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Personal Recount of Online Dating Experience (LONG)

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I will preface this thread by saying that the following recounts are from late 2011. This is something I've been wanting to write about since I actively began dating in 2011 (4 years after divorce), but also wanted to allow some time in order to provide a more objective summary of my experiences. I'm unsure how many OT'ers use online dating websites to meet people but in my case it was absolutely necessary given my "work from home" status along with my responsibilities to my kids.

After being cooped up for the better part of 10 years, I was ready to get back in the dating game once Black Friday hit and was SCARED TO DEATH about meeting new people of the opposite sex and potentially starting a formal relationship with someone. I've been lucky enough to date a friend of mine since 2008 until the present. We still see each other off and on but it's not a formal relationship nor is it anything that would ever lead to anything serious as far as I can tell. I've NEVER introduced another woman to my two children (they're 10 1/2 now) and don't think I ever will. I'm unsure if that's correct or incorrect, but it's just the way that I am and I've found that I'm becoming more set in my ways now that I'm pushing 40.

Anyway, I hope some of you will find this enjoyable or can at least relate to the experiences...

June 2011 - A New Era In My Personal Life Begins

I simply couldn't take it anymore. Spending the vast majority of my time working at home from a computer in front of my kids and limiting myself to a small circle of friends had finally worn so thin that something had to change. My social skills had eroded over the years. This wasn't online poker or my job's fault as much as it was my own fault for not taking the time to meet new people. So with a credit card in hand I made the leap and signed up as a premium member to an online dating site after having filled out a free profile a few days earlier.

I didn't know what to expect but was desperate enough to actually go out on dates with people I had never met. This in itself surprised me, as I had led somewhat of a hermit-like existence after I found online poker and stopped teaching classes in companies here in Mexico City. With my profile page completed, all I had to do was to send informal "Likes" (or whatever you call it) to the women whose pictures I found attractive and see if they "liked" me back or sent a private message. I was 36 at the time and was looking for women between the ages of 35-42... wow did things turn out differently than I expected!

I admit that I was surprised by the amount of positive "likes" I got to my profile page as well as the amount of personalized messages that were being sent my way. Sure... five to ten messages per week may not seem like anything to a 20-something who's extremely confident and comfortable around members of the opposite sex, but I had forsaken pretty much all social contact for a long time due to marriage, then divorce, then health problems, then my priorities as a father. It seemed like I always had a great excuse for not connecting in person with women... even if I found them attractive and was interested in talking to them.

Late June 2011 - My First Date

My first date was with a woman who claimed to be 43 years old (7 years older than me at the time). She was kind enough via PM and even called my apartment to confirm my identity. When one of my kids answered the phone, she said that "gave her the confidence" to go out on a date with me... lucky me I suppose.

That evening I dropped the twins off at their mother's house, put on some nice clothes and cologne and headed out. We set up a time for me to arrive at my date's apartment and I got there about five minutes early, paid the taxi driver, stepped out and rang the appropriate buzzer. She didn't respond and I was actually feeling relieved that I might find a way out of this "stupid idea" and just go home and continue with the routine I had enjoyed for years. After about a minute of waiting at the apartment building's entrance, my cellphone rang and she explained that she was on the phone with her son. She would be down as soon as she hung up with him.

About 10 minutes later, I was still waiting at the entrance and it began to rain... hard! Not knowing what to do I seriously considered simply leaving but then told myself that if I chickened out it would just be another excuse. Thirty minutes after I arrived, I got another phone call from her stating that she'd be "right down" so I stayed under a covered part of the building to avoid getting wet (I hadn't brought an umbrella) and decided to wait just a bit longer. That turned out to be 45 minutes from the time I arrived. The woman who greeted me at the building's entrance was not as attractive as the pictures I had seen (which I estimated had been taken 5-10 years earlier), but the point of meeting new people was to practice/improve upon my social skills so this wasn't a big deal to me.

However, there was something definitely "off" from the moment I laid eyes on her. For one, she couldn't walk for ****! She was wearing a normal dress with high heels and was constantly tripping and stumbling around to the point where I was sure she'd bust her rear before we ever got to the parking area. Her voice was also horrible... it sounded exactly like the 1980s version of Sesame Street's Cookie Monster and I couldn't really understand what the **** she was saying half the time.

