9½ Important Things To Realize Before Dating Again


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One of the biggest pieces of dating success is the way we approach how we get to know somebody new. We have all faced heartbreak, challenges, and emotional pain. Whether we are coming out of a long term relationship, a marriage, or just a long time without dating – getting back out into the ‘scene’ can be a little intimidating.


To make the process easier, here are a few things to keep in mind before you jump back into the pool.

1. Understand someone new is not someone old.

When we have been with someone for a long time, it is natural to use them as a benchmark for the ways someone acts. We think back to the good [and bad] and try to make comparisons with the new person. While we should be aware of similar red flags [ie., a short temper or violent tendencies], we also have to keep in perspective that this new person is completely unique from the old, and should be given a fair chance to show it.

2. Make sure your past relationships are in the past.

Of course we will carry with us a piece of every experience we accumulate in our lives – that is how we become the person we are today. But it is important to keep the past in the past and heal ourselves before we will be able to give again. We have to be emotionally available if we want any hope of forming a real connection with someone.

3. Know that dating is a numbers game.

It is easy to become discouraged if you go on a date with someone and it doesn’t work out. Or two people. Or three…or 20. But what we always have to keep in mind is that dating can be a numbers game. With seven billion people in the world, only one will be the person you end up with. We have to be open to this taking some time, and doing our best to not become jaded. It is sort of like playing the lottery – you may have to lose a lot before you win, but you’ll never win if you don’t play.


4. Dating is supposed to be fun.

I can’t tell you how many times I have heard people complain about the dating process. What a pain it is, or how expensive it is, or that it is tedious or time consuming. Dating is supposed to be fun! You are spending time with someone you are attracted to and is attracted to you in return. You are getting to know a unique person and determining whether or not you want to spend more time with them. You are experiencing new things with a new person.

If you’re not actually enjoying the process, it’s a good sign you are going out with the wrong person.

5. Don’t cling to the first person you see.

Especially if you are coming off of a longer term relationship, you may be used to the comfort of having someone there all the time. Someone to text during the day, someone to come home to. Someone to share your important [or unimportant] news with. For this reason, it is tempting to look for that comfort anywhere you can find it.

We have to make sure that the person we are spending time with has our attention because of who they are, not because of the idea of who they are. Do not simply force a puzzle piece where it doesn’t belong in order to fill the void quicker – make sure it is the proper fit.

6. Don’t forget the lessons your past taught you.

While it is important that we leave our past relationships behind us [See #2], it is also important that we always remember what it taught us. Not all of our relationships are meant to last – but they will teach and prepare us for the one that does. Try not to see it as a waste of time – if it didn’t bring you what you wanted, it showed you what you don’t want.


7. Be flexible with your “type.”

Sometimes, the best people are the ones who come into your life by accident and stay on purpose. If we keep dating the same types of people, we will likely keep getting the same results. Be open, be flexible, and be aware that the right person for you may not be who you expected it to be.

8. Be proactive.

I think one of the biggest reasons people stay unhappy – both in life and in love – is that they wait for things to just happen to them. They want to be swept off of their feet somehow during their daily routine. They want to all of a sudden get that promotion without going above and beyond because they ‘deserve it.’

The truth is that a great life is not just something that happens to us. It is something we have to stand up, go out, and create. This goes for all areas of life, and definitely dating. If we are not actively improving ourselves or pursuing hobbies that put us around people we share similar interests with, or even setting up online dating profiles – we cannot wonder why somebody didn’t just knock on our door and pick us up off of the couch.

9. Always be up front and honest, while expecting it in return also.

One of the biggest issues these days is miscommunication. A quick glance through Facebook comments shows us that most adult humans can’t even grasp the difference between “your” and “you’re,” let alone effectively use the English language to carry on an entire conversation [texting]. Aside from that, if we do not clearly state our intentions, how can we expect the other person to know what they are?

One of the biggest complaints I hear is about people not being genuine about what they really want. The only thing this can lead to is misconceptions and heartbreak.


9½. Learn to be happy being single first.

Here is the ½, because this involves just one person [you] and not two. The best way to prevent rushing into something new with the wrong person is to be happy and content while you are on your own. This way, you will more clearly be able to see a man or woman as an addition to your life, not as a required piece of it.

Great relationships are not about two people who complete each other, they are about two people who are already whole and accept each other completely.

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  1. lauranatalie1 on November 19, 2014 at 4:12 pm

    Reblogged this on InsideMyShoe.

  2. Carol Vincent on November 19, 2014 at 9:05 pm

    “Effectively use the English language”….number 9 of the list.

    James, those few words speak volumes. Pithy summary…excellent and sadly amusing.

    Your column is a pleasure and thought provoking no matter the age nor gender of your readers.

    To your continued insights and articulation,

    Carol Vincent


  3. Sabrina on November 19, 2014 at 11:12 pm

    Good reminder for those who are in relationships too. Especially #8. You have to be proactive in everything if you want something to happen. Thanks for the post!

  4. brendaxyz on December 23, 2014 at 4:06 am

    Reblogged this on Brenda..

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