Dating Over 40: Middle Aged and Kickin It

Dating Over 40: Middle Aged and Kickin It

Whether you’re just divorced or are pulling your head up above your career-focused life, dating over 40 can feel very daunting and challenging. If you’re just out of a relationship, you’re experiencing not only the feelings of loss, but also the angst of wondering if and when you’ll find someone new.

If you’ve been career-focused for the last few years, that’s okay, but you most likely still have the anxiety associated with dating, along with a few stigmas and myths about dating over 40.

Rest assured that I’ve got all aspects of this covered for you today! First, we’ll talk about those myths of dating over 40 and determine if any of them have any validity.

Then, we’ll look at how you should approach this new dating life you seek.

Finally, I’ll share some common mistakes women over 40 make when entering or re-entering the dating scene.

I’m ready if you are!

Dating over 40 Myths

Myth #1: All the Good Men are Taken

Whether you’re looking online or in person, this simply isn’t true. Are there slimeballs out there? Yes! BUT, if you’re a confident woman when your stilettos hit the dating scene, those slimeballs will steer clear of you.

The truth is that if you go into dating assuming that all the men you find are not good men, that’s exactly what you will find.

Great men can sniff out a jaded woman from fifty paces, just like they won’t approach a woman who lacks confidence, so going into dating over 40 with this mindset will indeed cause you find only slimeballs, but not because the great men aren’t out there. They’re just avoiding you because they see you very clearly.

The truth is that there are millions of single men over 40 and they’re looking for the same thing you are, a healthy, happy relationship.

Of course, there are those out there who are catfishing and you need to learn how to be on the lookout for them, but going into it thinking that every man is a schmuck won’t get you anywhere.

Myth #2: I’ll Only Date THESE Men and I’ll be Fine

If you’ve been in a relationship or two, you’ve likely also been bitten by a bad relationship or two. This often causes you to form a list that goes something like this:

  • I’ll only date college-educated men
  • My man must have a professional degree (doctor, lawyer, etc.)
  • I’ll only date men who are six feet tall or taller
  • I won’t date men with children
  • Men who ride motorcycles are OUT
  • The man I date must be a true gentleman

I could go on and on, but I think you get the idea. While it’s fine to have a list of things you’re looking for in a man, it can also fix the situation so no man will ever meet your criteria. This is actually your dating fear hard at work.

Create a list. Go ahead. I encourage it. But make this list with knowledge and be flexible. Go back through your past relationships and make two lists – one of things you liked about each man, and one of things you didn’t like about each man. Find the things that repeat on those lists, like college education or profession.

Those are your guidelines. They aren’t hard and fast rules. There will be one or two must-have and must-not-have items on your list, but don’t make every item a must.

The man you’re attracted to may surprise you, but you’ll never find him if you aren’t flexible.

Also, don’t include too many superficial items, like how they look or how much money they make.

Think of your own values and goals in life. If you value hard work, you’ll want someone who does also, regardless of the color of his hair. If you want to retire at fifty-five and travel the world, a family man might not work out very well.

Myth #3: All Men in Online Dating are Liars

Whenever you use all or nothing phrasing, you’re asking for trouble. Not all men in the online dating world are liars, well, not about the big stuff anyway. Lying on a dating profile can probably best be described in degrees.

Everyone lies about the last ten pounds, hoping that when you meet, it won’t matter. Everyone posts the absolute best picture of themselves, regardless of the fact that it was taken five years ago. Generally speaking, those lies are harmless enough.

What you need to look out for are men who try to pull a fast one on you to get money from you. Hopefully, you already know not to send money to a stranger, and yes, he is a stranger. I don’t care how many emails and messages you swap, he’s a stranger.

Dating Over 40 Myth #4: I’ll Lose Myself

It’s so easy to get comfortable in the life you’ve built, and a common misperception is that if you start dating, you’ll lose who you have worked so hard to become.

This is a low-confidence fear centered around not having enough boundaries to protect that woman you’re working so hard to become.

Before entering the dating scene, it’s important that you build that dating confidence and learn what boundaries are necessary to help you maintain your sense of self.

We attract people who are most like us, so if you want to attract kind, confident men, then you must become that woman. The boundaries you set will help you hold onto your confidence and kindness, or whatever other attributes you find important. This goes back to that values conversation we had a little bit above.

