THE BLOG
08/18/2016 06:06 pm ET Updated Aug 19, 2017

Re-Entering The Dating World After Many Years

As we all know, dating can be tricky at any age, but it can be especially so in older dating, or when dating after a very long-term relationship. It may have been quite some time since you have dated, as you have been married, or involved with someone for years. There is a good chance that at the point that you had your last long term relationship, the roles and rules of dating may have looked quite different. Many men may face women who are bolder and the aggressor in the relationship, and are not sure how to navigate that.

At the point when they entered their marriage, many years ago, people were in more traditional roles. Many have not had to let someone down gently in quite some time, so they have forgotten the common courtesies of letting someone go gently and with grace. There may not have been a world of online dating apps, dating sites, texting over calls, or people who want to go "dutch treat." It is a strange new world, and it is important to have patience, an open mind, and a willingness to grow and change with the changing dating world around them.

The first point to consider is the situation in which the women is the one who makes the first move, and the man is not used to things not being on his terms. This can be jarring the first time it happens, but this is actually quite common now, and is not a sign that the woman is too forward, that she is only looking for a good time and nothing serious, or that she does not think highly of herself. She just believes that you are equals, and that it is ok to let you know that she is interested in getting to know you better. Take it for the compliment that it is, and keep an open mind.

Another very important issue is the common courtesy of letting someone down with grace and kindness. It may have been many years since you have had to tell someone that they are not for you, or that you do not feel you are a match. They may not be right for you, but that does not mean you cannot be kindhearted and gentle to the person. In this digital age, many people will do what is called "ghosting" someone, where they simply cease all communication, and never give the person a reason why. You are all too aware that there are better ways to handle this, and that as a person, you would hope for some kindness and courtesy. The person may not be right for you, but it takes virtually no effort to tell someone, "I don't see things working out between us, but you are a good person, and I know there is the right person out there for you. I wish you the best in your search." Simple, classy, and closure!

Over these last years, there are many way things have changed. With dating apps and sites, with empowered and successful women who want to pay their own way, with the women being the one who asks you out first, but in many ways things have stayed the same. Remember that at the heart of things, the goal is for two people to meet and make a connection with each other. That fact has never changed. The way they meet, communicate, and what they do for dates might be slightly different, but change is not always a bad thing. Perhaps this second chance is the chance you have been looking for. Perhaps all these new ways of meeting people and dating will allow you to find someone you may have never found otherwise. Perhaps, dare I say, you may find the person that you have always been looking for. Someone who is that true fit for you, and who appreciates and loves you just as you are now. While sadly, things may not work out for our first attempt at a life with someone, there is a chance that an even better match is out there waiting for you, if you keep an open mind and heart.