Shelley J Whitehead

How to know if you are ready to date again

14 December, 2022

A question I get asked a lot in relationship coaching is ‘how will I know when I am ready to date again?’ or ‘How soon is too soon to start dating again, after a breakup’. 

I’m a strong advocate of a conscious approach to all aspects of your emotional life and dating is no exception… I believe that clarity gives you the power to make healthy decisions that work for you. 

I’m going to take you through 5 very important things to know before you go back into the dating world, particularly after a painful breakup. 

Dating is a subject I talk about a lot with my coachees. As a specialist in the area of heartbreak, people often come to me when they are either stuck in the depths of their grief or they are coming out of a painful relationship and want to make full sense of the past, so that they make sure they don’t repeat the same mistakes again. Everyone is looking for healthy love and healthy connection… and seeking clarity on how to find that and how to move ahead with confidence. 

It’s important not to be afraid of taking steps forward. And often, after heartbreak, this means dipping your toe back into the dating world. It’s also important not to start dating until you have asked yourself some big questions, to make sure you have established some strong foundations, BEFORE you move ahead. 


  • In the immediate sense, this means that when you hear anything about your ex (or find yourself thinking about them) you don’t go into a complete spiral or decline. Instead, you feel NEUTRAL about them. Wherever there are strong feelings (in any shape or form, including both love and anger) you know there is work still to do, to get these wounds healed, before you can begging to move into a new relationship. 
  • It is also helpful to have clarity about what has happened in  past relationships. Ideally, you would have no major confusions or niggling doubts about what happened or where your major triggers are. I am not saying that you have to have everything healed and everything fully buttoned down – I am saying that you have to have the clarity of SELF AWARENESS. With self awareness, you are not feeling your way in the dark, with no sense of the direction – instead you are moving forwards with an awareness of the pitfalls you need to watch out for. 


  • One of the most important things in relationships is compatibility. You can’t rely on chemistry for a good relationship. If you want something long-lasting you also need compatibility. And, in order to know if someone is compatible with you, you first of course need to know who you really are. What I mean by this is: knowing what your values are, knowing what you really like to spend your time doing, knowing what is important to you… basically, really understanding your own needs. Having clarity on all of these things sets you up to make ‘eyes wide open’ decisions, rather than getting swept away by a feeling that might be wonderful  in-the-moment but in the long term isn’t enough to carry you through into a sustainable and healthy partnership. 


  • If you are in touch with your values and your needs, hopefully you are living a life that is fulfilling those needs and is in alignment with who you really are. If this isn’t the case, it’s a bad idea to enter into the dating process or into a relationship, as you might find yourself looking to others to fulfil your needs. That’s not a great starting place for a relationship. 
  • If, however, you go out into the dating world when your basic needs are fulfilled and you are actually feeling good your life, you will be dating from a place of open-hearted curiosity and joy rather than from a place of feeling bad about yourself. Dating when you are feeling bad about yourself is a sure fire way to attract the wrong partner. If someone is drawn to you when you are not being your true self and aren’t feeling good about yourself, you have to question what it is they are attracted to. Sometimes people can see through to your potential. More often than not, if someone is looking at your ‘potential’ rather than at the reality of you (as you are, today), they are either looking for a ‘project’ or they are seeking a weak, submissive partner rather than looking for a vibrant, equal partner. 


  • Good relationship skills start with good boundaries. That means that you take responsibility for your own thoughts, feelings and actions and don’t take responsibility for the thoughts, feelings and actions of others. With good boundaries, you won’t have any attachment to how dates will perceive or judge you – instead, you are going out to see who you might be compatible with and see how you feel around them.
  • There are many other relationship skills that are critically important in the long term, for relationships (for example, the skill of being able to communicate your needs and consider the needs of others, keeping a good balance of inter-dependence in the mix). However, whilst most of these skills can be developed and refined over the long term, when you are actually IN a relationship, my  strong advice to you is that you try to gain mastery of boundaries, before dating and before starting new relationships, as this critical skill will set you up for success and for strong discernment in qualifying good relationships. 

And finally…


  • This might sound like the most obvious one but it is actually often one of the hardest things for people to define before they start dating. It is INCREDIBLY helpful to have clarity on what you are looking for, both for the dating process and then for your longer term relationships. 

During dating, for example, what you are looking for might look something like this: 

  • I want to explore the process of getting to know you with the intention of it developing into something serious within the next 6 months. 
  • During these first 6 months I want to be able to properly qualify the relationship, to make sure we are compatible in the areas of X, Y and Z… and share the values of A, B and C. What this looks like for me is D, E and F. 
  • During this time, it is also my expectation that we invest regular time in the process of getting to know each other… and what looks like to me is spending 3 evenings a week together, building up to spending weekends together within 3 months and then having our first holiday together within 6 months. 

This isn’t a prescription and that might not be what you are looking for. It’s just an example of how you can put words down on paper to give structure and clarity to your intention, so that you are entering into dating, keeping in mind what really works for you. In my coaching practice, we do these exercises together and write them out,  working on refining them until they feel like a really solid pathway ahead. You might want to try this exercise for yourself – it can be a very powerful one in getting clarity around what you’d like from a date. There are similar exercises you can do for long term relationships, which I share in some of my course materials and in other articles and videos. 

Shelley J Whitehead
you may also like…
Signs of a relationship in trouble

Signs of a relationship in trouble

Today, I’d like to talk to you about some crucial signs that may indicate a relationship is heading in the wrong direction. If you’re able to identify these warning signs early on, you can work on addressing and resolving issues and on fostering a stronger and more...

read more
12 months of love and healing meditation series

Meditation Series

Sign up for my newsletter and every month I’ll send you a soul-soothing meditation from my ‘12 months of Love & Healing’ series.

Newsletter Opt-in / 12 Month Meditation Series