How to Crush Online Dating and Become a Boss



A Background Story to Dating Online

I was talking to a co-worker of mine. We’ll call him Dave. I was offshore on a rig and a lot of guys in this industry usually have been prior military service as I am. I’m prior U.S. Navy and I’ve seen a lot of families broken up or split up by divorce over the fact that their spouse is gone for large amounts of time and it creates a wall between the people, and eventually a breakdown in the relationship.

A relationship does need to be nurtured and this is a special type of situation. I’ll tell you how this relates to online dating. Dave was married, and he had gotten divorced with his first wife. It was for the reasons I just stated.

When Dave wanted to get back on to the dating scene, he was a bit older, his children were pretty much grown. The youngest was 17 at the time, and his children decided he needed to stop moping around and sulking. Any time he had some free time when he wasn’t spending with his kids, he just sat at home and never went out, or did anything. He wouldn’t have found anyone under those circumstances.

The Move to Searching Online

His children set him up a profile online, and initially, he only had one picture. He mentioned that it wasn’t a very good picture, and he started getting lots of feedback. Dave said that in the first month of looking through all the messages he had gotten, most of them were a waste of time and he ended up deleting those people’s messages. One thing was that he was very specific in his online dating profile so that if he got a response that violated one of the criteria from what he wrote in his profile, he immediately deleted them. He said he almost gave up and didn’t want to try again. He said it was irritating and he didn’t want to go out to the bars and clubs. And again he was older so that wasn’t his ideal type of crowd or situation and he had no desire to actually meet people or date in this way.

Dave tried online dating. If he had given up and quit initially, then he would never had met his wife currently of 10 years. He said it was a perfect fit for him. And in that same way, to be a boss, you have to sift through a lot of garbage before you actually find that diamond. It might take some time but, you shouldn’t be trying to get hitched because of desperation or because you just want a partner that bad. Take your time in online dating. I’m going to give you some tips to be a boss. And I’ll use criteria similar to what he used for his online dating profile. Then I’ll give you some specific actionable steps you can take so that you don’t get tricked.


What Makes Online Dating Effective?

Lots of people are not very fond of online dating because I hear them mostly say well, a person could have a fake picture up there or they could be lying, or they don’t look like their picture. They are not what their profile said. But how often does it match up when you meet them in person either? It’s pretty much the same, and everyone tries to rush past the one thing it takes to build a quality relationship, and that is time. Time to get to know one another. Time to see each other’s mannerisms, how they treat you, how they treat their children if they have any, and other important things you can only learn with time.

Maybe you found out they had a girlfriend or children and in actuality, although this does happen, it is a very low percentage of times that it does happen and I’m going to get right into the tips to make this less strenuous. I’m going to show you how you can get around things like that and tell if they are being honest and some other places you can check to make sure their story pans out.

Frequently Asked Questions people often ask about online dating

  1. What if a person has multiple women in different areas? When my wife and I first started dating, I had multiple suitors, and multiple options I wanted to pursue. That is normal. But once you make it through some of these stages and steps I mention in this article, you should as we did, delete your profiles from those meeting sites, and discuss becoming monogamous with each other. One note here: If the person does not stay in your area, long distance relationships (LDR’s) don’t work and I wouldn’t recommend trying it. I’ve done it, I’ve researched it, and it can work, but the percentage of people who make it work is less than 1%. If you want to go for that one percent change then be my guest. There are multiple reasons LDR’s don’t work but that’s another topic for another day.
  2. What if they have fake pictures and aren’t honest? People aren’t honest these days anyway. This doesn’t apply to all of course, but when we meet face to face, how often are we manipulated, tricked, or lied to? This seems common so this shouldn’t be a barrier to entry of meeting people online. They could be dishonest just as easily online as if they were in person. To make sure you aren’t duped, here’s what I recommend. Search their name on multiple social media channels. This will reveal their associations, people they hang out with, their thoughts and ideas, and whether they are lying about how they currently look. For instance, if they say they don’t have a girlfriend or any kids, you can search their Facebook, Twitter, Instagram, etc., and people will usually have pictures of their family or significant other if they are currently hitched. So you can call BS if you search their name and find something different from what they’re telling you. You should snoop before you get involved deeply. As I always teach, any relationship you enter in is taking a chance, and isn’t guaranteed to work. That’s in any case.
  3. How do I avoid wasting time with online dating? Be specific in criteria you require or standards and boundaries you set. Then, when you are searching, you can automatically eliminate people whose profiles don’t meet your standards or people who aren’t consistent across their channels. Remember to look at what they do more than what they say. You should be selective. You shouldn’t entertain any and every body who gives you a shout out. Stick to a set of acceptance criteria you are looking for.

