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10 Gay Dating Rules for Men Over 50

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Posted by Joseph on December 23, 2014
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It’s Never too Late to Teach an Old Dog New Tricks!

Dating as a mature gentleman opens up a whole new perspective on love. Men of a certain age are used to the old school system of thought and practice – you ask a guy out, you have some fun, you fall in love, and you start a family. Well, when you’re entering each other’s lives a little later than usual, chances are, they already did all that with someone else. And so did you.
Reigniting love is easy, but when you’re older there are certain things you just need accept in a partner that you might not have been able to accept as a younger chap. You’re not in your twenties anymore so the whole idea of planning for your long tern future is somewhat out the window. But trust me when I say this is a great thing. When you’re older, you are much more settled, which means all you can offer each other is NOW. In the moment. That’s one aspect of dating most twenty-somethings can’t comprehend at the present time.

1) Know the Man You Are TODAY, not the Man you were 20 Years Ago
Life is a bitch. When you’re dating in your 50s, there’s a huge chance you’ve been bitch slapped by life either through a breakup, death, or a vast amount of negative energy. These types of things force you to be chronically unsatisfied. It’s time to find contentment, but it starts with owning yourself first. Before you rush out looking for love again, you need to know your value.
Fall in love with yourself first. This is a major step towards finding wholeness and acceptance of the things you cannot change. Your past is in the past. Ask yourself what you think of you, not what the world thinks of you. Our world (parents, friends, coworkers) are always brainwashing how we view our self-worth. We value their opinion so we can’t help but take their statements personal, but never should you give them an opportunity to change your mind about your potential.

2) You Need to Throw the Old System Out the Door
Every time something new seeps into the world, there are always those who refuse to conform simply because they’re used to the old way – radio, TV, cell phones, computers, apps, online dating, etc. Dating in the 21st century is totally different than it used to be, and it’s changing every day. Guess what, social media wasn’t a fad after all; it’s actually one of the only ways people connect nowadays. Oh and by the way, online dating is here to stay too. Pew research shows that 8% of people between 45 – 54 years old are dating online. It’s time to be a little less stubborn about joining the digital world.
Romance still exists, that’s a fact. It’s out there for you to grab, but the way you find it no longer resembles an old black and white film. There are new digital ways to find a connection, or at least secure a connection. You might meet a man at a friend’s party rather than online, but have you thought about exchanging Facebook information? Or at least giving his name a Google search to learn more about him? The whole world is literally at your fingertips, so it’s time to discover it. The new communications system is digital. Like it or not, it’s here to stay.

3) You’re Selling Attributes Can’t Be Artificial Anymore
When we’re in our twenties, it’s all about youth and beauty. Gay guys worship them and we learn early on that it’s an accurate way to judge our value and potential. It’s sad, but true. Men are visual creatures who judge physical appearance, so we seek every opportunity to enhance ourselves (it’s sad but true). Our image is everything. Hair, skin, clothes, nice body, great sex skills are prominent attributes when you’re dating in your twenties because you have your whole future to find Mr. Right. Who cares about a few little duds? But by the time you reach fifty, you’ve been there, done that, seen it and bought the T-shirt. You need a little bit more than a full head of hair to decide proper compatibility.
Security, generosity, compassion, self-ownership, confidence, flexibility, and common interests reign supreme. There are plenty of older gentlemen who enjoy the company of younger guys, many of whom are unconsciously trying to grab a bit of their youth back. This is all fine and dandy, but a twenty-two year old has next to no experience when compared to a fifty-four year old. Young people have different worries, different goals, or different ideas about the world. I’m not saying they’re not out there, but there a dime a dozen. If you want a partner in every sense of the word, it’s time to be a little less artificial about choosing men. Clearly, that’s gotten you nowhere thus far.

4) You HAVE to be Willing to Make Compromises with Yourself
He might have a few ticks you were less able to accept when you were twenty. He leaves the TV on at night, he eats sandwiches without a proper plate on the table, he drinks a tad too much when out with his friends, his political views aren’t exactly up to par with yours, he pees a little on the toilet seat, etc. As you reach your late twenties and thirties, you learn how to not let the small things affect you. Now is the time to put it into practice.
You will be much less stressed picking up the crumbs yourself rather than letting it bubble up inside, only to blame him for it later. You can voice it to him, but sometimes you just have to let unimportant things go. The last thing you want is to be naggy. It creates resentment that distracts you from seeing your true feelings. If he’s worth it, you have to be willing to make tiny compromises in regards to pet peeves. Don’t sweat the small stuff. Look at the bigger picture and start owning a piece of it.