Determine what your values are and live up to them. Set goals around them and work toward those goals. Set boundaries around those values and protect your journey to achieve your goals.

You won’t lose yourself in the right man. The right man will join you on your journey, value many of the same things you do, and help you maintain the many layers that make you the woman you are.

Myth #5: I’m Not Good Enough

This is another low confidence, low self-esteem myth. I read a phrase that rings true in this situation – it’s called obsessive comparison disorder. This is when you spend too much time comparing yourself to others.

Nobody has traveled the road you’ve been on. Nobody is exactly like you, so comparing yourself to anyone else is like comparing apples to oranges. It’ll never work, but if your self-esteem is low, it will always confirm your beliefs that you aren’t good enough.

Let me ask you this. What aren’t you good enough for? You’re certainly good enough to have happiness. You’re absolutely good enough to be worthy of a great man, and I know without a doubt that you’re good enough to deserve a loving relationship.

But you won’t believe me, and if these types of thoughts are banging around in your head on a regular basis, it might be worthwhile to seek professional help. These thoughts usually originate somewhere else – like a parent who always told you that you weren’t good enough when you were growing up, either in words or by their actions. It can also come from dating verbally abusive men in your past.

Regardless of the source, a professional can often help you overcome those thought processes and set you on a course of happiness.

Dating Over 40 Myth #6: I Have Too Much Baggage

Imagine a great man who was handsome, has the same values as you, has similar life goals, and seems confident and solid introduced himself to you. If you found out a few dates in that he has two kids, an ex-wife, and a demanding job, would you dump him, just because of those things?

Unless you totally hate kids, you’re probably saying, “Heck NO Gregg! Send me that guy!”

So why do you think having those same things in your life makes you unattractive to a man? Men in their forties don’t expect you to be a twenty-year-old teenager with a perfect body, no kids, and all the time in the world to dote on them.

Most men in their forties are just like you – looking for love the second time around. Sure, one or two of them might be looking for a much younger girl, but even those men often learn that a twenty-year-old isn’t all she’s cracked up to be.

The truth is that your baggage isn’t any heavier than that of most other people your age. Young people also have baggage, just different baggage. If something comes up, focus on what you learned from the experience, instead of the negatives of the event. A confident man will appreciate the learning experience.

Dating After 40: A New Approach

Step One: Take Some Time Off

While your gut, and maybe your Aunt Mary, are telling you to get right back out there and find a new guy, that’s your insecurity talking.

You’re better off to take some time off to heal and to prepare yourself for love again first. The sooner you rush back in, the more likely you are to find the wrong types of men.

Step Two: Check and Rebuild Your Confidence

If you were to evaluate your confidence right now, what would you say it is? Low, medium, or high?

Maybe if I give you a definition of confidence, you’ll be better able to assess it.

Confidence is feeling sure of yourself and your abilities, not to the point of arrogance, but in a realistic and secure way.

By definition, you can have high confidence in some areas of your life and lower confidence in others. For example, if you’re a great artist, your confidence in your artistic ability is probably pretty high, but if you’ve been through a few bad relationships, your dating confidence may be low.

So, if I ask you again now, what’s your confidence, and I narrow it down to dating, what is your reply?

Once you assess where your confidence is, you can boost it as needed. Each area of your life will be a little different as far as bringing your confidence up, but if you work on yourself in general, you will find that it raises across the board.

For example, if you really want to work on your dating confidence, get a friend and go out for an evening to a place where you believe you’ll see single men. This might be a local pub or a jazz club. It might be a volunteer opportunity or some other type of event, like a wine tasting.

The key for this outing isn’t to get a date, but merely to bring yourself to smile at a few men who interest you. If someone walks by and says “Hello,” it’s okay to reply with a quick hello. All you’re looking for here are a few innocent interactions.

Step Three to Dating Over 40: Be Patient

Dating isn’t a sprint, it’s a cross country stroll. Men and women view dating in very different ways, much like they view everything else.

Don’t rush the process. Linger and enjoy it. Dating is meant to be fun, but we often put too much pressure on ourselves, and it makes it more like a chore.

