Dating Yourself,  Embracing Singlehood,  Single Life Blog

Top Self-Dates that Will Help You Feel More Comfortable Alone

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These are the top 15 self-dates that will help you feel more comfortable alone, learn how to enjoy your own company and presence, as well as embrace yourself and your singleness.

More often than not, we neglect the relationship we have with ourselves in order to please others or to maintain one with someone else. And more often than not, we don’t enjoy or even like our own company. We even see it as a punishment, and try to avoid it as much as we can. Whether you’re single or not, developing and maintaining a strong, healthy self-relationship is key to being happy with yourself. And this requires you to actually spend time with yourself… Which isn’t sitting in front of a screen or doing nothing. Especially if you’re single, and want to learn how to feel more comfortable alone and in your own company. Without constantly relying on relationships with others. 

The most effective way to achieve that, in addition to self-caring the sh*t out of yourself… Is by embarking on a journey of self-dating. And yes, I know it sounds silly and awkward, and believe me, I was very shy about it at first too. I didn’t even know where to begin. I was so used to dating others and basing my happiness on every other relationship I had, that I was completely lost. However, with the right blend of patience and perseverance, I managed to overcome my reservations. The following are some self-date ideas that are the best when you struggle with being alone… And want to learn how to enjoy and feel more comfortable in your own company. And no, none of these involves dining alone at a fancy restaurant, because that’s hardly a measure for anything.

What does it mean to like your own company?

Before we dive into the solution… Let’s first understand what it even means, so you know what you’re even looking for. Otherwise, how will you know you’ve achieved it? To enjoy or like your own company, means to enjoy spending time alone with yourself and finding contentment in your own presence. It involves being comfortable and at ease when you are by yourself. Without relying on the presence or validation of others for your happiness or sense of self-worth. Liking your own company is about cultivating a positive relationship with yourself, embracing solitude. And being able to engage in activities, hobbies, and self-reflection without feeling lonely or dependent on external factors for fulfilment. It signifies a healthy level of self-acceptance, self-esteem, and self-sufficiency, where you can truly appreciate your own thoughts, feelings, and experiences.

Here are the 15 self-date ideas to help you feel more comfortable alone and start enjoying your own company:

The following are the best dates for you when you primarily want to learn how to feel more comfortable alone, in your own company. No matter your relationship status… These are great self-dates to help you develop and maintain the capability of being with yourself. Which is super empowering. And none of these includes screens.


Inside solo dates are the perfect place to start, especially if you feel overwhelmed and aren’t used to going out of the house by yourself, and doing things alone. These inside dates will help ease you into the world of self-dating, take it one step at a time, and still challenge yourself, while not going too far out of your comfort zone at one go.

1. Home Spa Day 

This is a date that I formulated during the lockdown because we couldn’t really go anywhere, certainly not actual spas. Yet, I still think that home spas are the best, especially if done right. You’re getting out of your comfort zone, without actually getting out… Which makes this date perfect for starting to learn how to date yourself. I try to treat myself to a home spa day date every month or so. And mini spa evenings a couple of times a month – with some face masks and pampering time. You can check out my blog post about my home spa day date for all the details. 

2. Arts & crafts / DIY projects

This is definitely one of my favourite dates to take myself on, and also do with others. I’m a huge fan of anything creative. A while back, I used old Nespresso capsules to decorate an Ikea lamp I had at home, and that was so much fun. It’s also a great example of how you don’t have to go far and use what you already have at home. And even recycle some stuff.  I have also ordered myself a makers crate subscription box… Which is a great option if you don’t have any ideas or the supplies you need. This is a perfect self-date for spending quality alone time, learning new skills and discovering new hobbies. You can also check out my blog post about my arts & crafts self-date for all the details.

3. Home-cooked dinner date

Personally, I love to cook, and I think both cooking and eating it cosily afterwards, is a great date to have with yourself. Not only are you maintaining a hobby or developing a new skill, but you’re also spending some quality time with yourself. Cooking for yourself is also a great way to take care of yourself… As you’re not only feeding yourself (which is a basic, fundamental human instinct – to feed the ones we love).  You’re also more in control of what you put in your body.

