These days when we turn on Soundcloud, Spotify, or the radio, we hear lyrics that sell fantasies of epic love – executive men who hand you their credit card or a stack of cash, give you a quick peck and tell you to take the day to de-stress however you need…on him (pun fully intended)! Then there are songs that go something like, “I want to be with you for more than just sex, and I want you to have all my babies and we’ll get through all the BS that life throws our way.” Basically a Disney movie set to a dope beat.

Ladies, raise your hand if you’ve had a sip of the kool-aid and your relationship fantasies are about as vivid as the porn your loser ex boyfriend is probably watching right now.

C’mon, admit it. I’ve done it too.

Many women who’ve always wanted to date or marry a successful man see the greener grass on the other side, but what they don’t realize is that the truth Drake spits is real:

“We live in a generation of not being in love and not being together, but we sure make it feel like we’re together…”

or how about…

“You got a different vision
You wanna walk around naked in the kitchen
Without runnin’ into one of my n****s
That’s not the way we livin’”

There are a number of challenges that come along with loving executive men and sometimes those challenges can negatively impact the euphoric feeling of “being in love” or getting him to commit to you. For those of you who are standing on the other side of the fence without a successful man, looking at my grass and thinking my grass is green, and for those of you who are standing on my side of the fence wondering how you can actually make your grass green, the first thing you need to do is understand what some of these challenges are.

Lucky for you, I’ve put together a list that does just that! During the rest of this month, I’ll be sharing more in depth posts that tell you how to overcome some of the most common challenges in the list below. Read on sweetie…

1) Executive men don’t know how to have fun

Because he has spent every waking hour working or thinking about work for the last 699460456 years, he doesn’t leave any brain bandwidth to spend on thinking about how to relax or have a good time. This can quickly shorten the “honeymoon phase” and make your relationship hit a plateau that is covered in crazy glue. Next week, I’ll share a story about a recent dinner I had with a CEO, his wife and a former executive-boyfriend of mine. This was the exact topic of dinner conversation. Hopefully, you’ll gain some insight about how to unglue you and your executive from that plateau without being called a gold digger. Hint: Wait for him to complain about being bored.

2) He won’t talk shop with me

He will spend hours on his phone, ignoring you, responding to emails or taking calls. Then he’ll sigh and rub his head in a frustrated manner. Hell, he’ll even be short with you for no damn good reason. Reasons, which are very likely caused by work, but he won’t spill the beans about exactly what’s going on. Meanwhile, all you want to do is a) understand what’s causing him his grey hair and b) to maybe offer a bit of advice. There are ways to find out what’s bothering him without snooping through his phone while he’s in the shower.

3) He talks to me like I’m a client or an employee

In the beginning, these men talk to you like you’re a client, being careful not to offend or correct you. It’s cute at first, but you can’t wait until he drops the act and is just REAL with you. It’s not long before nothing you say is right and he’s giving you orders as if you’re an employee. I’ll tell you exactly how I successfully worked through this issue in my most recent executive relationship and you can too.

4) Executive men are constantly crunching numbers

It doesn’t matter how small or insignificant a purchase is, he won’t swipe his credit card or sign on the dotted line unless he has convinced himself that the numbers make a convincing case to make the purchase. If you’re a deal hunter like I am, you might find this behavior endearing. The ability to evaluate price against value when making a purchase can be useful when making milestone or big-ticket purchases to help justify the large expense and make financial planning easier. On the regular, however, this OCD-esque behavior can be a major lady boner killer due to challenge number 4.

5) He won’t do anything impulsive

Ever wanted to show up to the airport and take the cheapest flight you could get to a random place? Yeah, he very likely won’t do that. I know none of mine ever did and I can’t wait to share with you some of the excuses I’ve heard over the years. I agree that this is a bit of an extreme example, but the same can be said for a 2-3 day road trip, or making an impulse buy, or jumping out of a plane with a parachute. Everything has to be planned. He needs notice and it HAS TO BE in his calendar.

