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Whether you’re recovering from heartbreak, coping with loss, or have been single for some time, there are a few things worth considering before rejoining the dating scene. While you might be keen to find love or companionship, you may also be asking 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 one, or because friends or family members are encouraging them to open themselves up to romance.
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 affirmation from someone else. Some people arrive at this point more slowly 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 building a relationship with yourself before thinking about letting someone else into your life. In fact, scientists suggest that our relationship with ourselves 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’ll know when the time is right to dip your toes into that giant sea of fish once again. But, if you’re feeling unsure, here are eight questions that’ll 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 at the moment, and consider whether you have the time and energy to give to dating.
If you’re starting a new job, having family problems, or pursuing a dream, ask yourself whether now’s the right time to bring someone new into your life. Sometimes, it can be better to wait until other aspects of your life settle down.
2. What do I want from dating?
Most people who start dating are looking for love and/or companionship. Some people might be on the lookout for their soulmate, while others may be seeking a more casual arrangement.
Whatever you’re looking for, it’s a good idea to be honest with yourself about it. For example, if you want to find someone to spend time with casually, and you’re not looking for anything serious, it’s important to acknowledge this. It’s also best to communicate this to anyone you spend time with romantically to avoid leading them on.
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 we can go through as humans, and most of us do what we can to simply get through it. For some, this can mean diving straight back into the dating scene and a new relationship. But rebound relationships are rarely successful.
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 can be especially true if you’ve just come out of a long-term relationship.
Attempting to mend your broken heart by starting another relationship can often lead to more heartache – not just for you, but for your new partner, too.
The best way to move on from a previous partner and become truly ready to start dating again is to focus on yourself. As with physical wounds, heartbreak can be healed with time, a positive outlook, and self-care.
4. Do I love myself?
Falling in love with yourself doesn’t make you vain or selfish – it makes you indestructible.
Anon
Loving yourself doesn’t mean that you’re vain or narcissistic; it means that you can 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.
For example, are you comfortable being yourself without apologising for it? If not, it could help to work on developing a more positive relationship with yourself before dating again.
People with low self-esteem often feel afraid to express what they truly want from life and, therefore, relationships. They might even find themselves doing things they don’t really want to do or letting go of goals and ambitions to follow their partner’s.
Many people who don’t have much self-love will also accept mistreatment through fear of being rejected and being left 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 who doesn’t treat them in the way that they deserve.
If you think you need to work on boosting your self-esteem before building a relationship with a romantic partner, practise being good to yourself. This can include making time time to exercise, eating healthy meals, or reflecting on something positive about yourself each day.
Our article, 16 ways to improve your confidence and self-esteem, has plenty of ways to practise being kinder to yourself. When you’re able to be yourself unapologetically, you’ll often find new depths in your relationships and feel happier as a result.

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5. What worked well, and not so well, in past relationships?
One way to check if you’re ready to start a new relationship is to spend some time reflecting on past connections. For example, what went well and what didn’t?
Say your previous relationship broke down because you realised that you didn’t have enough in common, or you weren’t communicating effectively. In your next relationship, it’s important to try to avoid these issues.
If you struggled to open up to your partner, it’s worth spending 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 wished you had in common with your partner but didn’t – such as a love of animals, cycling, or literature – it’s best to find these things out about any potential partners early on so you can make sure that you’re as compatible as possible.
Spending time going over past relationships might feel uncomfortable, but it can be beneficial for building an even better connection in future. Try noting down what you’d love a potential relationship to look like. This can help give you more clarity about what you 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 who seems like a great match for you, it’s easy to get swept up in the romance.
While there are few better feelings than falling in love or spending time with someone you really like, it’s a good idea to make sure that you have strong boundaries before you utter that first ‘hello’.
Boundaries are crucial for maintaining a strong sense of self and avoiding accommodating, compromising, or pleasing someone to the point where you don’t remember who you are. Having healthy boundaries generally means not taking responsibility for the actions or emotions of others, which can sometimes be easier said than done.