5) Never Wait to be Chased
Waiting is wasting. It’s stupid to sit back and wait for a man to come find you. Imagine how many people have passed you by because they assumed you weren’t interested by the way you handled yourself. If someone is still playing the lost princess in the tower scenario when they’re fifty-five, shouldn’t that say a lot about how secure they are within themselves? There’s literally nothing to lose. A simple hello, a smile, or even a dinner date means nothing.

6) There’s a REASON Why They (and You) Are Still Single
The first month of any relationship is bliss. It’s exciting, passionate, and the best times. But it’s also the window where you’re likely to spot red flags. When you were younger, you spotted these red flags and ignored them. You know this always leads to trouble. Now that you’re older, you’re more likely to start investigating these red flags as signs.
There’s a reason why people are still single when they reach fifty or sixty, and that includes you. During the early stages of mature dating, it’s important to give a review. Did your past relationship show similar signs, red flags, issues, and hindrances? If they did, you’re likely to run into similar problems. Clearly it didn’t work out last time, so what makes you think it can this time? But, like I said in #3, you have to make a decision if he’s worth it. If he is, waste no time in trying to handle situations before they arise.

7) Baggage is Inevitable. You Just Need to Accept It
There is a huge chance he’s had plenty of long-term relationships in the past. They all ended just as yours did. He might have a few undesirable traits in a boyfriend (as might you). The reality of mature dating is that there’s always going to be issues to deal with in relation to health, finances, or family. They are first-generation survivors, they know the importance of community, they may have had an ex-lover die in the last few years, they might have an ex-wife and kids, or they might not be willing to come out just yet for business reasons.
Baggage comes with every new relationship, but as you get older it’s expected. And it’s not petty baggage like, say, a dog or an apartment lease. It’s heavy stuff, like child support, child custody, a lack of investments or declining health. You might find a great guy your age on the same level as you, but dating while you’re older is going to come with the type of baggage you’re going to have to accept. That’s a reality.

8) Know Early On if You Should Stay or if You Should Go
Let’s fast forward a few dates. Do you think you’d still be happy with him? Can you envision having Christmas with him? Birthdays with him? Work parties with him? Introducing him to your kids and family? Is he reaffirming how you feel about yourself, or is he making you feel a little less than what your potential can be? These are all things you need to recognize at the beginning.

9) Never Let Dating Lose Its Appeal
Dating might feel like it’s lost its appeal. You might not be young and vivacious, but that doesn’t mean you can’t enter the dating world with enthusiasm and optimism. You need to be eager to get yourself out there. Don’t hide in the confines of your apartment too scared to show yourself. Being open to finding a romantic connection doesn’t mean you have to do it in a naïve way. It doesn’t mean you’re vulnerable nor does it mean you’ve lost your game. It just means you have an open heart.
When you’re older, you get much more realistic. This I know. Dating a man isn’t about having one night stands anymore. It’s about finding compatibility. You’re ready to settle down and you’re much more eager to settle, but trust me when I say you can’t take the first guy who enters the picture simply because you’re desperate to find Mr. Right or Mr. Next. Spread yourself out and window shop. Dating is supposed to be fun. You can still be realistic in the process, but never let the appeal of dating turn you off. The second that happens you’re most likely to hide under the covers for all eternity.

10) Stop Having Unrealistic Expectations
This is a major thing we all need to get real with. You can’t set the bar so high that it’s impossible to reach. The things you expect in a boyfriend when you’re 20-something shouldn’t be parallel to what you want now. Eventually, they’re going to conflict because the only types of people you’re going to attract are young boys and/or older men who act like boys. Start looking for men who want the same things you want rather than guys who already know are short term.
Take some time to reflect on the qualities you want in a man which are sensible, not artificial. Start with the lessons you’ve learned from the past and make sure never to repeat them, i.e. a man who’s totally independent, children who aren’t toddlers, who lives at least ten miles away, and other similar issues you’ve run into before. Let those lessons guide you towards a better direction instead of playing the game like you’ve always played it.




Have you found the right one, or are you still searching?
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