And, with all this, be patient. These things take time. Getting to know someone takes time. Don’t rush it or you’ll constantly be disappointed. If you have a problem falling too fast, get some self-discipline and just wait.


3 Tips for Qualifications

  • Eventually a healthy sex life must be a part of the equation
  • Don’t try to change the person accept them as they are
  • Be on an even playing field having been established on the same level or better financially and in the areas of stability and career

4 stages to the final transition to a relationship

  • Chatting within the site/app
  • Transition to emailing
  • Transition to talking on the phone (key word is talking)
  • Transition to meeting in person


The Timeframe Guideline: Transitioning from Online to meeting in Person

Once you transition to meeting in person, follow the steps in my other article (3 stages of getting to know someone)

  • The Exploratory Stage
  • The Declaration Stage
  • The Groundwork Stage

For a refresher on these stages and the guidelines to follow, read The 3 Stages of Getting to Know Someone.

This process should take approximately 4 months from the first setup of the online profile to going out on 5 dates. (Reference in the 3 stages of getting to know someone article.)

  • Sites can be free (should be if you’re low on money)
  • Sites can be paid (I would recommend trying the free sites out first before trying out the paid platforms)


Free Sites include (most of these sites have a paid option also but you can set up a profile and chat for free)


Paid sites include:

  • match, eharmony, zoosk

Sites to Avoid

  • Tinder, Plenty of Fish

All I’ll say about these two are that they are strictly related to booty calls and friends with benefits situationships. If you’re looking for a solid relationship or quality candidate, you won’t find them on Tinder and Plenty of Fish. You will find guys who will only aim to sleep with you. These sites are geared more towards the “Netflix and Chill” type situations.

I didn’t mention Facebook although it is the number one social media platform out right now. But it isn’t geared specifically towards meeting people for relationships or hookups exclusively like these other sites are. The same rules, principles and guidelines from this article apply there as well.

I’ve tried all of these sites except for eHarmony, Tinder, POF, and Meetup, but I heard Meetup is pretty good as well. The rest of them work pretty well. I talk about meeting potential candidates online in my book in chapter 10 The Round Table. If I didn’t mention it before I met my wife online on, and we are married with 3 kids and have been together 9 years as of this writing. Online dating is certainly viable and readily available these days with most everything moving to an online platform. So why not dating? It’s where most people are these days anyway.

Once you transition to meeting them, if you still like them (because you must be attracted to them) then start checking out all their social media to look at their associations and things they post (Instagram, Facebook, Twitter, and LinkedIn if they have any of these sites).

This process is taking care of the element we rarely see these days, which is getting to know each other. Then I would tack on an extra 2 months if you have kids, I recommend never to let anyone meet the kids until at least the 6th month. By that point, true colors will start to show. True intentions, and folks who have put up a facade will drop out. This is what I call the 6-month vetting process.

Those last 2 months are to observe and make a final decision whether you want to waste more time, or continue to grow the relationship. The last 2 months are also to propose a date on meeting the kids after that 6 month mark.

Wow, this is timely. As I’m writing this article, I’m in the mall in the food court, with my computer open and my headphones connected to my phone. Just now a tweet comes in and it mentions a site about finding out if your mate is cheating. I don’t ever include little links like this, but since we are talking about online dating, it was specifically applicable. So here it is. The post said they found out their ex cheated with multiple online dates so, yeah I think this is applicable. I went to the site, and all you have to enter is the suspect’s email, your name and your email. And it has a red button to search and it says its $5.99. You could try it. It might be what you’re searching for.

On another note, if you have the inclination to use such a service, don’t you think there is a deeper issue there? Maybe trust? Maybe something else? Don’t even waste your time with the search. Do one of two things. Either have a discussion with your guy, or just leave since you can’t trust him.


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