Diving In: Over-40 Dating for Executives Notes on dating today and how to navigate the minefield of social media, apps, style, and more.

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Okay. You’ve done it. You’ve accomplished nearly everything that you want in your professional life, and your social life is pretty great too. Now, you finally feel like you’re ready to start dating again, maybe even get married and perhaps start a family. But it’s been years since you’ve last dated and you’re feeling anxious about the whole thing.

How do you get back into the game? What has changed? What about all of this new social media, and how can you use that to your advantage? What pitfalls are there to look out for?

And how do you deal with body image issues if you’re not feeling good about yourself? 

Another question is, what is the best way to dress for a husky executive? Don’t forget to check out our article on this subject this month. 

But also, what about all of these new dating apps? Is it a good idea? Which are the best ones? And what advantages and disadvantages are there to them? 

Let’s examine these common questions and unpack useful advice to get started.

Honestly, dating is a vast and very, very important topic. Think about it for a moment. Whom you choose to date and marry can significantly affect you for better or for worse for the rest of your life! And if you want to have kids with your spouse-to-be, your choices now could impact generations of experiences to come – it’s your lineage!

But don’t feel pressured or fear it! Finding the right partner and creating a beautiful family will be one of the most rewarding and satisfying things you may ever accomplish. Change FEAR to mean “Feeling Excited And Ready”! 

Just realize that the decisions you make now are critical and don’t settle. You deserve to have the best that life has to offer. 

Let’s jump into the topic, shall we? 

First, let’s get the pitfalls of dating out of the way.

2. Pitfalls of Dating Today

Dating apps are everywhere nowadays. Some of them take a lot of time, money, and energy to use. There are some apps like eHarmony that ask all kinds of questions to connect you with someone whom you will have things in common with but the reality is that the app is only as good as the information that is put in. And who can be objective about themselves? Hardly anyone! What you may find is that people become who they would like to be, rather than who they are. 

But that’s normal and human. That’s one pitfall, but there are more. 

Nowadays, your personal information online is getting more and more difficult to keep private. This means people can now dig up information on you that you would swear only a highly paid private investigator could have found out! How do I know? Because it happened to me! 

Privacy is why it is always best to be as honest as you can; however, that doesn’t mean that you need to open every can of worms – especially in the beginning. 

Here’s another problem. You may find a beautiful person online, and everything their profile says seems perfect but then, you meet them in person and the chemistry isn’t there at all. Or they may not have it for you. 

Prepare yourself for that to happen. Look at it as par for the course – and that it may very well happen. But that’s okay! The more you date, the better you’ll hone your dating skills for that one, perfect person for you. 

Now, let’s talk about your body image.

3. Body Image Issues

The thing that most guys don’t realize is that a high-quality person will not judge you by the size of your gut, but by the size of your real character. What’s most important is that you have a positive self-image regardless.

That doesn’t mean that you should abandon improving your physical fitness and diet. It just means that us guys usually make way too big of a deal about it. 

You see, when you let your looks bother you, that’s what bothers people the most. It’s a sign of insecurity and that is a huge turn-off. 

Don’t ever let a person know that you are self-conscious about your body if you are. You will appear weak. You are not weak! You are a powerhouse. The way to improve your body image is to truly not be self-conscious about your body!

If your weight is an issue, do something about it. Diets don’t work because it implies something temporary. Do a lifestyle change that allows you to lose weight comfortably and sustainably, and then stop obsessing.

Life is too short. Look up intermittent fasting and learn how to burn fat efficiently and without hunger pain. 

If you’re still having issues with being self-conscious about your body, realize that who you are is much, much more critical to a quality person.

Make time for yourself to take better care of your body. Eat as much organic and whole foods as you can, stay away from junk food (for the most part), get plenty of sleep, and join a gym or seek outdoor activities. Whatever you do, choose to feel good about yourself now. Don’t wait!

4. How to Dress

There are lots of great sources out there that explain how to dress for husky guys. The basic principle is to dress in a way that accentuates your height and gets the eyes to look at you vertically. This is why suits that are of the same color and fabric for both the jacket and the pants look great on shorter, husky guys. Another thing you can do is to wear a fashionable hat to make you look a little taller. 

You don’t want to wear anything that is either too tight or too loose. The right fit is why it’s a given that you should use a good tailor. But if you’re going to err, err on the side of too loose. 

Look up “Real Men Real Style” (RMRS) on YouTube to get excellent tips. Also, Men’s Wearhouse is an excellent store for bigger guys. 

5. How to Date Successfully

Here are six do’s and don’ts for successful dating:

Tip #1: Don’t Be Creepy!

No matter how much money you make, nor how great you look in your Armani suit, if you act creepy towards a person in any way, shape, or form, it’s over. What’s creepy? It depends on the person! Let’s list most of them:

  1. Stalking them in any way, shape, or form. That includes online! 
  2. Being pushy.
  3. Coming on to them too soon and not knowing how to read the signs. 
  4. Contacting them too much through text, phone, voice mail, or email. 
  5. Saying inappropriate things too soon. What’s inappropriate? Whatever they think it is! 
  6. Sending presents and gifts too soon. Again, “too soon” is subjective. Use your intuition. 
  7. Getting upset/angry about anything and anyone too soon or ever, but you have to stand up for yourself.
  8. Getting upset if they don’t contact you “soon enough.” It may be a test. You have to be patient. 