Honestly, I was expecting a polite apology when she greeted me, but the first words out of her mouth were more like chastising me. "You'll have to excuse me, but it's very important that I talk to my son." It wasn't the words but the way she said it. She decided that we'd take her car and that we'd go see the Harry Potter movie at a mall about three blocks away. Thankful that the date was finally underway, I accompanied her to her vehicle and slipped into the passenger seat.

It didn't take long for me to realize that her driving was worse than her walking! She was obviously horrible at driving a standard, and getting out of the underground parking area took about 5 minutes. The drive to the mall should have taken less than 5 minutes, but it was more like 20-25 because she "got lost." All this time, she was telling me stories about how popular her profile was on x-dating site, and how men are trash and just want one thing, and about her job helping out kidnapping victims, and about her ex-boyfriend, and about how she only decided to go on a date with me because a kid answered the phone when she called, and about how Cablevision sucks (more on that shortly), etc.

Although we had originally agreed to meet at 7:30pm, it was now about 8:45 when we finally got to the mall. Immediately after she reached the mall's underground parking area she stopped (not worried about the vehicles behind her waiting to get in), got out of the car, and began rummaging through her trunk. I fought off the urge to make a run for it (as that wouldn't be the mature thing to do, I told myself) and waited a good two minutes for her to get back behind the wheel while the cars behind us were honking like crazy. She had retrieved a plastic bag and inside were a bunch of cable boxes and remote controls. I was sure she'd give me an explanation (and unfortunately she did - without moving her car forward). You see, she had broken up with her boyfriend recently and he ordered a bunch of adult movies, and he's a piece of ****, and she's a poor victim, and men are trash, and she hardly watched HBO anyway, and...)

I interrupted with, "Would you like me to park the car?" I thought to myself, "I may be a donkey when it comes to dating but I can drive a stick shift!" Thankfully she said yes and I got out and walked around as she moved over to the passenger seat. I backed into a nearby parking spot and got some obscene whistles from a few drivers who had been stuck behind and were passing by as I parked. She got out WITH HER PLASTIC BAG OF CABLE BOX GOODIES and explained that we would be going to the Cablevision store to settle her bill before the movie. Already dreading how long this was going to take and how much of a show it was going to be, I forced myself forward alongside her, telling myself that if I could survive this then it would make for a great story to share in the future.

After walking about 10 yards towards the underground mall entrance, it was painfully obvious that she was having trouble standing up. She wasn't drunk, but she obviously wasn't accustomed to walking in high heels. The next words out of my mouth were obvious, so I politely asked, "Would you like me to carry the bag?" She said, "Yes, thank you." By this time, my attitude has changed slightly and I felt a mixture of pity and laughter as I couldn't believe what I was experiencing. Anything was better than the initial anxiety I had felt about going on first dates so I was gaining confidence even as I was also dreading spending more time with this person.

Due to her walking, it took us a good 15 minutes to get to the cable store. She had stopped talking so much and was focusing more of her energy on not falling down. Of course the store was closed by the time we got there. Not wanting another 15 minute walk of about 150 yards, I offered to walk back to her car alone and place the plastic bag inside while she waited. More than anything this was a way of forcing myself to stay on the date because I knew that I was capable of splitting any moment, but that I wouldn't do so while in possession of her keys (which weighed more than a fully loaded janitor's ring). She agreed and I was back with her in a couple of minutes.

So now it was time to "go to the movies." She apparently had caught her second wind as we meandered our way through light crowds and attracted stares as she attempted to get on board the first escalator. It was seriously like watching a cat pawing at something in a puddle... knowing that she's going to have to commit in order to get at whatever but not wanting to get wet. People were REALLY staring now, as she kept talking and slipping without any consideration for other people on the escalator. By the time we reached the top floor, I told her I would pay for the movie tickets and that she could wait nearby while I got in line. She was okay with this and I left her seated by the theater's food counter.

