How to Start Dating Yourself - Michal B. Lehman

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How to Start Dating Yourself – Five steps to help you embark on your journey of dating yourself, and to help you build a stronger self relationship and connection.

Far too often we neglect ourselves and our alone time, mainly in favour of others… But also by not taking advantage of it when we are alone. We dread time alone and see it as a punishment, so whenever we can, we avoid it by spending it with others instead. We show up for other people who need us, but we don’t show up for ourselves. And the time we do have alone, we waste away by either wallowing, or doing things that aren’t productive, and don’t help us utilise it. Instead of using this time to grow closer to ourselves, build a deeper connection and have fun… We spend it in front of the TV or on our phone, and no one ever feels good about spending so much time with screens. The following are the top 5 steps to help you learn how to start dating yourself.

STEP 1 – Prioritise yourself

I understand that life can get very hectic. We get so busy that we just don’t have time for it, and it’s last on our list, so it’s also the first to go. Or in other words, it’s not important enough for us, so we don’t prioritise it. Which is exactly where the self-neglect comes in… We don’t think making time for ourselves is essential, and put others before us, giving them all our extra time. This only puts us down further and shows ourselves that we’re not worthy enough. With this type of mindset, is it any wonder we avoid our own alone time so much?

You also can’t learn how to date yourself if you don’t If we don’t schedule it. change it, we certainly won’t ever be able to see it any differently. This is also why the first step is to start prioritising yourself and your alone time.

Which means, when you build your schedule, you need to make sure to do the following:

Allocate some time for self-dates – When you’re organising your schedule, make sure to prioritise putting yourself in it. Try to do what you can, as often as fits you best. Once a week, two weeks or even once a month is better than nothing. When you get the hang of it more, you can also increase the frequency accordingly.
It shouldn’t be the last thing in, and only if you have extra time – You need to make time for it, because the only way to be worth it, is to show yourself you’re worth it. This can only be done by finding time for self-dates, and not leaving it for the last thing on your agenda.
Don’t cancel on yourself – It shouldn’t be the first thing to be stricken if something comes up, and it certainly shouldn’t happen regularly. Imagine how you would feel if a friend keeps cancelling on you, and you should feel the same towards yourself.
Quality over quantity – As I mentioned above, if all you can do is once a month, it’s better than nothing. It’s also more important that you make it of high value, instead of trying to cram it in every week. Which is why it’s even better sometimes to just do it once a month and be able to invest in it more. Whether it be money, time or effort.

STEP 2 – Make a list of dates

Sometimes the reason we avoid doing something is because it feels too big and scary. We either don’t think we can do it, or we don’t even know where to begin. When we’re lost like that, and feel like it’s just too much for us… We end up doing nothing or avoiding it. Which is likely also why you’re struggling to not only date yourself, but also embrace yourself and singleness. The best method I found to help me start self-dating… Is to take it one step at a time, so it doesn’t feel so intimidating. When you make a list of dates it organises it not only on paper, but also in your head. And it makes it seem and feel more feasible, as well as giving you a great, simple and easy starting point.

Here’s a few pointers to making your list:

Write everything – At this point, you need to write everything down, as long as it’s not a hard no. You can do the filtering later, and also, you never know, you may actually want to try something you’re not sure about now, later down the line.
What do you do with friends? – Think of what you like to do with friends. Then write down all of the options you want to do alone, or are willing to try.
What would you like trying with yourself? – This is also the time to write down any other ideas you’ve had. Or things you’ve been wanting to try. Whether it’s a self-date you wanted to take yourself on. Or maybe just something you’ve been wanting to do, and can try turning it into a self-date.
Search online – look up some self-dates inspo online, either on Pinterest, YouTube, or just a Google search. This will likely give you plenty of ideas to pick and choose from. You can also check out my post – Dating Yourself – 23 Self Dates Ideas
Scale them – Write them down from scariest / most complicated, to the least scary and complicated. Put all of the simplest and easiest dates first, as well as the ones that you’re most ready for. Then work your way up to the end of the list, where you’ll write all of the more intricate dates… Or the ones that you don’t feel ready to try yet.

