Confessions of a New Age Player

By Scott Edwards

I'm just an average guy who re-entered the dating world back in 2007 after being married for over 10 years with no clue about how much things had changed thanks to the Internet and online dating. To put it in perspective, from my high school years through my late 20s, I probably went on less than a dozen first dates. This was back when I was considered above average looking, had a full head of hair and a tight body. Fast forward, in my first three years as a divorced man in his late 30s / early 40s with a receding hairline and a few more inches around the waist, I went on over 100 first dates. The difference? Online dating! Once you get over the "Am I really so desperate that I have to resort to meeting strangers on a website?", it actually works.

Along the way, I would share my dating experiences with my closest friends, who found my adventures and perspectives in dating to be hilarious. Keep in mind that for the most part, I agreed to meet just about anyone that weighed less than me (yes, I'm shallow) and I'm not always the most politically correct person in the world. They found my stories to be so entertaining that they talked me into writing about them. The names have been changed to protect the innocent as well as save me from potential law suits and death threats. But they are listed in the order they occurred, and for the most part, I believe they illustrate a change in my personality over time.

And as a guy who has went on so many dates (no exaggeration...well over 100 in three years and still going), I've kind of got this thing down to a science. I provide tips for newly single people, and yes, I get the irony of someone who has went on over 100 dates in three years saying he has it all down. But while I'm very good at getting first, second and even third dates, I've never claimed to have the whole sustainment thing down.

• Language: English
• Publisher: Scott Edwards
• Release date: Apr 16, 2012
• ISBN: 9781476071800

Scott Edwards

Nothing Done in Secret is my first novel. I have a master’s degree in management and have worked for over twenty years leading engineering teams on NASA and other aerospace programs. This experience in science and emphasis on attention to detail were valuable in the process of creating a complex investigation plot. These years also gave me countless opportunities to observe human behavior under all circumstances.

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Confessions of a New Aged Player

(An Insider's Look at Online Dating)

Scott Edwards

Published by Scott Edwards at Smashwords

Copyright 2012 Scott Edwards

Smashwords Edition, License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to Smashwords.com and purchase your own copy. Thank you for respecting the hard work of this author.

PREFACE

In The Game, Neil Strauss reveals the world of the pick-up artist and explains the art of attracting women at bars. I believe everything he suggests really works in being able to get the attention of beautiful women, though I can't relate to having the confidence or desire to apply these skills. I also understand part of the underlying message of the book, that many of these artists get trapped into focusing too much on the game, and never build a solid, lasting relationship. To that, I can totally relate.

When I got divorced four years ago, I had no idea how to go about meeting women. Even though I hadn't yet read Mr. Strauss's book, it wouldn't have mattered...I've never been the guy that could walk into a bar and attract women, and could never apply the lessons I picked up from his writing. Maybe part of it was I had no desire to become a player. I suppose there’s also a touch of arrogance…why should a well educated, successful man have to compete with some douche bag wearing a big hat and lots of bling? Eventually I found that meeting people online is much different than trying to pick someone up in a bar, and that my natural personality was one that would make me a very successful online player, even though my intention has always been to find a relationship. Or at least that’s what I tell myself.

When I look back to my 20s, I was considered above average looking, intelligent, and well on my way to a successful career. Yet all told, I probably had less than two dozen first dates before my marriage at age 29. This of course doesn't include encounters in Vegas, because what happens in Vegas, stays in Vegas. Except for herpes. That shit'll come back with you (thank you to The Hangover for that classic line).

In contrast, during the first three years as a divorced man (starting at age 39) who was starting to lose his hair and could stand to take off a few pounds, I went on over 100 first dates. The Internet has made finding singles much easier, and the rules of attraction are much different than those that apply at bars. At the same time, going on a lot of first dates is not necessarily a good thing. I've had my share of strange women, and probably been described as less than perfect by many members of the opposite sex.

This book was written at the suggestion of a few good friends, who always found laughter at my adventures in dating. At first, this was nothing more than a compilation of dating stories, but along the way, I realized I was pretty good at getting the attention of desirable women. I won't flatter myself by thinking I'm the online version of Neil Strauss and his friends from The Game. But I do think I'm pretty good and some of my advice is bound to work.

For those that may think I’m kind of an ass clown for writing about the women I’ve dated, well, yeah, I am. In my own defense, about half way through this adventure, I started telling new dates that I was writing a book about my dating experiences. It’s their fault if they were stupid enough to believe it wouldn’t include them. Many of the women I met that resulted in more than one or two dates often shared very intimate details of their lives. This I respect and will draw the line at sharing too much information. Plus I have a lot of baggage of my own and believe that people who live in glass houses shouldn’t walk around naked if they don’t have a killer body, or something like that.

