A Recollection of Online Dating (mis)Adventures

I've spent the past several weeks reading the open journals of a few members on this forum, and I've decided to give it a go myself. I found that reading the posts was oddly therapeutic. I've always wanted to keep a journal, but know I wouldn't keep up with writing my experiences on paper. This seems like a great place to start, and I welcome any feedback or comments

I want to start by chronicling my experiences with dating over the past few years since I moved back to my hometown after college. I've been on A LOT of dates (99% of which were from online dating) but haven't met "the one" as of yet. I am hoping that by putting my encounters on "paper" that I might be able to sort of wade through my feelings and emotions and when I do meet that person who is right for me, everything will fall into place. I'm sure most details of those dates have escaped me by now, but I will try to remember to the best of my ability.

Admittedly, when I first started OLD, I was looking in all the wrong places. The first app I used was primarily known for hooking up, which is likely why most of those dates never went anywhere except the bedroom Although I did meet a few people that I am still friends with on the app, I should have never attempted to find someone looking for a relationship. More recently, I've used a legitimate dating site and quickly noticed that the quality of my dates increased substantially. I will probably abbreviate or change most names for the sake of anonymity, but I'll try to keep it simple so it doesn't get too confusing!

Date 1: Ben

Ben was the first person I ever agreed to meet in person. At this point, I believe this date was just over two years ago. He was a successful consultant for one of the top firms in the city. Ironically enough, my company was working on a project with his, and I was the main point of contact with his boss. Funny how coincidental life can be sometimes.

We spent several days, if not weeks before our first date chatting and getting to know each other. He playfully made fun of me for being nervous to meet him as I had admitted to him that I had never met someone from the internet in person. I had high hopes as I had enjoyed our conversation so far. (I have since learned how important it is to not place too much importance on someone before you have your first, second, and third dates, lol)

We ended up meeting at a wine bar on a Saturday night. I went shopping for a new pair of black boots and found a nice pair with a heel. I can see them in my closet from where I am typing this and it's making me laugh, thinking back to how nervous I was and how much I prepped for this date. I borrowed a shirt from my roommate and felt confident that he would like me in person.

Our date went well enough, from what I can remember. We finished the bottle and split a flatbread. After a few hours at the wine bar, he invited me back to his place for another drink, and I accepted, knowing what his intentions were. He conveniently lived only a couple blocks down the road and I followed him there, texting my roommates his address, just in case

I remember being slightly weirded out at the fact that he put on super trance-y electronic music. Looking back, this was probably the first major red flag, lol. Either way, I figured I should get some fun out of the date so I did and then made my way back home. Ben texted me before I even made it home to let me know that he had a great time and wanted to see me again. I decided I wouldn't mind it either, although I wasn't necessarily feeling that it would go anywhere.

Ben had a business trip to Canada the following week, so we didn't talk too much during the week. He did text me a few times, even going so far as to say that he wished he could have taken me with him. He sent me several pictures of the area where he was staying and we made plans to meet the coming Friday.

I forgot to mention how attractive Ben was in my first post. He was around 6'1, fit, with light brown hair and green eyes. Definitely a winner in the looks category. Normally I would feel that someone like him is out of my league (I know, I know "leagues" aren't a thing, but I do feel that people generally end up with significant others who are similar in attractiveness), but his nerdy-ness outweighed his looks and I felt comfortable around him.

When Friday rolled around, Ben asked that we stay in as he was exhausted from his trip. Naively, I said yes, and went over to his place. I met his roommate, and we chatted for a few hours. I left around midnight and texted him this time, to let him know I enjoyed spending time with him again. He responded right away, but I never heard from him again. On to date #2!

Date 2: O

After Ben, I decided that OLD had left a bad taste in my mouth and I disabled my account. I focused on work (I had 2 jobs at the time) and my social life. I was 23 and was still into going out for drinks every weekend with friends. I was interested in a guy I met through a friend; he was Egyptian and super handsome. I was intrigued by his heritage and how intelligent he was. In fact, I ran into his profile on the OLD app I was using before I disabled my account, and he sent me a few flirty messages. At the time, I thought he may have been into me too, but now I realize that he was only trying to make things less awkward by acknowledging the fact that we were both using the site. I certainly looked forward to hanging out with him & our other friends every weekend, but nothing ever came of it.

After a few months of not dating, I decided to reactive my profile. I'm sure there were a few promising conversations that were started but never led anywhere. I received a message from a guy whose page I had "liked" (admittedly) solely on the fact that he had the same name as my favorite basketball player. We clicked immediately and were soon messaging non stop. He lived about an hour away from me, but our profiles had linked up because his brother lived in the same city as me and he visited almost every weekend. O was from Russia but had lived in the US since high school. I guess I have a thing for ethnic men? Again, his culture intrigued me and I was hooked from the beginning. We exchanged numbers and began talking on the phone. The first night O called me, we talked for over 4 hours, taking turns asking each other questions.

