Chronicles of an Online Dater


So I have joined free dating websites in the past but never took it seriously. On June 1st, I joined just to see the options out there in the cyber world. It's been an interesting experience to say the least.


The first guy I met was a nice guy, Mike. He's 36, runs the family company, Christian. All good things. I discovered we even attended the same church and soon discovered that we had mutual friends. One came into the conversation. An old friend that disappeared when he started dating his now wife. I'm not sure if I sounded a little heartbroken by the incident but that was the last I heard of Mike.


A few days later I met Giovanni. He was also nice and Christian. 30 and Peruvian. He was a building supervisor. I like a handy guy. He left me a voice mail one day and I just didn't like his voice and then had second thoughts about being physically attracted to him. So I texted him that I would like to be friends and since that day, I never heard back from him.


Next was Troy. Our first conversation was on chat and we quickly learned that we thought the same way. Which was a plus. Troy's 34. An accountant. Half Cuban, half Irish. We exchanged numbers and texted often for a week before our date on a Friday night. Upon first meeting him, I regreted instantly that we had never spoke on the phone. His voice sounds a little effeminate if you catch my drift. We walked around an outdoor mall and then sat for a while. He sat too close for a first date in my opinion and it made me a little uncomfortable. Then we went to a pool hall and played a game if you can call it that. We were both dreadful at billiards. He was just as uncoordinated as I was. It was a turn-off. After we went back outside and talked some more. He was easy to talk to but the coversation was extremely boring. A lot about work and family. I enjoyed the ease of our conversation but it was a yawnfest. I made the mistake of mentioning that we could do something else at the end of the night and I quickly realized my mistake. He texted me that he had a good time and the next morning I responded that I just wanted to be friends. He responded "sounds good". I had the feeling that would be the end of that. Guys do not take kindly to being friend-zoned. But shockingly a few days later I started to hear from him again and in the last month we developed a real friendship. We've had conversations about politics and religion and we are both on the same page which is so rare. But I couldn't change my thoughts about him so easily. I won't write him off completely but at least for now. 


That week I started talking to Frantz. African American with braids. 29. Six-pack. Part time actor, part time gym teacher. Christian. A departure from the guys I've met until this point in my online search and in real life. We hit it off. We liked the same bands and he was funny. But my parents wouldn't be thrilled with me dating a black guy. I have nothing against it but they do and I rather not cause drama at home so I told him I was interested in someone else and that if we could be friends. Never heard from him again.


Later that week I winked at a guy named James. He messaged me his number. Didn't even try to have a conversation on the website first. Before even adding the number to my contacts I decided to google the number. The first search showed that he worked for an aviation company that gave tours around the area. Nice. There I found out his full name which I googled as well. First search result was a mugshot and a news article from 2008. The article stated that he graduated from Harvard and was practicing law when he was involved in lawsuits against him and malpractice. He represented himself in the proceedings and it sounded like he was acquitted. But what a shock. Save to say I did not call him.


A couple days later a guy started a chat with me. He was cute. Don't remember if he told me his name. He was American but he complimented me in Spanish which was flattering to say the least. Then he said he had to be upfront about something. I thought he was going to say he had a kid or he was a virgin or something like that. Come to find out that the big secret was that he was a nudist and he enjoyed going to nude beaches. I did not expect that at all. That was the end of that conversation. Wow.


During this time with the last three guys I was messaging with a guy named Ben. He was 26 and a teacher. He looked young and while I wasn't against dating younger guys I worried that the maturity level would cause problems. In our conversations he seemed a bit pretentious and I felt like I couldn't be myself with him. We had similar taste in movies and music and he was sort of cute so I agreed to go on a date with him. I didn't have high expectations but had an open mind. I made the same mistake and didn't talk to this guy on the phone before either. When I was on my way to our date, he texted me that he would be 15-20 minutes late. I was already driving to the location so I decided to just wait for him there. We were meeting for smoothies. Good, no pressure, low key date. It turned out to not be in the best area of town but I was there so there was no turning back now. After waiting for 30 minutes, he showed a T-shirt. He was a nerd, a huge nerd. His voice was nerdy. His demeanor. Everything. It was hard not to end it right there but I felt bad and the date continued. Thankfully I had plans in an hour and a half so it wouldn't be dragged out like the last date. I quickly realized that this guy was going to take over the conversation. He asked maybe two questions the entire date and nearly every time I tried to talk he interrupted me. We had things in common but his social awkwardness and rudeness was pretty much a deal breaker. He asked if we could go out again and I felt bad so I said "maybe". Then he asked if he could call me and I answered with bregrudgedly, "Sure". Thankfully I would not have to reject him because he never contacted me again. 