I’ve divided my writings into two sections. The first is a collection of my dating stories. The names have been changed to protect the innocent (and avoid someone wanting to sue and/or kill me), but the timing and description of events are pretty accurate. The second section is dedicated to tips for those considering online dating. I’m not one of those guys that has a method and not going to promise if you do what I say that you’ll meet the woman of your dreams. But I’m fairly confident that if you listen to some of the advice, you’ll have a better chance at getting dates. For those of you who do, good luck and be safe!

For Kristina – Thanks for helping me find what was missing.

SECTION 1 - THE STORIES

In The Beginning - October 2007

I did it. I filed for divorce today. Tell me I did the right thing. I was sitting in my car outside the lawyer's office. I had been there nearly a year to the day earlier but couldn't bring myself to sign the papers. I was miserable and trapped in a marriage with someone I didn't like, much less love. But I had three sons that meant everything to me. I knew what it was like to grow up without a father, and couldn't do it to them. Still, I realized they deserved to be around two loving people, not a couple that couldn't stand to be in the same room. And I'd still be there for them, that would never change.

The first person I called was my girlfriend from my early 20s, Kristina, who was also my best friend. I can't tell you that. Only you know. You know that I'll be there for you, and so will Ally and Asha. No matter what, you're a great father and your boys know it. This won't be easy but you'll get through it. Ally and Asha are Kristina's twin nieces. We started dating when they were two, and over 20 years later, they were my drinking buddies, as well as my little girls. I tried my best to be there for them as they didn't have a father figure and now, along with Kristina, were my support system.

I worry that I'll never meet someone, that I'll grow old and die alone. That's stupid, right? I'm a pretty good looking guy, successful, a great catch. Women will be fighting over me, don't you think? I was looking to Kristina for comfort, probably not the smartest idea considering she loved being a sarcastic smart ass, even at the most inappropriate times.

Well honey, your hands are really soft. You have that going for you on those lonely nights.

Looking back, I can say that filing for divorce is not an easy thing. Oh, the process itself is simple. Go to a lawyer. Fill out some paperwork. Sign the paperwork. Pay said lawyer a lot of money. I suppose if you can’t afford a lawyer, then there’s probably more to it. But making the decision to end a marriage after 10 years and three children with no idea of what the future would hold for yourself or your kids, that’s tough. I can say now that it was the right decision, but back then I was scared that I was making the biggest mistake of my life.

My reason for filing for divorce may or may not have been typical. Up until making the decision, I always figured 95% of marriages ended for obvious reasons…infidelity, abuse, financial issues, etc. None of these really applied to our marriage. We lived in what many considered a dream home - a 5,000 square foot house on a lake that we didn’t struggle to afford, neither of us were physically abusive or had alcohol problems, we were both faithful, and to the general observer I’m sure we seemed like the perfect couple. We had three healthy sons, belonged to an exclusive country club, no health issues for anyone, and both considered charming and easy to get along with. But I was completely miserable, and I’m sure she felt the same way.

I admit that shortly after filing, I started having some excitement about getting back into the dating world. My dating history had been somewhat limited, as I always seemed to be in a relationship. For most of my 20s, I dated Kristina. She is an obnoxious but really hot Asian chick who to this day I absolutely adore.. but she's always been a total control freak and a few sandwiches short of a picnic. We’d break up, but eventually get back together when she wanted to get laid…OK, when I wanted to get laid. Somewhere along the way, we realized we were best friends and that it really sucked when we were fighting, and finally decided never to date one another again (though we never agreed to stop having sex). After Kristina, I dated someone for two years who was probably the perfect woman for me…my family still talks about her and how incredibly nice she was, though timing was just bad I suppose. That and I’m an idiot. I broke up with her for the woman that would become my wife for 10 years, give me three incredible boys, mediocre sex every other month, and generally tell me what I loser I was every chance she had. My ex-wife is a very intelligent, beautiful lady but we were just really, really bad for each other. By the end of our marriage, we seldom did anything with just the two of us. Maybe a dinner once or twice a year without the kids, that was it. The sex was very bland. After our first child, who was born the 2nd year we were married, she decided that oral sex was something that parents didn’t do, and there was no debate. So for six years, no blow jobs, nor did I have any opportunity to ever have my lips or tongue explore anywhere beneath her neck. However, two years before our divorce, she forgot my birthday…for a few days. She was a complete bitch to me while I acted depressed, and the night she realized what she had done, she went to work down there like never before. My birthday is in December, and she got pissed when a few days after this glorious event, she asked me what I wanted for Christmas and I said for you to forget it was Christmas for at least a couple of days. That didn’t go over well. She didn’t have much of a sense of humor…either that or I’m not funny, or both.