Usually, I like to choose a nice recipe, or watch a YouTuber cook and put my own spin on it. I also put some music or an audiobook in the background so it’s not too quiet. During my regular cooking sessions, I also put on a show, but not on my self-date cooking. You can also check out my blog post about my home-cooked dinner date for all the details.


In order of “difficulty”, every one of these outside solo dates is a progressive step out of your comfort zone, and each one of them is a step further than the one before. These self-dates offer a transformative journey, encouraging us to confront our fears, discover hidden strengths, and cultivate resilience. 

4. Stroll & Ice-cream Self Date

This may seem ordinary, and maybe even silly, but it’s also super important. This is also good to learn how to just take an enjoyable stroll… Without being in a hurry or rushing somewhere. Which is something I always struggle with. It’s also a great way to spend some quality, quiet time with yourself. Strolling around, allowing your brain to wander and your eyes to soak in the local stores, people and colours. Maybe even stop to pick up a nice ice cream on the way.

This self-date also gets you out of the house without feeling too awkward about it. Because you’re not going all out. So it eases you into it. I also think it’s a great way to show yourself that more often than not, small and simple is all you need. And it makes the biggest impact. You can check out my blog post about Stroll & Ice-cream Self Date for all the details.

5. Explore the local markets

Personally, I love going to the local market. When I lived closer, I even used to do my weekly shopping there. Besides all of the amazing aromas, colours and things going on, it’s fun and exciting. Perhaps you can even go on a tasting tour, where you could also meet other people to hang out with. I also enjoy just walking around and getting lost through the different venues and alleys. It’s also not too out there, as it’s usually impossible to tell who’s alone. There’s also so much to do and see, that people will hardly have any more capacity to notice you out and about alone. 

6. A solo-picnic

Taking yourself on a solo picnic date is actually quite good for learning to be more comfortable in your own company, mind and thoughts. It’s also great to learn how to stop caring about what others think, especially about you being out alone. You don’t have to go somewhere packed with people, and you can find a secluded spot for yourself. This helps you get out of the house alone, without doing something too over the top and going too far out. Which is also a great starting date for learning how to date yourself. So grab your favourite book and snacks, and head to your favourite park or spot. You can check out my blog post about my solo-picnic date for all the details. 

7. Day at the beach/swimming pool

The hotel I used to work at was on the beach… And I Loved going after night shifts when it was still early, quiet, pretty empty and not too hot. I would leave my phone at work and just go lay calmly, relieving all of the stress and just truly letting go of everything. Besides that… I think it’s also a great date to go on with yourself, make a day out of it and even combine it with a nice picnic. This requires of you a bit more courage, as it’s harder to hide, and fewer people go alone. It’s also a bit more ‘out there’. But that’s also why it’s a great way to learn how to be more comfortable alone. 

8. Museums/art galleries

Now, I know this is not for everyone, and that’s okay. But even if it’s not your usual cup of tea, perhaps you can give it a try anyway. It may surprise you with how much you enjoy it. I just feel that museums and galleries are a great way to spend some quality time with yourself and learn some new things. Try some new things and experiences. Usually, there’s also a variety to choose from. You can check out my blog post about my Day at the Museum for all the details.

9. Day at the zoo/aquarium

Zoos are primarily targeted towards kids and families, so this one can really test your comfort levels. It’s also one of the self-dates that can help you feel more comfortable alone the most. I have always loved a simple day at the zoo, walking around and visiting all of the animals. Ad maybe even having a picnic. So pick yourself up a map of the local zoo or aquarium, and navigate your way around. For me, the navigation part is also part of the fun. I also love to take the train ride around the park… Which is a great way to practice feeling comfortable and stop caring what others may think when they see you alone. You can check out my blog post about my Day at the Zoo for all the details.

10. Guided tour

Almost every major city around the world has a free tour, where you just tip the guide at the end. So if your city or a nearby city has one, or even a paid one – perhaps you can give it a go. It can be interesting, cultural and a great way to both spend time with yourself and meet new people. It doesn’t have to be a city tour, it can also be a guided trip to an interesting landmark or place. It’s the perfect date to transition from the simple dates outside to the more complex ones… As you’re on your own, but not really alone and it’s harder to tell that you’re there by yourself. You can check out my blog post about my Guided Tour for all the details.