We agreed to meet two weeks after we first began talking. He drove to my place and picked me up for dinner, and I was incredibly nervous to meet him. My first thought was that his pictures on his profile were not very accurate. He was much heavier in person than in his pictures, although that was certainly not a deal breaker for me. We drove to a nice shopping/dining area in the city and had dinner at a place neither of us had ever been to before. I don't remember it being awkward or uncomfortable, although I don't remember what we talked about either. It must have been a fairly unstimulating date, but I agreed to see him again.

If I'm being completely honest, I don't remember exactly how long I continued to see O...I would guess somewhere around 2 months or so. I liked spending time with him, but there was never really a spark. He often wanted to stay in and watch movies or play video games which is probably why it is a blurred memory for me now. I felt like I was settling, but at the same time, didn't necessarily want to break things off.

As much as I hate to admit it, one reason I was feeling a little uninterested in O was that he was certainly not well endowed but also that he seemed a bit inexperienced. I'm at the point in my life where the idea of teaching someone what to do in bed does not sound like a good time to me. I feel shallow just saying that, but hey, different strokes for different folks.

O and I had a movie date several weeks into our fling, and he was making me uncomfortable by rubbing my leg all the way up to my pelvis. I thought it was kind of a childish move to make in a theater full of people. I asked him to stop, and his response was "I can't rub my girlfriend's leg?" To which I responded "I didn't know I was your girlfriend". He immediately backed off and became distant.

The next day I didn't hear from him at all. When he finally texted me, he said he had been in a car accident. I asked him why he didn't tell me sooner, and he said that he felt foolish for not being more cautious. He then proceeded to break things off with me. I felt hurt, even though I knew I did not want to be with him long term. I hated that he called me his girlfriend for the first time, and then two days later felt totally different. I'm sure my response to his comment turned him off to me, but in all fairness, we hadn't even talked about being exclusive yet. It's unfair to assume you are in a relationship with someone without first discussing boundaries or goals or expectations, right?

Several months down the road he messaged me saying that he missed me and wanted to see me. I turned him down. I just couldn't see myself developing feelings for him a second time. I still look at his Facebook page every now and then to see how he's doing, but that chapter of my life is definitely closed.

This week has been incredibly busy. Went to a concert Tuesday night, hung out with some friends last night, and had a work event tonight and I"m just getting home. Looking forward to having a pretty lazy weekend.

I can't wait to post about date number 3...he was an interesting character for sure.

Date 3: Zach

The only word I can think of to describe the events that occurred with this person is....whirlwind lol. I don't specifically recall the beginnings of our conversation, but I do know that he messaged me first. I remember thinking that Z was cute in some of his pictures, but his hair was so crazy in that curly blonde afro way that I couldn't really tell. I could see, however, that he seemed like a fun person. He was fresh out of college and had taken the entrepreneurial track with a few of his friends. I thought it was cool that he was a little more unconventional than other people I had met.

The conversation must have started the week of July 4, 2014. I do remember that part, because I had plans to go out of town to a friend's lake house for the weekend, and we joked about him tagging along. For the first few days before I left town for the weekend, Zach and I were texting non stop. He would call me at night and tell me that he missed me, but that he knew it was weird to say that considering we hadn't even met yet. I knew what he meant, though. We became Facebook friends and connected on Instagram. We talked about our past relationships and what we were looking for. I should have known that this "relationship" was doomed to burn out just as quickly as it lit up.

Zach and I had our first date on the Sunday afternoon that I returned from the lake house. We met up at a local dive bar for a drink and to play pool. The bar was also serving chicken and waffles, so we ordered a plate to share. Considering how excited he was to talk to me before we met, he was certainly quiet and reserved in person. I thought maybe he wasn't into me in person. I wouldn't consider myself super overweight or obese, but I am taller than average, and curvy, and I know that's not everyone's cup of tea. [i always make sure to put recent pictures, both full body and face pictures so I don't misrepresent myself] I was a couple inches taller than him so I thought that might have made him uncomfortable. Either way, I found him attractive, and he had that bad boy edginess to him that is oddly irresistible.

After a few hours, we called it a night and said goodbye. He messaged me that night and said that although he wasn't sure it would work out between us, he wouldn't mind giving it another shot just to see if we had chemistry on a second date. I should have had the self awareness to say no to this offer, but I was in a bad place at this point in my life, mentally, and desperately wanted the attention.

