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On Life, Love and the Pursuit of Happiness

The Guy's Guy's Guide to the 4 Types of Daters You'll Meet Online

Robert Manni - Friday, May 25, 2018


Once upon a time, a guy entered a restaurant. He noticed a pretty lady sitting at the bar. Wanting to meet her, he sauntered over, smiled and introduced himself. “Hi, my name is Lou. Can I buy you a drink?”

She looked him over and smiled back. It doesn’t matter what happened at this point, because the possibilities were endless and many of us lived that scene back in the day. And every now and then something like this still happens. But not so much anymore.

Dating, like everything else, has gotten complicated. Real complicated. Dating used to be a fun sport. Now, too often it’s a combat sport.  And it’s really a jungle out there. So most singles have retreated to the comfy confines of their bedrooms to engage digitally. The first step is downloading the usual dating apps and signing up on dating websites in the hope of finding a compatible, but probably equally confused partner.

When you approach dating online, you’ll need to be sharp and have a strategy to avoid the emotional landmines that lay ahead. And if you pay attention and learn the game, you’ll soon know how to save lots of time and heartache by qualifying your prospects. But if you’re dating online and haven’t figured this out by now, you’ve come to the right place. Your Guy’s Guy is here to help you separate the wheat from the chafe and make the most of your time and efforts while swiping left or right. I went on so many online dates that I learned the hard way how to qualify prospects before investing my time, money, and psychic energy in someone I had up to that first face-to-face encounter only met online. So, here is my GUYS’ GUY’S GUIDE TO DATERS YOU’LL MEET ONLINE.

Drum roll please…

1. The new kids on the block – At one time or another we’ve all been the new kid in the game. We’ve all wasted a few online prospects’ time before they figured out we had not yet figured out how the online game is played. This happens when you begin the process by plinking on your keyboard in your tightey-whiteys in the dark of your bedroom to meeting that straight up stone cold fox in person. She expects your A-game. But it takes a time and finesse to sharpen our online skill set, so let’s not be too hard on the newbies we encounter online. Qualify and if necessary, move on. We’re all rookies in the beginning and that means we probably have been more focused on the shiny object dangling on our phone or computer screen instead of determining who you are, what you want, and what you have to offer a partner. It seems that most online daters miss this first step.

Meeting someone who has never dated online is often a waste of time. In my experience, I met a number of very attractive, intelligent, and pretty cool ladies who had never been on an online date. Rookies tend to have a lot of questions, but few answers. They are often very recently single, separated or divorced. They are dabbling, curious and attentive as they inquire about you. They nod their head as they listen attentively and subconsciously compare you to their last boyfriend or ex-husband.  After a while, they may bring up their two daughters or the fact that their ex–whatever still lives with them or is in constant contact even though he is a douche. So you glance at your watch and realize that this was a waste of your time. She is a newbie who does not know what to expect or what she wants from online dating. It’s an eye-opening experience for her. And that’s perfectly understandable. But, shame on you. Her pretty photos sucked you in without your taking the time to qualify her situation before agreeing to meet. So, you lose and she now knows a little bit more about online dating. Wasn’t that fun? Maybe you thought since she’d been married she was generous in the sack and ready for some sheet rumbling with a new guy. You were being selfish and lazy. I know. I’ve been there, amigo.

But that’s not it. She simply was curious about online dating and you were a vessel to fill in some of the blanks before she moves on and dates another half dozen guys before she has a handle on the online dating game, what she wants out of it, and what she expects in a partner.

My advice is in most situations, try not to be the first dude a newbie dates online. Qualify this prior to meeting up unless there is something special there that really sparks your curiosity. Otherwise pass.

Notice I said, in most situations. When it comes to online dating you might craft your rules to live by, but rules are ultimately meant to be broken. There are always exceptions. Case in point—my wife had been recently separated when she winked at me online. I liked what I saw and read about her. Her personality was refreshing so I took a chance and met her without even a phone call. This was my way of breaking my own rules, two of them. I always wanted a phone call first and I did not want to date recently-separated women. But, like I said; rules are made to be broken. So we met and really enjoyed our date. In fact, we have been together ever since. So, there are exceptions, but before dating an online newbie, use your head. That means the one on top of your shoulders.

2. The jugglers – Also known as players, these attractive men and women treat dating like the game it is. And they know how to play to win. Theses cool cats double- and triple-book their life in the big city and always have a backup plan. They’re usually good-looking (worth mentioning again), well-dressed and coiffed, and usually have a good job. When you meet up, they will eyeball you quickly before judging and labeling you. You might become dinner date material for you business connections, bedroom worthy, a rich guy, or creative type who stimulates their curiosity. It doesn’t matter what category you fall into or how you are labeled because most of all you are a disposable social connection that may or may not fit into the complicated puzzle of their unnecessarily over-complicated lives.

Don’t take it personally. These players move like sharks through the dating pool, devouring those who find their way in their path before they move on. You may think you’re making it with them at first, but the slightest infraction will get you voted off the island.

Now don’t get me wrong. Players are fun and they can be sexy, but remember who you are dealing with and don’t take yourself too seriously. These swingles move very fast and unless you can keep up with their demands and lifestyle, you’ll be jettisoned. And that’s okay as long as you can live with the reality of dating a player who may temporarily position you on top of their love totem pole after you’ve done whatever they expect you to do to get there. And that will probably be expensive, so buyer beware.

3. The lonely – Whether online or offline, there are a lot of lonely people in this world, especially in big cities where the tenderhearted can get overlooked by the more flashy players. You know the type.

She moved to New York from Missouri because she is smart and feisty and wanted that Mary Tyler Moore moment when she throws her hat up in the air. And despite the crime and the grime and the expenses, she is in love with the city. And that makes her vulnerable. She’s a great gal with decent job and a nice, clean apartment with big fluffy towels in her bathroom. But she’s never really gotten accustomed to the often-heartless behavior of urban males who have ghosted, bird-seeded or orbited her. She’s online because she wants to meet a guy and that’s what everyone is doing. She crafts a sincere profile and dutifully checks her emails every night hoping that cute guy she wrote to online will be the real deal. She expects men to behave like gentlemen online. But often, they don’t.

She deserves a man who will step up and date her like her dad wooed her mom. That might not happen. But, welcome to New York, anyway!

My advice. Treat this lady with care. If you meet her and don’t feel the vibe, pick up the tab and move on. Don’t seduce her and disappear because she is vulnerable. If the attraction wanes after a date or two, consider the possibilities of a friendship, unless she thinks you’re an asshole. Regardless, be kind and don’t waste her time or your time just to get laid. Okay?

4. The realists – These are the men and women who put up with all that shit in their mid-level jobs as an expected step in their life’s journey. They want some fun and excitement and hope to meet someone normal online they can date for a while and maybe build a relationship with. Is that so unreasonable? Of course not. This group represents the pig in the python for online daters—savvy millennial, GenY, and X’ers who are doing their best to make their mark in this dysfunctional world the older generation left them with. Thanks a lot, boomers!

These hard-working people are the backbone of society. They deserve a little fun and a good partner. The good news is that most people dating online now, whether make up this group. So if you are a decent person with a sense of humor and a job, you can probably have a great time meeting people online. Online dating is no longer the exception. It’s the norm and you can meet a lot of cool men and women there if you keep your antenna extended and learn how to protect your time, money, and your feelings before falling to one of the many online dating sinkholes. I hope this helps.

This week’s GUY’S GUY of the WEEK is my wife. She spent one weekend during a free trial for an online dating site and dated only one guy who became her husband. That’s impressive. But, so is she. After all, she married a Guy’s Guy.

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