I had a stroke of run-good when I got to the ticket counter, as the Harry Potter movie would be starting in just 10 minutes! However, when I walked back to the area where she had been sitting I didn't see her. By this time the charm of having a good story to share had worn off and I was running through different scenarios in my head as to any negative consequences that might come from me making a run for it. I came to the conclusion that the worst that could happen was she'd call my apartment, send me nasty messages on my cellphone and troll my online profile page. All things considered it was ultimately +EV to GTFO so my mind was made up...

Then I heard a commotion about 30 feet away. Someone at the head of the hot dog/sodas line was yelling obscenities in a cookie-monster voice at a cashier and wouldn't you know it... it was my date! I have no explanation for why I walked over except that people must have recognized me from a few minutes earlier and were staring directly at me... wondering how I was going to react since I was the person who had arrived with her.

I walk shamefully toward the counter and a pleasant young woman greets me with a smile and says, "Good evening. I was just explaining to this woman (referring to my date) that she must wait in line like everyone else and she will be waited on as soon as it's her turn. However, we've decided she's a 'special case' and we're going to take her order now. I hope you enjoy your movie!" I felt about two inches tall as another cashier slid over a hot dog and soda while my date handed over a bill and received her change. The line behind her was about 50-people deep. I wanted to cry.

"Do you have the tickets?" she asked. She handed me her hot dog and soda and accompanied me towards the theater area. We passed an area where people were leaving after a movie had finished. All the couples seemed so happy. I fantasized that I would give anything to be walking about at that moment with ANYONE other than the person I was with. All the women looked so attractive (even the 70+ year old grandmothers) compared to the hag I was walking with.

I weathered more stares and more stumbles as I handed over the tickets, received the 3D glasses and deliberately walked to the very top row and sat down as far away from anyone else as possible in the half-filled auditorium. The previews/trailers had begun and my date hadn't stopped complaining about bad service at movie theaters, about how excited she was to see Harry Potter, about how great 3D movies are, about how important her son is, about how her cellphone has been acting up, about....

Suddenly a woman who had just sat down with her boyfriend/husband a couple of rows down got up, looked straight at my date and gave the most ferocious SSSSHHHHHHHHHHHHHH I've ever heard in my life. I recognized the couple as being next in line at the food counter when all the nonsense was going on. Her boyfriend/husband had also turned around and stood up by this time as if they were going to call one of the theater's employees to shut my date up, but suddenly the hag was at a loss for words and became 100% focused on rummaging through her purse! The 30-something couple then looked my way at the same time and smiled and I smiled back at them and shrugged my shoulders. I could've hugged them for that!

The movie was uneventful and it wrapped up. We walked out of the auditorium, handed over our 3D glasses and then the blabbering resumed. It seemed that my date had lost her cellphone and now we would have to wait for one of the employees to go back inside the auditorium and search for it. By this time I was flat out exhausted and couldn't even muster eye contact as she rambled on about how important her cellphone was to her, about how people will steal things from you instead of give them back, about how late it was, and so on. Luckily the employee found the phone quickly and returned it to her, and we made our way to the lower levels of the mall. There were very few people remaining in the mall to see us now and I was realizing that this night was FINALLY going to come to an end. She mumbled something like "I won't be able to drive you home." I replied with, "There's a taxi stand right outside. It was nice meeting you." She said likewise and we parted ways.

A half-hour later I got back to my apartment and it was close to 1:00am! My kids' nanny (who is about 65 years old, had been urging me to go out on dates, and is also the apartment building administrator) knew I was going to be out that evening and had taken the liberty of spending hours cleaning up the place. I was happy to see her, as she has been somewhat of a second mother to me for more than a decade. I was hungry as hell when I got back and she offered to make pancakes and coffee. We sat in the living room and laughed at my recollection of the events that had transpired until the wee hours.

The final contact I ever had from that first date was around 1:00am when I got back that evening/morning. "Hello David. You seem like a nice guy but I'm afraid we don't have anything in common. Good luck with finding someone."

Meeting New People: Second And Third "First" Dates

Nothing could have prepared me for that first date, but it was invaluable in that it made me look forward to meeting new people because I couldn't imagine any scenario being as unpleasant as the first one... and I was right.