My journey into the dating world began as an almost 40 year-old that hadn’t dated much other than three long term relationships. I wasn’t looking to make up for not having slept with many women, but I genuinely sought my perfect match, someone that I could spend the rest of my life with. As the concept of being available started to hit home, I had mixed feelings. I’m not much of a player, having zero game. I was almost 40, decent looking but still almost 40, and really wasn’t sure how dating worked in this decade, having been out of commission for over 10 years. No matter what Kristina suggested, I figured I was a good catch (and if not, my hands really are soft). While I’m not a guy that has women drooling over him, I’m in good shape, relatively handsome, make a very good living, witty, and am domesticated – I cook, clean, do laundry, cut coupons, and after 10 years of being married, no longer pee on the toilet seat. Yeah, there had to be some woman out there that would find me perfect and vice versa. So it began, my adventures in dating.

The first date, or How can you screw up something so easy?

November 2007 – San Francisco

As I’ve noted, I filed for divorce on October 22, 2007 and told my wife on October 31. In between I went to Las Vegas. It seemed fitting. Still does. As luck would have it, my company assigned me to a project in San Francisco for a few months, which allowed me to escape the house (she didn’t take the news so well) and digest what the future would bring. When I say luck, Kristina now resides in the bay area, and I knew of all people in the world, she’d be the one that would be there for me, listen to my problems, and tell me to stop being such a pussy and get on with my life. She’s incredibly sweet this way.

One night over dinner, Kristina told me she had a friend that she wanted to set me up with, Yuki, who was also going through her own divorce. She thought it would be good for two people in similar places to get together. In other words, she was telling me she was sick of listening to the two of us bitch, and figured it would be easiest on herself to introduce us so we could whine together. Sounded good to me. She gave me Yuki’s number, said she was expecting my call, and thus began my first date in over 10 years.

At first, I was nervous. I’d never had a problem talking to strangers, and am considered very witty by most. But for the past 10+ years, the people I had spent an evening talking with were not ones I was hoping to sleep with. Now, I was going to have to watch what I say. It occurred to me that I often talk about things that are on my mind, and right now, divorce was at the top of the list. Yet I knew that people didn’t want to hear about that, so I planned ahead with a list of topics that would likely prove more interesting. Since Yuki was Japanese, I could share stories of visiting Japan and impress her with my command of her native tongue (I speak Japanese at the level of a 1st grader with a learning disability…maybe not that good).

We met at a nice Italian place in the North Shore area. Yuki was probably what most people would imagine when trying to picture a Japanese woman…5’2" or so, 100 pounds, soft spoken, a little bit of an accent but easy to understand. While I tried to avoid discussing my divorce, she talked openly about her failed marriage, how she and her husband always fought, and how she knew divorce was the right answer but it was so difficult. She hated talking to her friends about her soon to be ex, because they would say bad things about him and she didn’t like that. She was happy to talk to me, and while we talked about divorces, we didn’t really bitch about our spouses (though I kind of wanted to). I did impress her with my limited Japanese, which was still more than what she was expecting.

I had a feeling that I had perked her interest, but wasn’t sure. Since we finished dinner by 8PM, I decided to test the waters by asking her if she’d like to go somewhere for a drink. While this wasn’t planned in advance, I later made it part of my routine. It’s actually a very good first date strategy. If you think the other person is interested but want to make sure, suggest continuing the date elsewhere. No, that doesn’t mean inviting them back to your place…well, not always. Because if someone is open to continuing the date, it means they probably like you. Or they are just really, really bored and have nothing else to do. In this case, Yuki accepted my invitation for an after dinner drink.

Since my hotel was close by and had a nice bar in the lobby, we went there though I knew that there was no chance of getting her back to my room. She took off her sweater and sat close to me and we talked for awhile. I wanted to put my arm around her, but was afraid she’d take it the wrong way. I could see she was vulnerable and didn’t want her to think I wasn’t sincere. I was the perfect gentlemen, and after our drink, walked her to the train station. She shook my hand, and when I asked if I could call her again, she politely said no, I don’t think that would be a good idea and left. WHAT??? Wow! What a shock to the system. First date in over ten years and shot down, no idea why. We had a good conversation, spent a few hours together, I was a perfect gentleman, so what was the problem?