STEP 3 – Learn to walk before you start running

Take small steps, one at a time, so as to not overwhelm yourself and ease into it better. This way it will also help you stay consistent, because when you jump in head first… Or too deep too soon, you’ll either drown or won’t be able to keep up the pace. What you want to do at this stage is plan out your first self date, and focus just on it for now. You can choose one of the first few “least scariest” ones on your list. For example, if you’re going to start with a home spa-day date, you need to assure you have all of the products you need… And also choose what you want to include on this date. As well as ingredients, if you want to go all out and also make a nice breakfast for yourself to go with it.

Here are a few pointers to focus on at this stage, to help you start dating yourself by taking it slowly:

One date at a time – Take your list, and work your way down it, by choosing one date each time to do. Whatever works best for you at this time, and just focus on the one, until it’s over, and move on to the next. Don’t start planning the next one, before the current one is over… Because you want to be in the moment, and you don’t want to overwhelm yourself.
Focus on “inside dates” – This is especially important if you’re new to self-dating and find going out alone intimidating. To make it easier, and less daunting, start with dates from the comfort of your own home… Where it will be much simpler, but still challenging while not taking you too far out yet.
Examples: spa day, movie night, cooking date, DIY project, or a picnic on your balcony or garden.

STEP 4 – Slowly build your way outside

Once you’re done with your “inside dates”, it’s time to work up to the “outside dates”. Here as well, you want to start small, step by step, and build your way up. If you need to, you can adjust your list to – simple outside dates first, and more intricate, or intimidating ones later. So you can work your way up to them, when you get the hang of it, and feel better about them, and yourself. Learning how to start dating yourself properly requires you to take it one step at a time… But also actually take the bigger, scarier steps down the line. But focus on each one individually to make it easier.

Here are some tips to help to make this transition smoother and easier:

Stay local – Go somewhere nearby, don’t go too far out, and make sure it’s a place you know you feel comfortable in.
Quiet places – Don’t go to places with tons of people, where you may feel not only overwhelmed, but also awkward alone. You’ll focus too much on their eyes and thoughts on you… And not enough on yourself and enjoying your time alone.
Examples: walk and ice cream, picnic at the local park, shopping spree.

STEP 5 – Go all out

Only once you feel ready, you can start working your way further out, to newer places, which will challenge you even more. You don’t have to go all out straight away, but this is the stage to start working towards it more. This will not only help you have a great time with dating yourself, and in your own presence, but also be comfortable alone, more confident and independent. And it will also help you grow thicker skin, and more resilience. You can also adjust your list at this stage, and re-scale the order of the “all out” dates, as you see fit.

Here are a few important pointers for this stage:

Create your hard limits – Going all out doesn’t mean you have to do things that make you feel uncomfortable. Yes it should be challenging, but not traumatic. And if you don’t like something, it’s okay to say no.
A fancy restaurant isn’t a measure – This is just one example, but it’s a classic one, which is why I used it. People tend to use it as a measure of how comfortable you are with yourself, but I don’t think it’s true. First of all, I hate fancy restaurants. Secondly, while there’s nothing wrong with going to one alone… It’s NOT what sets your comfort with yourself. In fact, no one date dictates it.
Examples: Cinema / concert / festival, a day at the zoo or at the museum, a hike or walk in nature.

In conclusion – treat yourself like you would treat your loved ones

Really, you should include yourself within the category of your ‘loved ones’. You’re no less (or more) important than any of them. Learning how to start Dating yourself is one of the most crucial steps in your journey of embracing yourself and your singleness. Think of a relationship you have with a friend or family member… Your connection with them likely deepens and strengthens the more time you spend together, and with every date you go on with them. It’s the same for you with yourself, because it helps you do fun and exciting things alone… Which helps you spend better, quality time with yourself, and also enjoy your alone time. That way you will stop dreading it so much and seeing it as a punishment. And instead, start seeing it as something positive you actually look forward to.