8 questions to help you decide whether you’re ready to date again

Whether you’re recovering from heartbreak, coping with loss or have been single for some time, there are a few things to consider before rejoining the dating scene. While you might be keen to find love or companionship, it can help to first ask yourself – am I ready?

It’s not uncommon for someone to jump into a new relationship as a way of coping with the end of a previous relationship, to escape loneliness, or because friends or family members are encouraging them to open themselves up to the idea of romance again. Generally speaking, the best time to start dating is when you feel confident and happy in your own skin, and when you aren’t seeking the affirmation of someone else. Some people arrive at this point more quickly than others, which is perfectly okay. Everyone has their own timeline, and love isn’t something that should be rushed.

It’s important to remember that there’s nothing wrong with spending some time looking after, and building a relationship with yourself before thinking about letting someone else into your life. In fact, scientists suggest that it’s our relationship with ourselves that lays the foundations for all other interactions – and that self-love could be the secret to a healthy, fulfilling relationship with a significant other.

Only you will know when the time is right to start dipping your toes into that giant sea of fish once again. But, if you’re feeling unsure, here are 8 questions that will help you consider whether you’re ready.

1. Am I ready?

It might sound obvious, but the first question you should ask yourself before you delve any deeper, is ‘Am I ready to date?’ Think about your life as it is at the moment, and consider whether you have the time and energy to give to dating. If you’re just starting a new job, having family problems, or you’re in pursuit of a dream, then ask yourself whether now is the right time to bring someone new into your life. It can sometimes be better to wait until other aspects of your life settle down.

2. What do I want to gain from dating?

The majority of people who start dating are looking for either love or companionship. Some people might be on the lookout for their soulmate, whilst others might be looking for a more casual arrangement. Whatever you’re looking for, it’s a good idea to be honest with yourself – and later on with your date – about this. For example, if you want to find someone to spend time with on a casual basis, and you’re really not looking for anything serious, then it’s important to acknowledge this, and to make this clear to anyone that you spend time with romantically, if you want to avoid leading them down the garden path.

It’s also worth keeping in mind that even if you aren’t looking to make a long-term commitment to someone – sometimes things happen, feelings grow and before you know it, you’ve fallen in love. So, whether you’re looking for love or not, it’s a good idea to be aware of the possibility that once you start dating, love might find you even if you’re not looking for it.

3. Am I over my previous partner?

Heartbreak is one of the most painful experiences that we go through as humans, and the majority of us do what we can to simply get through it. For some this can mean diving straight back into the dating scene and into a new relationship. But rebound relationships are very rarely a success. This is usually because we need space to breathe after a relationship ends, to work through any baggage that we might otherwise carry into our next partnership. We also need time to reconnect with ourselves, and re-establish who we are outside of our relationship. This is often especially true, if you’ve just come out of a long-term relationship.

Attempting to mend your broken heart by starting another relationship will often lead to more heartache – not just for you, but for your new partner, because no one wants to feel like a rebound. The best way to move on from a previous partner and become truly ready to start dating again is to focus on you. As with physical wounds, heartbreak can be healed with time, a positive outlook and some self-care.

4. Do I love myself?

“Falling in love with yourself doesn’t make you vain or selfish – it makes you indestructible.”


Loving yourself doesn’t mean that you’re vain or narcissistic, it means that you are able to recognise your value and how you deserve to be treated. When you’re contemplating whether you love yourself, consider whether you’re content and at peace with who you are. Are you comfortable being yourself without apologising for it? If not, then it could help to work on developing a more positive relationship with yourself before you start dating again.

Having no or very little love for yourself can be quite damaging when you’re dating new people, because you might find yourself making compromises that are detrimental to your happiness. People with low self-esteem will often feel afraid to express what they truly want from life, and from a relationship – or they might find themselves doing things that they don’t really want to do, or letting go of their own goals and ambitions in order to follow their partner’s. Many people who don’t have self-love will also accept mistreatment through fear of being rejected and being on their own. They might worry that no one else will love or want them – so they go to great lengths to stay with a person that doesn’t treat them in the way that they deserve.

If you think that you need to work on boosting your self-esteem before building a relationship with a romantic partner, then practice being good to yourself. This can include doing things like making time to exercise and eat healthy meals – or reminding yourself of something positive about you first thing every morning. This article on 30 ways to practice self-love and be good to yourself has plenty of ways that you can practice being kinder to yourself. When you’re able to unapologetically be yourself, you will often find new depths in your relationships, and feel much happier as a result.

5. What worked well, and not so well, in past relationships?

If the reason that you want to date new people is because you’re interested in finding a suitable mate, then one way to check if you’re ready to start a new relationship, is to spend some time reflecting on past relationships. What went well, and what didn’t go so well?

If your previous relationship broke down because you realised that you didn’t have enough in common, or you weren’t communicating effectively, then it’s important to make sure that these same issues don’t come into play in your next relationship. If you struggled to open up to your partner, then spend some time thinking about why that was, and how you can work on it. Some people find coaching or counselling to be a helpful tool for this. Or if there were particular things that you wanted to have in common with your partner but didn’t – like a love of animals, cycling or literature – then it’s worth finding these things out about any potential partners early on, so that you can make sure that you’re as compatible as possible.