6) He has never taken me out on a proper date

He’s swamped. He doesn’t have time. It’s too much work planning a date. It doesn’t matter where he takes you because he never gets it right anyway. Or maybe, he just doesn’t have the amount of dating experience it takes for a man to know how to take a woman out on a proper date. I’ve heard all of the excuses and there are only 2 things that’ll stop the excuse-parade: lingerie to get his attention and a carefully executed conversation. You can tell him to take you out on a proper date but it’s like speaking French to him (assuming he doesn’t speak it of course). He has no idea what a proper date is. So what do you do? The answer is not glamorous so it will surprise you.

7) He doesn’t play by the same rules

Executive men want an intelligent, talented, well read, super model. She has to cook better than a red seal chef and have an established career outside of the restaurant industry. Oh, and, he wants her to be willing to give up that career to move to a different country, state or province when a new opportunity arises for him to trot the globe. And also, she should be over the moon about absolutely destroying her body in order to have his babies. Babies, which he won’t be able to help raise because he’s to busy being an executive. Soooo, that means she has to drop her well established career. And lastly, she has to sign a prenup to prove that she isn’t a gold digger because his assets are greater than hers. But are they? ARE THEY REALLY???

8) Executives can make friends and family feel less than

There’s an art to teaching humility. You’ll have to learn to teach this quality quickly if you hope to keep him around. Mostly executives think and therefore speak like they’re always right. Their filter is a bit skewed because in the workplace, where they spend most of their time, they are right. This is why these men come off as know-it-alls and when they are right outside of work, they rub it in. That’s IF they show up to family and friends’ events and stay for the duration.

9) He’s usually zoned out

You got him to take you out on a date, but don’t celebrate yet. He might not show up all the way. If we had to rank all of the things with which you had to compete for his attention, his own monkey brain would very likely top the list. Other women, if at all, would be at the very bottom. Executives’ long list of things to do are their own special kind of cancer. They spin like a hamster wheel in their heads until there’s nothing more than a zombie left on the outside. So, what can you do short of punching him in the family jewels that will get him to give you the time of day when he’s giving you the time of day?

10) The sex with executive men sucks and not in a good way

Hockey players start skating at age 4. Baseball players start throwing a ball around when they’re 5. Basketball players start shooting three pointers when they’re 7. Executives start having sex when they’re….29? 32? Older? Do you see where I’m going with this…?

The trick to winning an executive man’s heart is to anticipate these challenges and not let them get under your skin. Hopefully, you won’t experience all of these challenges with one guy, but these are some of the common ones that come up after the honeymoon phase ends. Often, people get worked up and end a relationship because they don’t see a mutually beneficial solution to a problem. Butttt this won’t be you because before we ring in the new year I’ll tell you exactly how to work through these challenges successfully at any stage of your relationship with an executive man. Get into the Candy Jar so you don’t miss out on this series of posts!




  1. Anissa January 1, 2018 at 8:47 pm

    This is interesting! Unlike any other blog I’ve read before. Definitely helpfull tips for those who are on that situation! Great post!

  2. Wiola January 1, 2018 at 7:53 pm

    Haha, I really enjoyed reading this article. The moral is – do not date the executive man cause you simply won’t be happy…. I wouldn’t like my man to talk to my just like to the client etc. And I love guys who are spontanious. Fortunately, my husband is not an executive man…. let is stay this way forever, please.

    1. M January 1, 2018 at 8:22 pm

      Glad you enjoyed it! I’d say the moral is to read about each of the challenges and learn to overcome them. Executive men need to be loved too 🙂

  3. Juli January 1, 2018 at 7:17 pm

    These are some well put out thoughts about these men, but I beg to differ that they all come with these baggages

    1. M January 1, 2018 at 8:20 pm

      No, not all men have these issues, but these are the most common ones that come up when in a relationship with executive men 🙂

  4. aliece January 1, 2018 at 6:31 pm

    great post


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