Be patient. If you’ve built your confidence, you’ve put an armor around yourself to deflect the losers and players. Once they sense your confidence, they’ll avoid you and move on to an easier target. The confident men you’re trying to attract will be drawn to you.

But don’t find one guy and latch on for dear life. Date several men at once and figure out what you really want. I know this goes against what you think, but you don’t have a commitment to these men yet and I guarantee that they’re dating other women.

This also means not applying pressure to become exclusive too soon. Dating should be fun. The sole purpose of dating is to figure out if you’re a good match and to learn more about one another.  Too often, many women view each date as a step toward the alter. Drop that mindset and just enjoy the process.

Get to know the men you choose to date. Do fun things on dates instead of dinner dates. Go hiking, bowling, to a sporting event, or whatever activities interest you. These are real life activities where you can see how he responds to real life situations.

But most of all, be patient. Don’t rush things. Date several men and slowly weed out those who don’t feel like a good fit. Most importantly, never give a man the right to have sex with you until he’s proven himself worthy of you!

Step Four: Try New Things

You’re single now. It’s time to branch out! And don’t tell me you can’t because you have kids. If they spend time with their father, you have that time. If they don’t, you can always trade babysitting with a friend or ask a family member to watch them for you.

Try new hobbies. Learn a new skill. Plan a trip, even if it’s just for a day, to explore new places. What have you always wanted to try but you’ve been afraid to do? It’s now time to go for it!

This gives you another benefit. You’re adding chapters to your story, and exciting chapters at that! No, a man might not be interested in quilting, but he’ll be fascinated by the process of cutting large pieces of fabric into small pieces, only to put them back together into another large piece. He’ll be totally intrigued by how you get the wick to stand up in a candle.

When you go out on dates, you have these new experiences to share, and that makes you mysterious.

When men date, they date to have fun. When they meet a woman, the best thing about her is often that she’s a complete mystery. Men love to unravel the mystery, one bit at a time and coming to a date with the news that you just tried scuba diving for the first time or that you walked three chihuahuas, a beagle, a German shepherd, and four yorkies earlier in the day will fully intrigue him.

Step Five of Dating Over 40: Get Up to Date

If you haven’t been in the dating scene in a few years, you need to realize that things have changed. The longer you’ve been out of dating, the more things have changed.

This isn’t just true about dating apps either. Dating in general has also changed, for better or worse in some cases. Men don’t always come to pick you up for a date – you meet at the venue. This is a good thing if you’re meeting someone from an online dating site, but it’s also a good idea for the guy you met last week while watching football at the pub.

Ask your friends who’ve been dating for a while how to navigate the dating scene today. Read up on the assorted apps so you know which ones are for hookups only and which ones are more about what you want.

Other Tips on Dating Over 40

Don’t Follow ‘Old Fashioned’ Etiquette

Back in the day, a woman sat and waited on a man to reach out to her. That’s one of those things you need to get up to date on.

Women reach out now. Whether it’s in person or online, it’s okay for you to approach a man you’re interested in.

Don’t just put a profile online and wait for men to reach out. Put up a profile and then start winking, giving a thumbs up, or whatever to men you find appealing.

If you’re out with your friends, don’t be afraid to offer to buy a man a drink or challenge him to a game of pool. This is a show of confidence and strength that a confident man will admire.

Don’t Say “Yes” to Every Inquiry

Yes, I told you to date other men and yes, I just said you should be proactive, but that doesn’t mean you should say yes to every inquiry a man makes.

Every man who reaches out on an online dating app won’t be for you, and just because you find a man visually appealing doesn’t mean he won’t turn out to be a frog later.

You’re under no obligation to date anyone. Even if a guy buys you a drink, it doesn’t mean you owe him anything, just like you buying a man a drink doesn’t mean he owes you anything. Never let a man, or anyone for that matter, pressure you into something your gut is saying no to.

Saying “Yes” to everything also will exhaust you. While it’s important for you to get back out there, it’s also important for you to maintain the singles life you’re building, even when you start dating just one guy.

Set aside time for hobbies and time with your friends and keep that time, even after Mr. Wonderful comes into your life (and let him keep those things for himself too).