11. Workshops and classes

I’m a huge fan of interactive and creative dates… Where you’re not just sitting around but also creating something new and developing/maintaining your skills. There are so many options and you can do some quick searches on Google to find something near you, that you would enjoy. It can be cooking or baking. Painting, writing or pottery. Cocktail making, sewing, knitting, woodwork, writing or poetry. Or anything else you can find and enjoy. This one is more for the ‘pro’ self-daters. After you’ve had some time to really ease yourself to the outside and more complex self-dates. As here you’re way more likely to be noticed on your own and have to be more resilient to feel comfortable alone. However, it probably has the best payoffs, plus you get to meet awesome new people, with shared interests.


There’s nothing more exhilarating and liberating, than going on an adventure with yourself, and you don’t even have to go all out or far to do so. As you embark on these adventures, you gradually become more comfortable with discomfort, embracing the unknown and thriving in the face of it.

12. Hop on a train or bus

This is another one of my favourites. I’m all for being adventurous and spontaneous… Especially when you’re single and trying to feel more comfortable alone and in your own company. And even more so if you’re struggling to embrace yourself and your singleness. This may take a bit more out of you, but you can also just go with the flow. You can make a game out of it and either toss dice or ask IG stories about where you should go and what you should do next. Let go of all nagging thoughts and worries for a bit, and go with your own flow. Sometimes it’s good to just go, without a specific destination or timeframe in mind.

13. Hiking day trip/walk in nature

I love nature, and I truly believe in its power to help us connect with ourselves. If possible, try to take a trip to the local forest, hiking trail or any other nature park you may have nearby, where you can spend half a day (or even the whole day). Find a nice viewpoint, a peaceful spot to sit and write or draw or anything else you like. You can also pick a spot for a nice picnic. You don’t have to go all out and put on all your best hiking gear, you can even just find the simplest trail, and just walk through nature.

14. Go to a concert/ theatre play/ local festivals

Any of these three are actually fairly good events to start you off with self-dating because they are filled with so much excitement and distractions – that the fact that you’re alone, is likely to go unnoticed, thus removing extra pressure and tension you may be feeling. Also, they’re fun, uplifting and a great way just to let go and disconnect for an hour and a half or so. That said, I would take my time to build up to this one, as it can also be quite daunting to be alone in such a packed, huge space.

15. Explore your city – or a town nearby

We all enjoy feeling like a tourist sometimes. Even if you can’t afford to travel or can’t take time off work, you can simply spend a few hours exploring your town/city through different eyes. Where you usually rush to work or school, you can take your time and explore the streets – you’d be amazed at how much you’ve missed and will be surprised to discover in “familiar” places. You can also head off to a different town nearby if you prefer, and be a tourist there. I like to just get lost, put away my maps app (and my phone in general), and just go where my feet and heart desire. Again, exploring with no destination can be very liberating. Especially when you don’t have to be there at a specific time.

In conclusion – date yourself like you would date other people in your life you feel comfortable with

We dedicate a huge chunk of our time and energy to nurturing and nourishing every other relationship in our lives… That we often forget and neglect the most crucial one – the relationship we have with ourselves. Which should come first and foremost.

We go out on dates, hang out and embark on fun adventures with others, yet rarely, if ever, with ourselves. We feel super comfortable being in the presence of others (or at least we think we do), but struggle to find the same levels of comfort in our own presence. Which is absurd on so many levels. All of these self-dates are not only the best way to grow closer to yourself and create a strong self-connection and relationship, but they’re also a great way to feel more comfortable alone. As well as being alone outside in the world, and giving no f*cks who sees you or what they think about it.

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Stay safe, stay healthy and stay strong!
Michal B.L.

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Hey there! My name is Michal, I was born and raised in Israel, currently I live in a small city near Jerusalem. I'm a certified life coach, and in my Single Life Blog, I write about single life in all its glory and share Single Life Lessons to help you embrace yourself and your singlehood. I offer tips and advice for a better, happy single life, how to be independent, feel comfortable in your own skin and company, and how to not chase toxic people - all of which are based on my own 7-year single life experience.