Of course I had to call Kristina immediately upon getting back to my room to talk about the date and ask her to help figure out what had happened. Her immediate response was what kind of move did you make? HUH? Well, you got her to agree to go to your hotel for a drink. What did you say or do to try to get her up to your room? I let her know what a gentleman I was and that I could see how vulnerable Yuki was and couldn’t take advantage of that, to which she replied You idiot, she went out with you to get laid. God you are such a pussy when you try to be nice. Would you fucking stop it and be something close to the man you once were? She continued to tell me how Yuki had confided in her she just needed a man to plow her really good to help get over her ex, and Kristina assured her I was the perfect man. I had completely blown what would have been an easy night of angry sex.

The next night Kristina insisted on having dinner, and spent the entire time telling me that marriage had changed me, and not for the better. She explained that before I had met my ex, I was the type of guy that didn’t really care what people thought, had just the right amount of swagger without being a cocky prick, hit on any woman that looked decent given the amount of alcohol consumed at the time, made everyone around me laugh, and generally enjoyed life. She told me what had attracted her to me was that I was this average Joe looking guy who knew what to say, how to say it, seemed perfectly safe but at the same time, had an edge that made him someone you wanted to know. In her eyes, I wasn’t a player but I had plenty of game back in the day without really trying. Somewhere along the way, that guy was replaced with someone who was very concerned about what others thought, lacked confidence in his appearance and personality, and tried too hard to be politically correct. She told me that if I were to have any luck with dating, I would have to find the old me soon, otherwise I’d end up with a clone of my ex, someone who, in her eloquent words would keep your dick in a jar above the sink for use only on special occasions.

Looking back, my advice to men is that eventually you have to be the guy and make a move. In most cases, it's not going to be on the first date, though you have to pay attention and take any openings that are provided. If you don't make the move when she wants you to, you end up either getting dumped or trapped in the friend zone which is probably worse. It would take me awhile to figure this out.

Meet The Internet

November 2007 - San Francisco

As I knew Kristina would never set me up again, I decided to try a new route, the Internet. Being an old tech geek, I knew my way around the web, but really hadn’t embraced the whole social networking thing. My first venture was on MySpace. Quit laughing, it worked. I didn’t want my face out there, so set my pictures to be private and didn’t provide a lot of personal information. Within a week, I was talking with two women in the bay area. Yes, they were both in their 30s, and no, I didn’t get shot down by high school girls first.

The first woman I met was Anna, who was also going through a divorce. She explained that her husband had moved to Japan for work and to have some time apart during a rough patch in their marriage. They had seemed to work things out through phone calls and emails while he was there, and the prior Christmas she flew over to reunite with him…only to be told on Christmas Day that he wanted a divorce. We emailed back and forth and shared pictures, and I knew she had potential. She had a great sense of humor (could quote lines from Princess Bride), seemed very sweet, and was attractive in her pictures. We arranged to meet in Union Square, and I must say, her pictures didn’t do her justice. She was a knockout, and incredibly funny and sweet. We had a drink before dinner and during the meal exchanged witty banter for over an hour. I told myself that later that evening, I would figure out how to make a move, because I wasn’t going to be shot down a second time for not trying anything. At the same time, I wasn’t looking for a one night stand and didn’t want to seem overly aggressive. In other words, I had no idea what I was going to do.

After dinner, she told me that she had left her car near her office, which was a mile away. Since it was getting late, I insisted on walking her back which gave us more time to talk. In return, she offered to drive me to my hotel, which I took her up on. As we got closer, I asked if she wanted to come in and have a nightcap in the lobby (which I decided would be quickly followed with a second drink in my room)…and she told me that while she thought I was funny and interesting, she couldn’t see us being more than friends. DAMN! 0 for 2. I hate dating. We did email each other for about six months before losing touch, and hope wherever she is, she’s found the right guy, because she’s quite the catch.

Since Anna didn’t work out, it was on to the other MySpace woman, Meg. She was my 2nd choice, mainly because she didn’t live in the city, but somewhere between SF and San Jose. She didn’t like to drive, so I had to take the train to meet her. I didn’t mind because I knew Kristina was happy to not have to entertain me every night, and because I thought it would do me good to at least try again after my first two failures. Since she wanted me to come down to meet her and I didn’t know the area, I let her recommend a location. She suggested we meet in a small town at an Indian restaurant, which didn’t sound