Don’t Make Elaborate Date Plans

I mentioned earlier that dates should be fun. Yes, the traditional date is a dinner or coffee, but that doesn’t provide you with the privacy you need to get to know one another, nor does it give you a good glimpse into who you each are.

Plan a date in public where you can do something fun together and still be visible to others, without having people breathing down your neck. I mentioned bowling before. This is a great first date because it’s something very few people are good at, so you can easily get caught up in laughing at your abilities or using bumpers to keep from throwing gutter balls.

You’re out in public, but you have your own lane, many offer food and beverages, so you can still eat if you want, and you get to know his personality under more ‘natural’ circumstances.

Look at Early Dates as Meetings

This is especially true if you’re meeting someone you met online. Set a time limit of maybe thirty minutes for the date. Agree to meet in a public place, and then stick to your guns.

This isn’t a date, regardless of what verbiage you use when you plan it. Try to keep using the words meeting and meet instead of date. This sets a different expectation.

It is a meeting where you get together with your new friend and determine what, if any, chemistry may be between you. Enjoy a tea or coffee and relax. If you don’t like him or he doesn’t like you, it’s okay. It’s a meeting, not a lifetime commitment.

If you view your first few dates in this way, it will take some of the pressure off of the experience and will help you be less emotional during the meeting. This, in turn, helps you use our logical thought processes instead of emotional.

Don’t Rush into Sharing Your New Beau with Your Kids

Your kids are not dating your new guy, but they will ultimately. Still, this doesn’t mean you invite someone you’ve known for two weeks to meet your children.

For one thing, you should be dating multiple men at this point, and parading multiple men in front of your kids is a poor example for them to see.

Wait until you know a man before you introduce him to your kids. While there’s no specific timeline for this, you should at least wait a couple of months.

Of course, I’m assuming also that you didn’t get divorced last week and now you’re dating someone new. You’ve taken some time off and rebuilt your confidence first. In doing this, you also give your children time to adjust.

Be Patient with Sex

Insecurity forces women to have sex with men sooner than they should. Any man who makes it seem like you either must have sex with him or lose him altogether is worth losing.

A great man may insinuate that he wants to have sex with you, but he will respect you more if you make him wait and earn it.

No, you won’t lose him, and if you do, good riddance. He’s not the great guy you thought he was.

The exception, of course, is if you’re just in it for hookups, but I’m assuming that if you’re here, that’s not what your ultimate goal is.

Wait until your relationship is headed in a good direction. You’ve weeded out the other men and you’re feeling pretty good about this guy being a keeper, at least for now.

A man will respect you if you make him wait. It shows him that you respect yourself and have boundaries. Those are both good things!

Trust Your Gut!

Your intuition is your best friend. If your gut is telling you there’s something hinky about a guy, listen. Chances are that your intuition is right.

Too many times, we ignore our gut instincts, only to later wish we’d listened. I’m sure if you think back, you can recall a few of those instances in your own life.

Don’t Get Upset with His Outside Life

Now that you’re in your forties, your life is more complex. When you were in college, you had your studies and maybe a part-time job to worry about.

Today, you may have children, professional obligations, workout routines, and hobbies that keep you busy.

So do men.

If a man tells you he can’t meet with you at a desired time, it’s okay, unless it becomes a habit. Things happen. Plans with the kids change, work demands creep in, and other things come up.

Additionally, you might not be the night owl you once were, and neither is he. Dinner at seven might be too close to bedtime for both of you.

Just don’t try to read between the lines if he changes your plans. It might mean that he legitimately has something else he needs to do.

Dating Over 40: That’s a Wrap!

Dating over 40 might seem like a scary thing, but if you take some time to regroup, rebuild your confidence, and are patient with the process, you’ll thank yourself later!

Dating requires patience, regardless of your age, and confident women will always draw confident men into their orbit.

If you’re patient, you build a life outside of dating, you will find true happiness and a rewarding relationship.

Are you Middle Aged and Kickin' It? What I mean is are you one of those fortunate women who finds herself a little older than a teenager and looking for love? Things change and it can be tough to keep up with the dating scene. That's why I wrote this best-seller for women just like you. Maybe you've been in a relationship for a while and you're now getting back out there. Where do you start? What do you do? All those questions are answered for you! Learn more about the book here or buy it today by clicking one of the buttons below.

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