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It is not uncommon in the dating scene to come across some incredibly beautiful women. There is something to be said for meeting a woman whose physical beauty transcends age. Take Jennifer Lopez or Halle Berry. Both women are in their late 40s by birthdate but hold it down like some women who are half their age. Most guys wouldn’t care how old those women are – if they had a chance to date them, they would.

You meet a woman who’s beauty does just that – transcends her age. She is so beautiful you don’t care how old she is – you’ve got to get her. For sake of this article, we are talking about a woman who is significantly older than you. Let’s use 5-plus years as a proxy. Chances are if she is 5-plus years older than you, there is no chance you could have attended a school at the same time. None of this matters all that much to you. She is fine, cool, successful and most important wants to date you as well. Here are some rules for dating an older woman:

  1. Make sure you share as many mutual interests as possible – The idea of dating someone who is the total opposite of you is cool – in theory. You better make sure you share a lot of common interests. You can’t be into hip-hop and she hates it. She can’t be into going to art galleries and you can’t stand them. The age difference is a convenient excuse but the importance being able to do things together will help remove some of the focus from the disparity.
  2. Meet her circle of friends as soon as possible – Her circle of friends will tell you a lot about where she is in her life without having to ask. We are all but a sum total of the people we surround ourselves with so the importance of seeing her circle can’t be overstated. Are her friends married? What is the age range of her circle? Are they supportive of her dating you?
  3. The older she is, the more likely she is set in her ways – The saying goes that you can’t teach an old dog new tricks. The same goes with people. She is used to doing things a certain way. She might switch up in order to please you. But don’t hold your breath. She is good where she is. She will probably expect you to get on board with her way.
  4. She will not always value your voice or experience as a man – This is a big one. The reality is that she has been on this earth significantly longer than you. If you try to give her advice (particularly unsolicited) and she doesn’t want to hear it, she will not heed it. Even if you are right, it won’t matter. She is older and in her mind wiser than you.
  5. If she has children, they might not respect you if they know your age – This totally depends on her age and the age of her children. If they are younger, probably not an issue. But if they are in those teen years, know how old you are compared to their mother, are hormonal and don’t like the fact that you are giving it to their mother – look out. You could be a nice guy. You could be a good man to their mother. You might even take an interest in them. Doesn’t matter. They probably won’t respect you.
  6. Probe her dating and relationship history – You want to get an idea of whether or not this (dating a significantly younger man) is a habit or anomaly. You want to know about this for a couple of reasons. One, you want to get an idea if you were a target because of your age. This might seem strange but there are some (not all) seasoned women who specifically go after younger guys. These are commonly known as cougars. You want to avoid them. Secondly, you want to know whether or not she has formulated ideas about dating a younger guy. More expressly, you want to get an idea of whether or not she will loop you in with those ideas or expectations. You are an individual and need to make sure will be treated as such.
  7. The “luster” may wear off faster – Part of the novelty of the relationship is that there is a significant age difference but yet you’ll are together. How long will that last? Who knows? But it may very well reach a point where one (or both) of you is going to miss things about being with someone closer to your age. I am not suggesting that this will be the demise of your relationship. But it is important to address in the issue when it comes up. Which leads to number 8…..?
  8. The age difference is a convenient excuse to use when things aren’t going well – When you are not seeing eye to eye or arguing it is easy to go to “he’s too young to get it” or “she’s so old, she won’t ever change”. That is trash. The issue at hand must remain the issue. Going to the age difference is an easy and lazy cop out. Rarely, if ever is your age difference the reason why you’ll aren’t seeing eye to eye. People in relationships will disagree. That is a fact. Men and women disagree. Another indisputable fact. Focus on this issue, not the age difference.
  9. Certain conversations will need to happen sooner than later – If she’s a woman of a certain age who doesn’t have any children but wants them you must consider that before you become involved. The fact is that you as the younger party and male have more time to consider the children question. She doesn’t have that luxury. She has to consider the biological clock. Find out early on if you’ll share that desire for children. Especially so you can discuss a potential timeline.
  10. Be honest about the situation – Early in any situation, it is easy to get lost in the newness of it. But the fact is there are multiple things you absolutely have to be honest about with yourself. She is older. Will you remain attracted to her physically as she starts to age over the long term? Who knows? He who is not honest with himself about the future will doom his present.

Obviously, there are more but you get the general point. No one is telling you not to date an older woman at all. You just have to consider everything that comes with it before you committing to the prospect of a long term relationship. It is also likely that because of her age, she is not in it for just a good time. Consider this: if you reach a point where you feel like it’ll be a waste of time in the long run to date her, it is not just your time that you are wasting.

A man's deepest fear shouldn't be that he's inadequate; it should be that he is not pushing himself to be what he is meant to be - Max

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