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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.

10 Cheap Dates In and Around New York City (Part 1)

Robert Manni - Friday, December 08, 2017

No matter where you live, being single and in the market for love in New York City can be expensive. And if you live in Manhattan, the stakes are raised. There are thousands of single people and cocktail and coffee bars in New York, and you can run up some serious debt once you get a taste for the amazing women and all the cool places to go in this town. So you’ve got to use your noodle if you want to be able to save some actual cash for that real relationship you may be gunning for. Dating and relationships cost money, and if you’re in the stage of life where dating is a sport, it can become a very expensive hobby or pastime. A night out with dinner and drinks can easily run up a bill over a few hundred, not even factoring in your Uber, taxi, or the dreaded mass transit ride home. And even if you are only out for drinks, at $20 a pop, two rounds of hipster cocktails and some apps, plus tax and tip can cost a C-note. With wages still stuck at 90’s levels, dating is very costly indeed. Dating should not cost an arm or a leg, and you work hard for the right to meet a few potential new partners a week while in your prime single years. This is when you want to have fun without having to think about what you are ordering and every penny you are spending. That’s a drag.

So what’s a Guy’s Guy to do? It’s easy to meet women in this city and even easier to score dates online or through all those apps. But how can you enjoy the company of a pretty lady or two without breaking the bank? Well, amigo, every romance has to start with the proverbial first date, so you need alternatives to drinks at the latest mixologist lounge. Like free bar finger food, you Guy’s Guy will offer up timeless starters for first dates that will help you get to know and make a good first impression without the stress of emptying your wallet or crypto-currency account. So, I have picked out ideas to help you get to know someone new without busting your budget. I’m also assuming that the Guy’s Guys reading this will at man up and offer to pay for a first date with a young lady who has caught their eye. I’m going to start with five options this week, hoping you give at least one of them a try before I toss out another five your way next time.

Drum roll please… 

1. The High Line – Way, way back, what is now known as the High Line used to be a railroad that shipped goods between the Meatpacking District and the rail yards near the docks adjacent to West 34th Street. The rails stayed put after the trading and shipping along the lines stopped years ago. During the late nineties, a group of smart New Yorkers, including David Bowie, decided it was time to clear away the overgrowth and turn the High Line into an above ground pedestrian walkway. It was a brilliant vision, and soon the money flowed in so that the work could begin. The transformation was handled in chunks as sections beginning around West Street and worked north until the project reached completion this year. And what a job they did. The High Line is a gorgeous path that winds its way a level above the far west side of the city through various condo projects and the Hudson Yards. It takes about thirty minutes to walk and at a cost of zero it’s hard to beat. If you want to break for refreshments there’s a brewery and a number of coffee houses and cafes along the way. The High Line is a fantastic first date location that won’t cost you a dime if you don’t feel like stopping for a brew or a cup of Joe.  

2. Central Park – Okay, so this isn’t new like the High Line, but having traveled the world, I can’t think of a better place to run, walk, enjoy gardens, fountains or flowers, play tennis or softball, throw a Frisbee, walk a dog, take a boat ride, go bird watching, hike a trail, see a puppet show, or take in a zoo than glorious Central Park. And, almost everything you do in the park is free. The park spans from Fifth Avenue on the East Side to Eighth Avenue on the West Side and from 59th Street to 110th. It’s a big, vast, and it gets better and better every year. If you are looking for a solid pick for a first date or meet up, consider all the options the park provides. 

3. Koreatown – The 32nd Street strip predominately between Fifth and Avenue of the Americas in Midtown is home to what’s often referred to as K-Town. The restaurants on the street level serve delicious, savory, healthy hot meals at great prices. On the higher levels you’ll find bars and karaoke clubs where you can drink and sing with people from all over the world. And the women are very pretty. There are lots and lots of places to choose for great food and drink and K-town is relatively inexpensive. 

4. Battery Park City – Although New Yorkers usually think of this downtown West Side strip of land as a boring, residential oasis, it’s actually a very nice area to walk along the water and take in the sights, or grab a bite or a brew. You can to learn how to sail, sit at one of the many outdoor cafes, or stroll further downtown through the sparkling new Oculus transportation hub and Brookfield Place with its many shops and restaurants. For a cheap first date it’s hard to beat a walk along the ever-improving waterfront or taking a Water Taxi to another stop along the coastline. And when there is a lot of gorgeous nature to take in with your eyes, it becomes easier to manage how much green is coming out of your wallet. 

5. Harlem – After spending a year looking for a place to live, seven years ago I moved from Midtown to Southwest Harlem. And I have never looked back. It’s a wonderful place to live. Don’t call it SoHa, though. Eighth Avenue turns into Frederick Douglass Boulevard after the circle on 110th Street. FDB, as it is known, functions as an entry point to Harlem for a surprising number of New Yorkers who have no idea what to expect or where to go when they head uptown for the first time. One of the great things about Harlem is that most of the buildings, even the newer condos, top off at around twelve floors. This creates a significantly more open purview than Midtown and the streets and avenues below in Manhattan. Although Harlem is filled with lots of history and art, if you are coming here for a first date, I suggest you begin with a walk along FDB north between 110th and 125th or up one of the blocks nearby. This gives you easy access to more options while you’re on a first date and probably learning your way around the hood. There are a number of bars and restaurants along FDB on this strip that won’t empty your budget. Harlem is not cheap, but it is not nearly as expensive as Midtown. You can also take a walk along the Harlem Meer near 110th Street in Central Park or check out the Lasker Rink for a swim or a skate depending on the time of year.

You have five very different options to consider for a cheap first date, and we’re only halfway done. Next time I’ll offer up five more hot and cool locales for you. After that, amigo, you’re on your own. I’ll hold off on naming our Guy’s Guy of the Week until part two of this post. So, now you’ve got a week until I reveal the next five options, so get out there give one or two places a try, and let me know what you think.


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