A week later a guy named Maury messaged me. He was witty. His profile came off a little arrogant but charming at the same time. He listed his faith as "spiritual but not religious". This should have been the end of that but this guy was the hottest guy yet and I'll admit I was a little overeager. I carried the conversation asking him most of the questions and when each topic fizzled, I brought up a new topic. I was even the one that suggested we exchange phone numbers. Late that night we talked on the phone for over an hour. We had a great conversation. I loved the sound of his voice and we laughed a bit. Even though I was nervous, he kept the conversation going and tried to make me comfortable. We agreed to meet at a British pub a few days later. Over the next few days leading up to the date, he didn't really text me or anything. So I brought it upon myself to text him. Big mistake being so forward. But finally date night came around. He met me about 10 minutes after the agreed time. That's fine. He kissed me on the cheek when we met and I noticed that he was the same height as me with heels on. Not a deal breaker. We sat at the bar at first which I did not like. I felt uncomfortable especially since we had to turn our heads to talk to each other. We ended up in a cozy English tea time table. It was hard to talk here too because we had to lean far into the table to hear each other over the music. It wasn't a big deal because we laughed about the circumstances. If I had to say the most common thing out of his mouth, it was "I don't care". It seemed every topic we discussed that he was indifferent towards. And I don't know why this wasn't a red flag in my mind. We talked for three hours and in that time he had four beers which should have been another warning sign. I think I was distracted by his good looks. His piercing eyes and his dimples. At the end of the night we were already planning the next date. But over the next few days I thought this match through and felt it was all wrong. But I still wanted to see him again. I tried to rush our second date into happening sooner which may have come off as being stalkerish. So at some point he stopped responding to my texts and then the last nail in the coffin, deleting me on Facebook. So that was the end of that.


Or was it? A week later, my pathetic self decided it was a good idea to send this guy a message. I thought he had blocked me on the dating website so that he wouldn't see the message. But sure enough, moments later he responded. He said I had come on too strong, etc. I completely agreed. Then he said that he didn't wish to be friends but "something more". I latched onto those words and texted him about that I was only physically attracted to him. And the conversation took a dangerous turn. I had a doctor's appointment that day but when I got home I impulsively asked if he wanted to meet at the movie theater. And of course the intention was to make out and then some. It felt like a real date. He had his arm around me or on my knee the entire time. After close to three years of not having any intimacy with a guy, I have to admit it felt amazing.


Later that night, he suddenly decided to be completely honest with me and said that he liked me but that he was in love with someone else. We had a heart-to-heart conversation, and we connected on a deeper level than I thought we ever would. It felt like our status had changed and the attraction went from physical to emotional but was still not enough to warrant a relationship. We agreed to be friends even though we continuted talking about our attraction for each other. Then I continued my old ways. I texted him incessantly and nearly drove him away a second time. I wanted to hang out with him as friends because I knew deep down he was a good person whose company I would enjoy. At the last minute he cancelled on me and I realized the error of my ways. We could never be true friends. Not with the lust between us. 


While all of this was going on, I had been messaging with three other guys. The first, Juan, was one of the nicer guys I had spoken too but I wasn't attracted to him at all. He was heavy set and his personality fell flat. The next guy Tommy was very attractive but he didn't seem too interested. He took my phone number but only texted me a few times. Lastly, there was Anthony. He had to be the sweetest guy I met in this entire experience. He had messaged me towards the beginning of my membership and I ignored him. Then he persisted. He was very nice and asked a lot of questions about my profile, interests, etc. And he also liked to talk way too much. It turned me off having to read these long-winded essays. Also the fact that he was a devout Catholic and not a Christian was a concern. So I let him down easy and never gave him my phone number.


The next guy I talked to was named Aaron. He favorited me and we messaged only a little one week and then a week later he messaged me again and we got to know each other. He lived an hour away in a very small town and was a farmer. I always liked the cowboy look but this was pushing it. But we found that we had many things in common. He was funny and sweet and soon I was getting excited about going out with him. Then one day I asked if he had a Facebook and he said he had deleted it but he gave me his full name and I googled him. First I saw several websites about his business which was legitimate. Then I found his MySpace. I knew from his dating profile that he was a little heavier set which was fine but he was much bigger in the pictures on MySpace. I asked him about it, and he noticeably grew paranoid that I wasn't attracted to him anymore. I also sarcastically mentioned that there were only girls in his pictures and he said "Guys don't take pictures together." But I didn't see any other guys in the group shots. Then since he had an unusual name I was able to find his Facebook. It was active and had activity in the last month. So it seemed suspicious that he would hide that. I started to get a bad feeling about him coupled with that in looking at more of his pictures I wasn't as attracted to him as before. I don't want to be shallow but he just looked old. If we dated he would look 15 years older than me. I decided to sleep on it and see how I felt in the morning. I called off our date and he responded "Peace out." which I found kind of rude. Later that day I noticed that he deleted his dating profile so then I felt horribly guilty thinking it was because of me.