Later that week, Zach suggested we meet up for dinner. He asked that I meet him at his place so we could ride together. When I arrived at the address he gave me, it was a very nice house - he lived in the garage apartment in the back yard. I went upstairs and inside and felt like I was back in college, except this place was worse than a dorm. We sat in his living room to chat a bit before deciding on a place to eat. During this time, he mentioned the following details he failed to leave out during the first week of conversation:

1) His student loans had been in default for over 6 months.

2) He had no driver's license due to a recent DUI.

3) He dropped out of high school and lived on the streets for a year before getting his life "back together" and going to college.

4) He was addicted to at least one illegal substance.

When I offered my opinion on these things, he quickly stood up and angrily asked me to leave, telling me he knew it would have never worked out to begin with, because he was more into girls who didn't have their $h!t together. I kept looking over my shoulders as I walked downstairs to go to my car. I had a strange feeling that he would have pushed me down the stairs at a moments notice.

Later that night he sent me a message on Facebook telling me that a family member had committed suicide and he found out after I left. He said he wanted me to come back over, but that was a "girlfriend duty". Psh.

Again, in retrospect, I should have seen the bright red flags waving in my face before we even met for our first date, but sometimes we just get overpowered by desire, especially when it feels like it's in reach.

I am on cloud nine right now. While I wanted to keep this journal in chronological order, I really want to document something that was said to me tonight.

In short (I'll go into more detail once I am caught up on all my stories), I'm currently seeing someone who has, so far, surpassed all of my expectations. He goes by Aaron. If I were to make a list of all of the qualities I want in a partner, he goes above and beyond in every category. He has a way of making me feel so comfortable, and I love his general existence. It's only been a few months, but I already know I am falling in love with him. He is different from anyone I've ever met and makes me feel something I've never felt before. It's cliche, but this is different. On the night of our third date, I called my best friend and told her that I had met my husband. I've NEVER said or felt anything even remotely close to this level. Call me crazy, I can take it

Last weekend, Aaron and I talked about our most recent relationships. I'm not a huge fan of talking about ex's, but I understand that it's important to know where your partner left off and how serious it was. I explained to Aaron that I was blindsided when my ex (H) broke up with me for HIS ex, because we had a fantastic relationship. I did admit that in hindsight I should have seen the red flags because H frequently brought up his ex girlfriend in conversation. Even the first week we began talking, I remember that he brought her name up multiple times. That seemed to be pretty consistent throughout our relationship, but I was naive enough to give him the benefit of the doubt. They'd been pretty serious, and lived together in a house he bought for the two of them. H's full story will be coming up pretty soon; hopefully this doesn't get too confusing.

Aaron's told me that he and his most recent ex had been together for less than a year, and although she was a great person, they just didn't have the chemistry to maintain a romantic relationship. Ultimately, she ended it.

All of that being said, I have noticed that Aaron has brought up his ex girlfriend in conversation multiple times as well, and I've always been cautious because of that. I've grown tremendously over the past couple years when it comes to dating and what to look for, so I had no plans of ignoring potential red flags. At this point, it's too soon to confront him or make a big deal out of it, but prudent to keep a mental note.

I received a text from Aaron tonight which said that he had been thinking about our conversation from this past weekend and after I told him about my ex, he will stop bringing up his ex girlfriend in conversation so that I don't become worried over that happening again. He reiterated that they are completely over and that he would hate for me to worry over something that is a non existent issue.

I appreciate that more than I can express. Like I said, I never confronted him about it, so he had no idea that I was even thinking that. This isn't the first time that he's done something like this, and I just think it's incredibly thoughtful.

Another incredibly busy week. Started a new job and moved to a new (bigger and better) apartment. Life is good.

A and I found ourselves in a tough position this week, where we both had car trouble at the same time (we were together when it happened). He got pretty frustrated but I stayed calm and helped where I could. He knows a decent amount about cars, so I mostly stood back while he worked on both cars. When everything was fixed, he thanked me over and over for being patient and helping out, and apologized for getting frustrated. This was the first time in our relationship where there was a potential source of conflict/stress and I'm glad it went over smoothly. I feel that if you can work together as a team rather than get upset with each other, it's a good sign that your relationship is in a good place.

Had a nice end to the weekend. Spent some time with A today. We talked about me meeting his close friends that he's known for years. I've met a couple of his friends already, but not this group. He told them about me already and that makes me happy

Date 4: Stephen

Stephen and I met through my roommate; they had been friends since high school. I was immediately attracted to him (think tall, dark, and handsome), but disappointed that he was more into pot than actually having a job. I should also mention that Stephen was a little over a year younger than me. Not a huge difference, but it existed nonetheless. I never intended to date him, but he started showing interest pretty quickly, texting me daily and making any excuse possible to come over and hang out with my "roommate". It didn't take long for him to ask me out and I agreed to give it a shot.