My second date was arranged at a coffee shop with a 33 year old woman (3 years younger than me at the time) whose picture I had liked. We noticed each other and sat down and ordered something to drink. It was immediately obvious to me that I would not be going out on a second date with this person either (again, the pictures I had seen were obviously taken years earlier), but she was pleasant enough and she politely asked me what I did for a living. I explained to her that I work from home via a computer on the Interwebz and explained that I had been working on a lot of WordPress projects since Black Friday.

She didn't grasp any of this and said as much, so I decided to return the favor and inquire about her work, etc. Unfortunately this hit a nerve and what came out was a very sad story about a co-worker who was an ex-fiancee, a miscarriage, and a broken heart. I felt absolutely zero animosity towards this person as she was telling her story because it was so obvious she was hurting. I listened, said I was so sorry, and told her she was welcome to contact me if she ever needed someone to talk to. We parted ways and I left with a positive attitude coming to terms with the fact that everyone has their issues, doubts, fears, etc. I never heard from her again though.

One day later, I was again going on a "first date." We agreed to meet at a 24-hour restaurant inside a mall that was about 15 minutes away for both of us. It had decided to rain once again and I actually arrived 10 minutes late. This new woman was 32 years old (4 years younger than me at the time), never been married, and apparently had a cozy job with a major bank. She had sent a text that she was running late as well so I decided to go walk around a bit. Although she was quite a bit shorter than I was, she actually resembled the photos I had seen once I spotted her. We greeted each other and sat down to drink coffee and talked for about 2 hours. This was a great thing for me and made me feel extremely comfortable. Just imagine, I had been SO apprehensive about going out on dates just one week ago and now I was sitting down and having a pleasant conversation like a pro!

I enjoyed that date and we actually went out one other time, but it wasn't nearly as fun for me. She was much more serious on that second date and told me she'd like to walk around outside and look at houses - as this was something she thoroughly enjoyed. I must admit that hearing her talk in depth about House #1 and House #2 was somewhat interesting, but that she had lost me by House #5. We sat down on a bench at a nearby park and she began telling me very personal things that wouldn't add anything worthwhile to this story. Suffice to say she'd been through some rough experiences, was deeply saddened, and that would be the last time I saw her.

... continued in second post ...


* 2011 I was ready to start dating again - tried online site

* Had a REALLY bad first date (details above)

* Dates gradually started improving, as did my confidence

* I become comfortable going on "first dates"

* I meet some cool people, form a relationship, then decide it's best to be single after all

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... continued from first post ...

Fourth "First Date" - Turning The Corner (July 2011)

Although I hadn't been on any date that even passively resembled what I had in mind when I signed up for a premium online dating service, I was getting much better by this time at communicating with potential dates beforehand. There was this one woman who I had been chatting with online, had accepted a Facebook friend request from, and was getting along pretty well until I took ~20 seconds to reply to one of her instant messages. This set her off into one hell of a fit about how I "must be a 'player' using my premium account to chat with several potential candidates at one time." Actually, that was exactly what was happening (excluding the "player" part). I blocked her and started feeling much better about myself immediately. I had come a long way since my first "first date."

So the fourth date was at another coffee shop, and the woman was about my age. At the time, my kids were close to 8, but she had only one daughter who was 17. I enjoyed talking with her for about an hour and then we agreed to go out to the movies later that week. The movie we saw was that Woody Allen film (Midnight in Paris?), which I enjoyed. As we were sitting in the theater, she slowly started edging toward me and I was becoming aware that she might be coming on to me. The bad thing was that I was coming to grips with the fact that I wasn't really attracted to her. We finished watching the movie, went back to her car, and she went out of her way to drive me back to my apartment (if it hasn't become apparent by now, I don't own a car - it's not really necessary here in the big city and not having one gives me more money for my kids, etc).

So we talk in her car for about 10 minutes outside my apartment and I'm getting a vibe that she may be interested in me inviting her up. That didn't happen. The next few days, she started sending me a bunch of emails that were imo overly positive (something I can't stand) and then took it upon herself to start dropping lil' bits of advice on how I should be raising my kids (something I REALLY can't stand). Although that friendship didn't work out, it marked the first time in my online dating experience that someone probably wanted to form some type of relationship (albeit casual) with me, and I was boosted.