Tip #2: Find Out How They Treat Others

The quicker and sooner you can find out the following essential things, the better. Your time is precious. And the more you value your time, the more the right person will respect you. At first, don’t take their word for everything. Assume that they are going to stretch the truth to some extent on many things until otherwise proven. Here is a list of things to observe and ask:

  1. Carefully ask about parents, siblings, friends, and even enemies. How they answer will give you clues as to what they are. 
  2. How do they treat people? Notice how they treat a waitress or the Uber driver. Are they respectful? These are all signs of who they are. But remember, they could be putting on an act too.
  3. Do they clam up around other people? Why? Or are they a social butterfly and too friendly with everyone for your taste? Take note.

Tip #3: Look for Red Flags

 Here is a list of red flags. If even one of them appears, get out. 

  • They’re cynical about things. Most everyone is on their best behavior while dating. If they’re already too negative, there’s much more under that iceberg.
  • They don’t like mom or dad. There are exceptions to this, but if you want to have kids, do you want them spending any time with someone whom your partner doesn’t like? That will be your child’s grandparents! Sorry, but you deserve the best. Don’t ever settle.
  • They treat their children poorly
  • You catch them in a lie. 
  • They’re financially unstable. 

Tip #4: Don’t Be a Beta Male!

It’s surprising how many guys who are total alpha males turn into total beta males whenever a person of interest appears. Don’t be that guy! It’s a self-confidence issue and also a deserving issue. It’s a complete turn-off to a person, acting like a beta male will get you friend-zoned quicker than it will take me to finish this sentence. 

You have to learn how to take your alpha-maleness from the boardroom to the bedroom – from your work to your personal life. 

Believe in yourself, raise your self-esteem, increase your self-confidence. There are lots of ways to do this. But one of the best ways is through trial and error. Get out there and just do it. Date lots of people and your confidence will increase more and more. Embrace failure! Failure is the price you pay for success. You already know this. Just make sure to apply this knowledge to your dating/personal life too. 

Tip #5: Expect Them to Test You!

People don’t even realize that they do this. They will deny it! Why? Because it’s in their makeup. It’s in their DNA. Sometimes, they don’t even consciously realize it. It’s in their subconscious mind to test you.

It’s a survival thing that part of their reptile brain is looking for the best suitor. Rather than get upset about it, accept it and expect it. It’s also a good thing because it will help you to be a better man. Here are some of the tests they may put you through:

  1. The Integrity Test: People have the incredible ability to store memories. You will be tested to see if they can catch you in a lie. Expect it.
  2. The Past Relationship Test: They may ask you about your past partners. Do your best not to answer it! You can answer that question much later in the relationship, but in the beginning, don’t. If you say bad things about your ex, they will more than likely take your ex’s side! If you say good things, they will want to know why you broke up or prod you to say something terrible. Say something like, “I would prefer not to discuss it because I don’t want the past to interfere with this wonderful, present moment here with you.” They will probably melt and then later, call their friends and tell them your exact words. 
  3. The Temperament Test: They may purposely not call you to see how you react. Or, they’ll be a little late to know what you say. Or, they’ll talk about their past romances to see how jealous you may be. Don’t fall for it! They may not even consciously realize that they’re testing you – but they are. Be cool as a cucumber no matter what, and you’ll be fine!

Tip #6: Show Personality!

Who doesn’t love a Husky Executive with a Husky personality? People love to laugh. Who doesn’t love a humorous guy? But… what if you’re not? 

The truth is, you don’t have to be Jim Carrey to attract the person of your dreams. You just have to be yourself. And you want to know something? When you’re your true, authentic, easy-going self, you’re going to be light-hearted, in a good mood, and fun. Trust me, everyone is. It’s just a matter of connecting to that part of you and letting it flow. 

A little bit of humor can go a long way. It’s a lot more art than science. 

Just be yourself and be open to joking about things. Don’t take life too seriously. You’ll never get out of it alive!

6. Dating Apps

One of the most comprehensive dating apps is eHarmony. It is known for being a more conservative type of app where traditional relationships, like marriage, are the primary focus. They pride themselves on being one of the most comprehensive dating apps because they require everyone to answer many, many questions. That can be both a good thing or bad. It’s time-consuming.

Another top-rated app is Match. It’s prevalent among professionals and less restrictive. 

Then there are the others like Tinder, Plenty of Fish, OkCupid, Elite Singles, and others. Elite Singles may be one of the better sites because the focus there is on matching professionals.

In summary, dating over 40 is different from dating in say, your 20s. You’ve got your act together now more than ever, so take that part of you, that alpha-male mentality that helped you become successful in business and apply that to your personal life. 

Finding the right person to share your time is extremely important and you deserve the best. Don’t ever let your body image stop you from approaching even the most beautiful person you’ve ever seen. You’d be surprised at how many outstanding, smart, fascinating people are out there for you to date. 

And remember, don’t be creepy! Look for red flags. Once you see even one red flag, consider moving on. You don’t have time to waste on the wrong person. The right person is going to be right in almost every way. 

Go out there and start dating now. More articles are on the way to assist you to improve your chances significantly. Don’t let fear stop you. 

They’re out there, waiting for you to find them! 

Get ’em, Tiger! 

Courtesy of iStock.com/adamkaz.

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