If I'm being completely honest, I kind of did the fade away to Stephen. I decided I wasn't interested in anything more than friendship, and so I just stopped responding so often. It didn't take long for him to get the hint. He actually began messaging me again about 6 months ago, and asked me out yet again. I told him I'd go out with him only as friends.

I think if he was a little bit more motivated in life and more mature, I'd seriously consider dating him. The timing just wasn't meant to be, though.

If there's anyone out there who happens to be reading this, I need advice on how to handle an upcoming event and would appreciate any input you all have.

I am going to a wedding that is across the country next month, and would love to bring the guy I've been seeing, who I mentioned in a few posts above. He knows about the event, but I have not asked him to come with me yet. I don't know if it's appropriate to even consider asking him at this point, though.

He would need to take a minimum of one day off work (but probably 2). If I ask him to come with me, I would pay for his flight, as I feel that it would be the right thing to do. By the time the wedding rolls around we will have only been seeing each other for less than 4 months. Also, I'm in the wedding party so that puts a little more pressure on me. (I have spoken with the bride about this multiple times and she's encouraging me to bring him)

All of those factors just make me nervous to ask him to be my date. There won't be any of my family there, just old college friends, so it's not like there will be pressure from that factor. I have to make a decision in the next week - thoughts? What would you do in this situation?

I forgot to mention something. Even though we've only been seeing each other for a few months, things are absolutely fantastic. We have great communication so far and are on the same page as far as what we want in a relationship. He's even mentioned things that he would like us to do next YEAR. So, my question isn't stemming from insecurities on that level, but more so from the fact that I'm afraid of rejection lol

I would ask him. It's not like it's your sister's wedding and all your family will be there. If he says no, no big deal. Not everyone feels comfortable around new people and when you have to take a couple days off work, too.

Thanks MM! I'm getting positive responses from friends - I think I'll go for it!

Another busy but fun weekend in the books. Did some volunteering and met a few more of A's friends. From what I hear, they liked me, which is great because I thought they were awesome!

So I finally worked up the nerve to invite him to the wedding, and he said yes! Now I'm a busy bee, planning fun things for us to do while we aren't tied up with wedding festivities.

That's good to hear ms!

Thank you! this will be our first trip together so I'm certainly looking forward to it!

Posting here so I can avoid becoming the crazy girlfriend and texting him again this morning.

About 6 weeks into dating A, I woke up from a dream that was very unsettling. I dreamt that even though things were going great with us, that he was still actively using his online dating profile (where we met). I woke up feeling hurt and confused (you know, how dreams sometimes magnify emotions, lol). In real life, I had disabled my account about 2 weeks after meeting him because I was so confident that I didn't want to see anyone else. As much as I wanted to keep myself from doing this, later that morning I reactivated my account just to ease my mind that he wasn't actually using the site. When I logged on, he was online at that exact moment. It really hurt my feelings, but I knew I had to approach the situation carefully because we hadn't actually talked about being exclusive at that point. I knew it wasn't "right" for me to get upset if the boundaries hadn't been established. I texted him later that week to tell him that I was not interested in seeing anyone else, and his response was that he wasn't interested in seeing anyone else either, and that he was excited to see where this goes. I left it at that and didn't mention the dating profile.

Fast forward a few months, and I had a very similar dream last night. As I've mentioned before, things have been going great and I have no reason to believe he's seeing anyone else. We spend every weekend together- he wouldn't have /time/ to date anyone else. I'm getting paranoid now because he texts me every morning to say hello (we don't have a long conversation, it's usually just a "morning, hope you have a good day" text). I haven't heard from him which is unusual. I even texted him about an hour ago. No response. I know I'm being hot headed and paranoid, but that dream is really throwing me for a loop. We have plans for tonight and last night he said he was excited to see me, so I really have no reason to be worried. Woof.

Still nothing...normally he would've texted me by now to see how my day has been. I'm going to hope that he just forgot his phone at home and that everything is fine. It IS Friday the 13th after all

Turns out he forgot his phone. I am SUCH a worry wart. It's kind of funny, thinking about how worried I was lol. It's so unlike him to go more than a few hours without reaching out to me, I was sure the worst had happened. Either way I had another great weekend with him after all. He mentioned that he had been keeping track of how long we'd been dating, and we reminisced about our first date for a short time. I don't know if this is what they mean by "when you know, you know" but this just feels so right. I've said that over and over and over but this feeling is something I've never experienced before. Sooooo looking forward to seeing where we end up

Intending to go back to the original purpose of this journal soon!