The search continues. I haven't given up hope but I am trying to be more selective. 


Next up was Brian. He was the first result when I searched on the website. My first impression was his headline which was a lyric to the song I had said I wanted to be my first dance at my wedding. He's bald and a little chubby and Cuban. He likes so many of the same things I did including hockey and music. He played guitar and was left-handed like my father. I've always loved musicians. I winked at him and emailed him. When I didn't hear back I found and added him on Instagram just in case he was not a paying member and could not see my e-mail. Hours later he finally responded to my e-mail. We described ourselves then he suggested we get together sometime. This all happened on a Friday. I found out his full name so I looked him on Facebook. I discovered we had two mutual friends. One that I knew from middle school and an older woman who I had know since I was very young and I had just reconnected with. I reached out to her to get information on Brian. She told me to call her so I grew concerned. I browsed through his Facebook and found pictures with this woman's daughter and I quickly gathered that they used to date. So I finally talked to the ex-mother-in-law and she informed me that she didn't think he was really a Christian, that he was immature, and that he had no ambition. These were all concerns and inklings I had from looking through his profile and social media. He reminded me of my father in the sense that he didn't have the drive to provide for himself and his future family. I did not want to marry my dad. At all. This was one of things that I know rocked my parent's marriage on a regular basis. I did not want to earn more money than my husband because I know it causes a rift in the relationship. So I talked to him on Friday and didn't hear from him all weekend; he said he had a death in the family so I assumed he was grieving. On Monday I sent a message that I hoped he had a good weekend. No response. On Thursday, he finally apologized for not contacting me and that he was having "a rough week".


While the Brian situation was going on, another guy named Chris sent me a message. We didn't have too much in common so I was going to ignore it but decided to respond. He liked football and was a country boy from Texas. Unlike Brian, he had a great job, probably the best of all the guys I had spoken to until that point. He ended up being funny and very nice. We also had a lot of the same viewpoints. We messaged each other for a little less than a week before I broke down and asked him for his phone number because I was getting annoyed with the dating app. I basically asked him out too. It wasn't that I was overeager but I knew he wasn't going to ask for fear that it would make me uncomfortable. We set the date for a Sunday to meet for lunch and maybe a few games at the arcade. He was the first guy to get to our date early which was a great start. I immediately noticed his Texan accent which I liked very much. The conversation over lunch flowed naturally. I felt very comfortable with him. When he was talking I couldn't help staring at him. He was very good looking, more so in person than in the pictures I had seen previously. After the date we walked around the mall. He said he was a great shopping partner so I took him to a couple stores where I wanted to look for something. He helped me by picking out options which I 've rarely if ever experienced. Afterwards we went to the arcade. We played air hockey, basketball, skee ball, and other games. I was beating him most of the time and it was a good way to flirt with him a little. He enjoyed my sarcasm (I think). We ended the date and he gave me a side hug which I appreciated that he was moving slow. After the date, he texted me maybe the sweetest message I have ever received- that he enjoyed my company and that I was more gorgeous than he could have imagined. 


For the second date, he asked me to meet his at his office and I wanted to do some shopping so he helped me pick out a pair of sunglasses. Then we walked around the shopping center. We finally went to eat at a BBQ restaurant there. We shared chicken wings which he ate with a knife and fork and I ate with my hands, getting sauce all over my fingers and licking it off. He kept staring at me doing this and smiling. After dinner we walked nearby to get some frozen yogurt, sat on a bench for two hours and just talked. It was a great conversation. Finally we had to call it a night because I had to go to sleep early for work. When we went back to his office to pick up my car he gave me a tour of his office then gave me a couple pecks and a hug before he left. We agreed to get together again in a few days but the following morning, I realized I wanted to see him again that same night. That night he picked me up at my house and we went to a park a few blocks away. There was a thunderstorm close by so the Aussie park ranger told us to seek shelter so we spent the majority of the time sitting on a swing and a park bench. I kept being sarcastic with him and he would pretend to take it personally then say I was adorable. We had to leave at sundown so we drove around and did some more shopping then I got hungry so we got some drive thru KFC. He drove me home and we sat in his car making out. He is a very good kisser. Thankfully. Very passionate and he kept looking at me adoringly in between kisses. I asked him if he wanted to go inside my house since my parents were upstairs and we sat on the couch and cuddled some more and kissed a lot. I didn't want it to be over; it was a perfect night. 