Examples of clear boundaries to set before you consider going on a first date are…
- Knowing when to say no to something you’re uncomfortable with.
- Respecting your morals and values, and accepting that they might not match everyone else’s.
- Having your own ambitions, goals, and passions.
- Being comfortable in your own company, and having your own hobbies and interests.
- Not giving up things that you love doing for someone you’re dating.
It’s important to establish your personal boundaries before inviting a romantic partner into your life. This will help you feel empowered during the dating process and in the early stages of a new relationship (and beyond).
It can also help prevent you from feeling like you’re at the mercy of someone else and that their happiness or wellbeing is somehow your responsibility, and vice versa.
7. Am I happy?
Before entertaining the idea of looking for love or companionship, consider whether you’re truly happy right now. It’s difficult to build a healthy, fulfilling relationship with someone if you’re unhappy with yourself or your life generally.
Some people believe they’ll 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’ll become dependent on them for it. This places pressure on them and disempowers you, creating an unhealthy dynamic.
Before you start looking for a new partner, happiness should ideally already exist in your life, because, ultimately, the only person who can make you truly happy is you.
The easiest way to take ownership of your happiness is to shift the focus from 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.
Mindfulness is also a great tool for helping you better connect with yourself and develop a deeper appreciation for the little things. If you’d like to find out more about how to get started, check out our introductory guide to mindfulness. Generally, the happier you can be outside of a relationship, the happier you’ll be in one.
For more help with this, check out our article: Are you happy? 10 thought-provoking questions to ask yourself.
Join Rest Less Dating
It’s free to create your profile and browse matches. If you like what you see, get a premium subscription and start contacting like-minded singles near you.
8. Do I feel excited about the idea of dating?
Does the idea of dating give you butterflies, or fill you with dread? If you’d love to have someone to share your life with, but the idea of dating feels negative, it’s best to try to work out why.
If you think it’s just nerves, there are ways around this. Online dating, for example, allows you to have those first exploratory conversations before deciding whether you’d like to meet up in person. Many people find it much easier to let someone down gently online than 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 makes the idea of dating feel uncomfortable or awkward can help you take steps towards resolving it. If you’re really not sure why you’re feeling the way you do, it can help to talk things over with a friend or write things down in a journal.
Many times, people are held back from dating because of fear, which is perfectly normal. If you’re scared about the idea of opening yourself up to love and feeling vulnerable, try to tread carefully and be kind to yourself.
But 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 significant personal growth.
If you’re feeling fear, it can help to acknowledge it for what it is and confront it. Ask yourself questions like: “What’s the worst that could happen?” and “How did I overcome situations like this in the past?” Having an honest conversation with yourself about what scares you can help you let go of your fear, find strength and courage, and choose to look for love.
Final thoughts...
Deciding whether to start dating again is a deeply personal choice, and it isn’t always an easy one. It can encourage you to face up to unclaimed baggage that you’ve been avoiding, and may feel daunting – especially if it’s been a while since you’ve been on a first date.
Therefore, it’s important to take as long as you need to feel comfortable 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 to continue working on and treasuring the relationship that you have with yourself, as that’s the most important relationship of all. Once you do that, everything else should fall into place.
For further reading, head over to our dating section. Here, you’ll find articles like 8 ways to fall in love with your own company and 12 subtle green flags to look for when dating someone new.
Ready to find love?
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 in the comments below.
Elise Christian is Lifestyle Editor at Rest Less. She joined Rest Less in 2018 after achieving a first class Master’s Degree in Journalism from the University of Kent, and writes across a range of lifestyle topics such as mental health, home and garden, and fashion and beauty. Prior to this, she worked as a freelance writer for small businesses and also spent a year training to be a midwife. Elise spends her spare time going to the gym, reading trashy romance novels, and hanging out with loved ones. She also loves animals, and has a fascination with sharks and tornadoes.
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