These Women Like Me? Really?

This is a bit personal, but I was never really that popular in high school aside from the public address announcing stuff I did for our basketball team. I wasn't really that attractive either... pimples and bad hair days did a job on my confidence. However, when I got out of HS and started going to college (I think I officially have 5 college credits out of all those classes -- 4 for Spanish and 1 for Orientation), things CHANGED. All of the sudden I was sitting in these classes and getting HIT ON by women... good looking women! Sure, there had always been an occasional girl in HS who was into me but I was pretty embarrassed about the whole thing. However in the small town college I was attending there were girls ranging from my age to their 40s going out on dates with me, calling me for tennis lessons, making excuses to talk me into "study sessions," setting me up with their cute friends, complimenting me on my looks... it was surreal!

Fifteen years later (by the time I had begun dating online), I had pretty much assumed that whatever good looks I may have had in the past were way behind me after marriage, kids, divorce and just overall responsibilities. But with each date I was sensing that at least some of these women were into me, and it was refreshing.

One of my next dates happened to be at a Starbucks in a mall and we hit it off. She was 24 (12 years younger than me at the time), had a 5 year old daughter and her own insurance (affiliate) agency. We began going out more and more and she finally told me that she was interested in having a formal, long-term relationship with me. All of this happened within two months of my very first online date and I wasn't quite ready to move in that direction.

There had been tell-tale signs that things may not work out between us and there was also a scene she made at a school supplies store when they insisted that anyone who enters had to leave the shopping bags in a locker. She also was insisting that her daughter and my kids meet each other (I hadn't even introduced HER to my kids)... was making ALL kinds of crazy-ass plans, and that was a step I definitely wasn't ready to take. It all came to a head rather quickly (thankfully) when she started offering her advice on how I should raise my kids. We parted on not-so-friendly terms, did the customary un-friending via social media, and that was the last I heard of her.

Sixty Days After My First Online Date - I Meet Someone Special

"First" dates were coming naturally to me by now. I had probably been out on more than a dozen of them since that memorable experience with the hag. I met the next girl when we had our first date at TGI Fridays and immediately hit it off. As a matter of fact, I was crazy about her from the first date. She was 26 (10 years younger than me at the time), a doctor in her first year in a hospital's Obstetrics and Gynecology residency program, was smart, sweet, attractive, and all that good stuff.

We went out on several dates, each one bonding a little more closely and it wasn't long until we started a relationship. Whenver my kids were with their mother, she'd stay over at my apartment or vice-versa. She was great and best of all was really not the kind of person to give someone else advice on topics she couldn't directly relate to (she had no kids).

We had fun, but then the pressure started being applied when she began insisting that I spend more time with her. Obviously, I had always been up front about being a dedicated father and having a boatload of work to do - and that those priorities would come first. I couldn't really blame her though... her reasoning was very logical. She only got one weekend off per month and she expected me to give her more attention and spend more time with her during those weekends. Fair enough... but it was starting to stress me out.

Then, it started becoming extremely obvious to both of us that the next step in our relationship was going to be me introducing my new girlfriend to my kids. I have to be honest, I REALLY considered it. And almost did so. She was that decent imo... but I just couldn't bring myself to do it, so things quickly fell apart after that.

We stopped seeing each other after about three months and she eventually went on to meet someone special and they are now getting married. As for me, those few months that I spent dating were not a bad experience at all. Since that relationship ended, I haven't gone out on many more online dates. A workload came in around that time and luckily I've been pretty busy between work and kids for the past three years since Black Friday.

Anyway, that's my story. It's not all that entertaining but I did want to share my experiences just in case someone who is shy about meeting new people can relate. If anything, I believe that anyone who consistently goes out on "first dates" will eventually see himself in a role similar to that of Deuce Bigalow.

Thanks for reading!


