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Photo by Charlie Foster, from Unsplash.

Dating after divorce is scary, but it doesn’t have to be.

5–checkpoints to navigate to a healthy new start.

Karen Kindred
Mar 13, 2016 · 5 min read

Dating after divorce is scary. (And when I say divorce, I mean any relationship that has gone on for years whether there was a legal marriage or not.) Let’s just say you were with someone for twenty years. You were in your twenties. Now you are in your forties or fifties. You probably have children, a home, friends, a community. Now your life is not at all like it was. That in itself is terrifying, even if you wanted out of the relationship. And not only have all those elements changed, you have to deal with a whole new world out there.

Technology has completely changed. There are so many new ways to meet people, yet for some reason you don’t. Or you are meeting a bunch of “crazy” people. Navigating social media, dating, avoiding the same mistakes, looking for red flags, and dealing with your self confidence and body image is overwhelming to say the least!

The fact is, you’re going to want to get out there again. People still need relationships because we are all looking for connection. No one wants to be alone forever. There is no right or wrong way to handle this, there are just healthy ways verses unhealthy ways. The choice is yours. It is very important that you prepare yourself mentally, emotionally and physically to get out there.

I have helped many clients navigate to their “new normal” and there is a common path consisting of five important checkpoints:


You want to start out meeting new friends. If you have been in a relationship for some time, you will most likely find yourself feeling alone, and at times a third wheel. Most of your couple friends will genuinely want you to join them.

Don’t let your feelings of intruding stop you from joining others. You never know who you might meet. But if you can even find one friend that is single that will create a new network. You can begin doing things with that person. (I am referring here to some one who you do NOT want to date. It doesn’t have to be, however it is generally less complicated that way.)

Start out you doing things you both enjoy: sports, exercise, movies, dinner. Anything that just gets you out. Spend some of your time talking about what’s going on in your life, many times they have been there in the past and can offer support. They may even be in about the same process you are and that can be a support to both of you. I strongly caution you to limit the time you spend getting into the hard parts of your life. We all have bad days and we need to get pulled out of them and that’s okay. It is healthy to spend maybe an hour sharing and supporting each other, after that it becomes too consuming. If someone is spending too much time talking about the horrible things in their life then you need to speak your truth and tell them it’s too much! The purpose of this friendship is to have fun and meet other people. You will be surprised how someone knows someone else and then someone else. This develops into a group! Now you have a number of people you can call and make plans with. Having plans and looking forward to fun things is so important to being happy.

Make sure you have good boundaries with your friends. You need to learn to be by yourself some of the time and you need to start working on dating.

CHECKPOINT 2: Your mental well-being.
There are so many conflicting feelings. Sadness, denial, relief, a sense of failure, shock, anger, resentment, bitterness, distrust, FEAR! So many emotions you are cycling through sometimes daily, sometimes hourly, sometimes minute to minute. Be aware of your thoughts! Notice the things you are saying to yourself. If they are mostly negative then you need to work on changing those thoughts. Check in with yourself and make sure that most of the time your mind is focused and clear. This means that you are able to do your work. That you are able to concentrate and complete tasks.

CHECKPOINT 3: Your emotional well-being.
Relationships crumble for many reasons, and when a relationship doesn’t work out it is emotional on many levels. When you come back into the dating world world as a single person, you’re coming with more baggage. I’m not talking about baggage from your childhood, none of us escapes that. The baggage I want to work with now is the baggage we get from our long term relationship that has now ended, either abruptly or slowly. (P.S. It never really happens abruptly, we just weren’t paying attention.)

Re-pack your baggage. Take your time. Feel the emotions, acknowledge them, and let them fade. Don’t ignore or squelch them, they will come out in other ways.

Look at your moods and your level of peacefulness and your self-esteem. If you are really depressed you need to address it. If you have a lot of anxiety and fear you need to deal with these emotions, they are natural and normal. You may need to consult a therapist for a time. You may need to look into medication for a period of time. If you don’t sleep well and you don’t have an appetite these are signs of a chemical depression. There are other symptoms of depression and if you aren’t able to do the things you need and want to do, then get evaluated.

CHECKPOINT 4: Your physical well-being.
Are you eating healthy? Are you exercising, playing sports, being active? You need to keep up on yourself physically. This is so important for a number of reasons. The first being that physical activity helps with anxiety and depression. Another important aspect is feeling good about the way you look! It doesn’t mean you need to look like a model or a 20 year old, but you want to be realistic and look the best you can. We all know that part of being confident is feeling healthy and good in our own skin.

CHECKPOINT 5: Re-set your expectations.
No matter how you meet someone, the most important thing is your attitude and your expectations. The good news is, you control both of those. Research shows that the happiest people have NO EXPECTATIONS! You read that right! No expectations. This doesn’t mean that you settle and expect the worst. That would be an expectation. Don’t expect to meet the perfect person on your first date. Do not date to mate. You are out there to meet people. You want to expand your horizons. That’s it.


  • Are you sleeping and eating OK? Are you functioning day to day at your job and in your life?
  • Have you made some new friends? Are you going out and having fun on a regular basis?
  • Is the conversation in your head a positive one?
  • Have you acknowledged your negative emotions and let them fade?
  • Are you physically active and comfortable in your own skin?
  • Have you re-set your expectations?


OK, NOW (and only now) you’re ready to date. Start networking. Let everyone you know that you are interested. Friends, family, co-workers, anyone that knows you! (Internet dating is great too, but comes with its own set of rules, that we will discuss in another post.)

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