I waited for him to arrive. He too was walking from work, and he worked about fifteen blocks away.

Just before he walked up, he gave me a call. I told him where I was, and when he saw me he hung up. As he walked towards me, he wasn’t quite what I was expecting. It wasn’t a bad thing; he was just smaller than I originally thought. We greeted each other with a handshake, and with that made our way into the bar. He offered to buy me a drink since I’d been waiting for him. I was in charge of watching our bags and trying to find a piece of real estate to stand/sit and chat.

He came back with the beers, and we dove into conversation. It was slow going at first, going through the standard order of questions. As he talked about his job in fashion, I noticed a bit of flamboyance coming through. I wasn’t thrilled, but it was far from a deal breaker. He was certainly cute (although he looked much cuter in his pictures before he cut his hair shorter).

We talked about family, work, his moving back home, where I live and grew up, commuting nightmares, etc. It was nice. I couldn’t quite tell if he was all that into me. I was starting to think he thought I was too “straight” for him. But, as the conversation progressed, his body language began to change. I realized he may have just been nervous. Once he relaxed, I could tell, he was flirting a little heavier. After the first beer, he asked if I wanted another. I gladly accepted. I figured he was going to dictate the end of the date since he was the one who had to catch a train. He told me all about his curfew and how he’d have to take a taxi if it got past a certain hour; his parents would no longer pick him up.

We talked about watching sports on TV and participating in them. Somehow skiing came up, and I told him my story about the first time I skied and how well I did. When the group next to us lef their table I snatched it, while he got us a third round of drinks. The date was going well, or at least I thought so.

While we sat, he took the opportunity to touch my leg periodically. I love that. It’s a surefire sign of interest. I returned the favor as well. I could tell there was a lot of sexual energy between us as well. We were both feeling it. We talked more about what we do for fun when we’er not working. He told me about his old apartment and how he still comes back into the city to do rotating dinner with friends at their respectful apartments. There were slight awkward pauses, but that can be warranted on a first date.

When he finished his third beer, he told me he had to be running for his train. I thanked him for picking up the tab, and I told him I would pay next time. “If there can be a next time,” I added. I walked him to the doors of Grand Central and said goodbye. He was lingering, and I could tell he wanted a kiss. I wasn’t sure his position on PDA, but I decided to go for it. I wanted a kiss, so I was going to get one. I leaned in with my arm behind his back and gave him a nice quick kiss goodbye. We agreed to find time to see each other again soon as we parted ways.

On my ride home, I took the opportunity to text him and let him know I thought he was cute. He told he had a great time, but also told me how he’d locked himself in the bathroom on the train. It was a really funny story, and I was happy to hear he had such a great sense of humor and easy-going personality. He told me he wanted to grab lunch later in the week, and I agreed. We would figure out a time that worked for us both. I was already looking forward to it…

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