* 2011 I was ready to start dating again - tried online site

* Had a REALLY bad first date (details above)

* Dates gradually started improving, as did my confidence

* I become comfortable going on "first dates"

* I meet some cool people, form a relationship, then decide it's best to be single after all

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lol you guys are dicks.. although i can see your reasoning behind not letting a woman meet your kids, i feel like dating someone for three monthss should change your position on that one. if you liked the girl and had a good connection, just seems like its time to put yourself out there. as a poker player, obviously you trust your instinct/judgement but at some point your going to have to take the bold step.

4 years post divorce, you probably have had a lot of time to fix your deficiencies and better yourself as a person. Single parent, good job are good incentives to head in the right direction alone. idk, whatever makes you happy man but i would say don't be afraid to take that big step. worst case, you move on and continue to get stronger. another question is, has your ex wife moved on/remarried or serious relationship? just curious if she does have a significant other, have they met your children and how did that experience go? they are right at the age where this shit can kind of fuck with their heads so i appreciate the proceed with caution you are holding too

btw did you have any 1 night stands, or mostly the dating encounters?

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Quit reading after reading the part where OP waited 45 minutes outside for his date to finish up the convo with her son on the phone. I would have left after 10 minutes as I consider my time just as valuable as she considers her time on the phone talking to her son.

Other mistake was going to a movie theater as a first date. Unless you are just looking for a piece of ass, which you obviously arent and you might have exchanged a lot of emails/IM in getting to know each other, other wise, how in the fuck do you expect to talk to each other to see if you click in a fucking movie theater?

Rules to follow for online dating..

1) always agree to meet at a public place (other than meeting at a movie theater) for couple of reasons.. 1) if she is running really late or doesnt show up at all, there might be other women you could talk to. 2) If she doesnt look like the pics she has posted in her profile, you can cut the date short unlike being stuck in a theater or stuck at her place.

There is other shit I could post but you will learn as you go. One of the things you must do is DEMAND recent pics. It pisses me off when women have pics posted from 10 years ago and they are 50 lbs heavier now than they were 10 years ago.

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lol, bet she had an extremely hairy bush - but guess we will never fkn know as OP never gets to first base and if he does he doesn't know how to post pics

just as well i have a vivid imagination and the first girl was extremely hairy, the second one was extremely fat and had short arms and third one was bald

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Thanks for the replies. I anticipated the tl;dr posts and recognize they're deserved... just felt good to get my experiences out there - even if they don't make for much of an entertaining read.


I didn't have any one night stands. I certainly had those in mind when I originally signed up, but after I got a few dates under my belt it became clear that either I wasn't meeting the right type of women for those or I wasn't the right type of guy for those (probably the latter).

There were some other encounters that got past 2 dates, but they typically ended with the woman conveying interest in a formal relationship and me not pursuing that for any number of reasons.

LVpokerdealer & mesaplayeraz:

Yeah I know. It was lame and I shouldn't have tolerated that. I was nervous I suppose... but there's no excuse for that.


No pics. Sorry about that.


Yep! Bfactor's posts are much more entertaining than this one though.


I'm a whole 7 years removed from divorce now and things are going well. I'm fortunate to have the twins and plenty of work to keep me busy. The friend I've been seeing [edit: I said "for the past 8 years" but meant "since 2008"] is a big help. It's not completely ideal (when she calls I say yes 100% of the time and when I call it's about 50/50) but it's a good arrangement for someone like me who definitely isn't ready to "take the next step" - at least not now.

Anyway, thanks for reading. :)

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I got there about five minutes early, paid the taxi driver, stepped out and rang the appropriate buzzer. She didn't respond and I was actually feeling relieved that I might find a way out of this "stupid idea" and just go home and prepare a message to her demanding reimbursement for the taxi round trip

that's how the sentence actually finished in my mind.


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If you dont introduce a new women to your kids how are they supposed to know what a healthy or unhealthy relationship looks like? Part of growing up is learning from your parents action.s within their relationship with a Sig other. Kids respond to actions better than words. You can tell them to treat others well or not to accept bad people but until they see it in action they have no clue. There only going to learn the ins and outs of dating from their mom it sounds like or the movies (and you don't want that)

Anyway, you sound like a great father, maybe reconsider your stance on introducing women to your kids.

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