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 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 marriage 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.

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 you overcome situations like this in the past? Having an honest conversation with fear can help you to let go, 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.

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16 thoughts on “8 questions to help you decide whether you’re ready to date again

  1. Avatar
    Kate on Reply

    What a brilliant article. I can identify with so many of these points. From either being, or being with the person who is ‘not ready’. No.4 is particularly close to my heart. Thanks for such a great summary ❤️

  2. Avatar
    Gill on Reply

    Thank you for this, it made me realise I am a long way from being able to think about starting a new relationship. It’s time to focus on me.

  3. Avatar
    Lesley on Reply

    I would love to start dating again. It’s been nearly 6 years since my marriage ended, after a long marriage. I have been asked out on dates in the 1st 3 yrs after my marriage ended. I’m v happy to date now but I’m losing my confidence everyday and I’m saying it’s because I’m busy with xyz but I’m not it’s because I’m scared as I’ve not been on a date since before I got married. Any suggestions would be helpful.

    1. Avatar
      Helen on Reply

      Hi Lesley. Starting to date again can feel like a big step, partly because of all the expectations we can attach to the experience. Maybe start with the mindset of getting out and making some new friends (male or female). It takes some of the pressure out of the situation as there are no grand expectations that this person could be your next ‘one’. From there, you’ll remember that you have lost to offer in all sorts of different relationships, building your confidence towards dating (and you never know – that new friend may just be the ‘one’ anyway!)

  4. Avatar
    Maggie Russell on Reply

    Thank you. I find this site incredibly helpful. I’ve been mourning a lost relationship since 2002 and you have suggested ways to begin to finally recover.

    1. Avatar
      Fiona on Reply

      I have done exactly the same thanks for your comment I feel so much better knowing I’m not the only one to mourn for such a long time. Thankyou 😊

  5. Avatar
    Jane on Reply

    I lost my husband nearly 5 years ago, to a rare form of cancer. It was both our second marriage, we had been together 12 years and married for nearly 6 years. Michael lost his first wife to cancer and I was divorced. When we found each other we both felt like we had finally found that missing jigsaw piece and that we were, now complete. Until I met Michael, I truly didn’t know what is was to be loved, just for me, warts and all…he wanted nothing from me but me. His death was devastating to say the least.
    My friends encouraged to try online dating about a year ago, I didn’t want to as it doesn’t feel comfortable but I did it. And oh boy, has it been a rollercoaster! I have learnt not to divulge that I am a widow; the number of scammers that trawl, these sites is shocking. I literally felt like a detective at one point and had to contact the police on discovering that the person, I was communicating with, was not who he said he was.
    I have met a couple of sincere guys though. One who instantly came off the site, after we first met for coffee and believes this is us set for the rest of our lives. The other is completely the opposite and wants to take thing very slowly. Both have the qualities I’m looking for in a partner ….. however…. and here it comes …. now we are getting to know each other better, I don’t know if I want an intimate relationship or a companion…. I am feeling very mixed up inside …. I think I have become accustomed to my ‘single’ life … me, the cat and the dogs….I’m not sure I want someone moving their things into my home…..I know that sounds very superficial but for me this is mine….I don’t feel I want the order of things changed; I don’t think I could cope with that change…
    Apologies for such a long post….guess I needed an outlet and you guys got it🥴

    So I would advise anyone thinking of dating again to read this article and think carefully and deeply about what it they truly want…. I know I want to feel whole again and have that feeling Michael gave me, back ….

    And if you do go on to online dating, enjoy it but if you think something isn’t quite right, then it probably isn’t….and stay well clear….

    I’ll get my coat …..🤣

    1. Avatar
      Eva on Reply

      Hello Jane

      Loved your post, so candid ❤️

      Have you ever heard of the term ‘Living Together, Apart’?

      I hadn’t, but whilst speaking to a Counsellor after a particularly painful break up she asked what I was scared of… (re dating again)

      I pretty much gave her your answer! She didn’t think it was selfish. That’s when she explained her situation to me.

      Basically, she had met a lovely chap in every way but… She didn’t want to move, he didn’t either etc etc

      They had at that point been ‘partners’, but I guess not in the conventional sense, for many years and it clearly worked. They stayed at one another’s homes but neither got offended if they spent time apart, they were monogamous. They food shopped together, went on holiday together. Everything you may do with a ‘partner’ just not permanently in the same space.

      I have a very dear friend who is married, however her and her husband have turned the house into two ‘flats’. They too have a similar arrangement to above, just in the same house. It works for them.

      I feel we attach too much importance to societal pressure and ideals. Do what works for you, so long as it’s safe (legal) and everyone is in agreement.

      There’s no point one if you thinking you’re in a monogamous relationship (me!!) and your partner is (my EX! 🙄😂) just running ‘free rein’.

      [Also, extra marital/relationship affairs rarely end up well for any parties involved. Surely, if your eye is roaming, the kindest thing to do is leave, then look! Saves a lot of heartache.]

      Let’s face it in a world where we are free to choose (pretty much) anything, being kind to another person shouldn’t be that difficult…

      I’m with you on the whole online dating issue. Be very ‘cagey’ until you feel comfy. You find BLOCK and DELETE pretty quickly. Sadly!! It’s certainly an experience.

      Wishing you all the best on your dating ‘adventure’. Good luck ladies/gentlemen remember trust your gut and stay safe.

      PS if you’re a decent guy reading this, I’m not anti-men just sadly we learn from our experiences. But I have no doubt men are equally vulnerable to the advances of scammers on line. Sadly none of us are immune. Maybe you could share your experience with us?

    1. Avatar
      Simon Gates on Reply

      Hi Gloria, I am the same been in a relationship for nearly 24 years. Devastated that we have come to an end. I love travel and holidays, I am an active Freemason, very honest, loving. Would love to have a lovely lady on my arm for ladies nights. Companionship, travel companion, hopefully eventually a soul mate. I live in Ramsgate Kent near the Royal harbour and am separated.

  6. Avatar
    Liz on Reply

    Very good article and I identify so much with many of the comments.After a 30 year marriage which I did not choose to leave, and now being single for 5 years , I have tried dating but I do have a real fear of intimacy with anyone other than my husband, and perhaps also , although I feel a relationship will make me whole, I’ve fought hard to enjoy independence and I also sense that ‘not wanting anything to disrupt the order I’ve achieved’. I just try and enjoy dating as I’ve found most men quite genuine, but I admit to not being optimistic of finding someone I really want to allow in. And then there’s the getting older every year, perhaps the same concern girls or boys in their 30’s feel when they haven’t found ‘the one’

  7. Avatar
    Barbara Bradshaw on Reply

    What a brilliant article and interesting responses. I do online dating and repeatedly am getting guys replying with sexual talk – would bf e refreshing to actually chat about every day things and form a friendship first

  8. Avatar
    Eva on Reply

    Just a suggestion if you are considering online dating…

    Make a WhatsApp/Facebook group with a few of your closest friends. Post in it who, where and when you’re meeting. It’s a good safeguarding idea.

    Plus you could have a code word for if you need a get out clause if things aren’t going well. Trust me there’s no joy in squeeeeezing yourself out of a toilet window in skinny jeans and heels! 😂

    Just don’t forget to tell them when you’re home (or not!)

    Stay safe x

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