We planned our fourth date on a Saturday. We were going to go on an airboat. That morning he texted me that he was throwing up all morning. I was devastated. I was so looking forward to this date since the last one was so great. Then I started thinking maybe he was lying. I don't know why. I was so sad that I wouldn't see him over the weekend that I decided to buy some groceries, items that you want when you are sick, and look for his house and deliver them. On Sunday, I went shopping and he had hinted before where he lived and that I could look for his truck to find his apartment. I was hoping that by the time I would get to his complex he would have woken up but he hadn't. I found his truck and called him. He graciously accepted the gift. I was mostly curious to see his apartment. He gave me a quick tour and I was on my way. He was going out of town on Wednesday through Sunday so I really wanted to see him before he left. He met me for fifteen minutes in the parking lot of a nearby mall. I cried because he felt distant and I thought I was losing him.


The Monday after his trip he was supposed to come over my house. He had some errands to run so I waited by the phone. He was giving me the play by play then suddenly I didn't hear from him for over an hour. I got paranoid again. Finally he texted me that he had fallen asleep and apologized profusely. We agreed to meet on Wednesday. By this point it had been a week since we saw each other and two weeks since a real date. I was so annoyed with how things were going. On Wednesday we planned to go to dinner but of course he had a last minute meeting and had to postpone. He told me to go over to his apartment at around 8 PM. I didn't really want to go anywhere and it was getting too late anyway. So we just sat at his dining table and talked. Then I told him I wanted to go and sit on the couch. One thing led to another. He was so passionate. Throwing me on the carpet and carrying me over to the recliner. Then he commented that I was against going to the bed and I said it was fine so we made out some more in his bed. It was another great night even though I didn't want to move this fast. The next time I saw him was a Monday, Labor Day. We were going to drive to Jungle Island. When I met him at his apartment it looked like it was going to rain but he obliged and drove down to Miami Beach. The drive was awkward. He was kind of mean and I wasn't taking it well. When we arrived it was pouring down rain so when it didn't let up, we left. He got a call on the way north that he needed to take care of a work situation so he went to do that and he said I could come over after. Instead he worked the rest of the night.


The next time was Thursday. I wanted to go to this concert and food truck event. Right before we were supposed to meet he remembered that it was the first football game of the season and said I could still go over to his apartment if I wanted to. I did and we watched football. When he didn't touch me after a couple hours I got paranoid again and inquired why. He said that I should make the move sometimes so I did. The whole rest of the game I wouldn't stop talking or kissing him or cuddling with him. He didn't seem that enthusiastic. He acted like he was mad but would still smile at me. When I left he said he had met the perfect woman. I said I didn't believe him. On Saturday I had morning plans but had hoped to see him at night. He misunderstood that I had all day plans and went to a car show instead.


On Sunday morning we agreed to watch a movie. It started at noon but he hinted that he might not be awake. I said I would wake him up at 11. I was so mad that day because he wasn't making an effort and I did as I said I would. I showed up at his apartment at 11:15. I felt like this would be the last straw and the end. He groggily opened the door and went back to bed. I lied next to him in a quiet rage. He reasoned that he liked to sleep in on the weekend because he worked hard all week. I felt it was an attack on me. He said I had to sacrifice for him but he never sacrificed for me. I said I would start crying and I did. I don't remember what I said but I said some mean things basically expecting him to end it. He didn't. He said I needed to slow down but that he wasn't going anywhere. Then he said he was going to go to work. He hugged me and gave me a peck. I felt slightly better about the situation but not at peace. That would be the last time I would see him. The following week we texted all day long but he never tried to set another date. When the entire weekend had passed and still nothing, I was mad. On Monday, I asked him why. He said it was how he was; he worked and relaxed. He said it had nothing to do with me. Then I continued to pry and he said he was walking away because I was pressuring him. It was over after a month and a half. I was sad but happy at the same time that it ended quickly. I couldn't take this charade anymore. It was ridiculous. He was ridiculous. I know I said some crazy things but he won the prize. Did he expect me to wait around forever? So many failed dates should have been a sign that it wasn't going to work out.


And so concludes my experiences with online dating. I learned quite a bit in the adventure. I learned what I like and what I don't like. I learned that I still have many issues to overcome before I can be in a healthy relationship. I see I can still be needy and crave attention to the point of doing stupid things to receive it. 

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KindredSpirit's picture


I have never.

What a  long strange trip it is.

It is good to have someone

That you can depend on.