Spending time going over past relationships might not be something that always feels particularly comfortable, but it can be extremely beneficial in helping you to have an even better relationship in the future. Try noting down on paper what you’d love a potential relationship to look like. This can help to give you greater clarity about what you really want, while determining your non-negotiables.

6. Are my boundaries healthy?

“You are special too, don’t lose yourself.”

Ernest Hemingway

Once you start dating, and you find someone that seems like a great match for you – it’s easy to get swept up in the romance of it all. While there are few better feelings than falling in love or spending time with someone that you really like, it’s a good idea to make sure that you have strong boundaries in place before you utter that first hello.

Boundaries are crucial for maintaining a strong sense of self and not losing yourself in accommodating, compromising or pleasing someone to the point where you don’t remember who you are, what you’re about, or what you stand for. Having healthy boundaries generally means not taking responsibility for the actions or emotions of others, which can sometimes be easier said than done.

An example of some clear boundaries that you can set before you even consider going on that first date are:

  • Knowing when to say “no” to something that you’re uncomfortable with
  • Respecting your own morals and values, and accepting/being comfortable with the idea that they might not match everyone else’s
  • Having your own ambitions, goals and passions
  • Being comfortable with your own company, and having your own things that you do e.g. hobbies, spending time with friends
  • Not giving up things that you love doing for someone you’re dating/in a relationship with

Your own personal boundaries might be different, but it’s important to establish them before you invite a romantic partner into your life. This will help you to feel empowered during the dating process, and in the early stages of a new relationship (and beyond). It can help to prevent you from ultimately feeling like you are at the mercy of someone else and that their happiness or well being is somehow your responsibility, and vice versa.

7. Am I happy?

Before entertaining the idea of looking for love or companionship, consider whether you are truly happy right now. It’s difficult to build a healthy, fulfilling relationship with someone if you’re unhappy with yourself, or with your life generally.

Some people believe that they will finally be happy when they meet that special someone, but in reality, placing the weight of your happiness on a single person usually only means that you will become more dependent on them for it. This places pressure on them and disempowers you, creating an unhealthy relationship. Before you start looking for a new partner, happiness should ideally already exist in your life, because ultimately, no one can make you truly happy but you.

The easiest way to take ownership of your own happiness is to shift the focus of it away from companionship or relationships, and try to appreciate what you currently have as a single person. Consider keeping a gratitude journal where you note down one or two things a day that you’re grateful for. Eventually, you will hopefully find enough things to be happy about in your life already, which will help you avoid looking for it in others. Mindfulness is also a great tool for helping you to better connect with yourself, and develop a greater appreciation for the little things in life. If you want to find out more about how to get started, then check out our introductory guide to mindfulness.

Generally speaking, the happier that you can be outside of a relationship, the happier you will be in one.

8. Do I feel excited about the idea of dating?

Does the idea of dating give you butterflies, or does it fill you with dread? If you’d love to have someone to share your life with but the idea of dating feels negative, then it’s best to try and work out why.

If you think it’s just nerves, then there are ways around this. Online dating, for example, is a great way to have those first few exploratory conversations before deciding whether you want to meet up in person. Many people find it much easier to let someone down gently online than they do in person. Our very own Rest Less dating site could be a helpful place to start where you can meet like minded over 50s. 

Try to be honest with yourself about any other reasons you might be cringing at the idea of getting romantic with someone new. Is it due to confidence? Are you still mourning the loss of a loved one? Do you not really have the time to give to dating? Are you worried about the idea of being intimate with someone for the first time in a while? Exploring what it is that is making the idea of dating feel uncomfortable or awkward can help you to take steps towards resolving it. If you’re really not sure why you’re feeling the way that you do, then it can help to talk things over with a friend, or write things down in a journal. If you’ve become worried about the idea of dating since the start of the pandemic, then you might find it helpful to read our article; 4 tips for dating in the current climate.

Many times, people are held back from dating because of fear, which is also perfectly normal. If you’re scared about the idea of opening yourself up to love again and feeling vulnerable, then tread carefully and be kind to yourself. But try to remember that while keeping your guard up and staying within your comfort zone can feel like a much safer option, stretching yourself to do things that feel slightly uncomfortable can lead to great personal growth. If you’re feeling fear, then it can help to acknowledge it for what it is and confront it. Ask yourself: what’s the worst that could happen? How did I overcome situations like this in the past? Having an honest conversation with yourself about what scares you can help you to let go of your fear, find your strength and courage, and choose love again.

A final note…

Making the decision about whether to start dating again isn’t always easy and is so personal to each and every one of us. It can encourage you to face up to a lot of unclaimed baggage that you’ve been avoiding, and can also feel pretty daunting – especially if it’s been a while since you’ve been on a first date. It’s important to take as long as you need to feel comfortable with the idea of putting yourself out there, and opening yourself up to the idea of finding love or companionship again.

Whether you’re ready to meet someone new or not, the most important thing you can do in the meantime is continue working on and treasuring the relationship that you have with yourself, because that is the most important relationship of all. Once you do that, everything else should fall into place.

Have you recently decided that you’re ready to date again? Or perhaps you’ve realised that the timing isn’t yet right. We’d be interested to hear about your experiences. Email us at [email protected] or leave a comment below.

Rest Less Dating is the new safe and secure place to find singles with similar interests near you. It’s free to sign up and view your matches today.

Links with an * by them are affiliate links which help Rest Less stay free to use as they can result in a payment or benefit to us. You can read more on how we make money here.


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