Dating Yourself: Connecting With the Most Important Person in Your Life

The longest relationship any of us will ever have in our lives is with ourselves. Sadly, it’s not everyone’s best relationship. We often don’t give ourselves the same kind of grace or chances we might give a prospective lover or even a long term partner. Arguably, we don’t put in the effort to keep the relationship strong. And we don’t always enjoy ourselves as much as we should. Given that you are the only person who will be with you from the very start to the hopefully-not-so-bitter end, it’s the relationship most worthy of your time and effort. The essence of that relationship is connection. And a great way to forge and maintain that connection is by dating yourself.

Sounds silly, I know. But think about it. When you start dating someone new, you’re at your most open, vulnerable and curious. If you really like them, you want to know all you can about them and you want them to know and accept you. A new relationship often starts with a honeymoon phase, which is something most of us completely bypass when it comes to the relationship we have with ourselves. Healthy relationships lead to lower rates of anxiety and depression, higher self-esteem, and greater empathy. They can also help to strengthen your immune system and lengthen your life. So rather than brutal self analysis and judgment, what if you start dating yourself, learn how fabulous you are and derive all the benefits of a honeymoon phase and beyond? 

Quality Alone Time

Many of us spend a considerable amount of time alone. A lot of that time is spent scrolling through social media on our phones or watching TV. There’s nothing appealing about alone time when we equate it with scrolling. Scrolling can numb us into loneliness. Aloneness is not loneliness. Remember that. Scheduled, respectful, pleasant aloneness can help reduce feelings of loneliness. If we turn some of our alone time into something special, it can improve our wellbeing and our outlook. We typically seek quality time with friends and family and may go to great lengths to guarantee our time with others is well spent. Don’t we owe it to ourselves to infuse the highest quality into our alone time too?

Quality alone time is not to be confused with time isolating. Many of us isolate when we are sad and for some of us, isolation is habit-forming. I’ve worked from home since March 2020 and I live alone. I spend a great deal of time alone and sometimes find it difficult to emerge and rejoin humanity. Like so many of us, in the aftermath of the pandemic, I’m still adjusting. Being social can be exhausting. Effort is required to get up, get out and interact. Over time I’ve come to realize how much I need my alone time. It’s a critical time to reset, reflect, and renew. Sometimes for days. But this is different from the quality alone time in the nature of a self-date that requires scheduling and planning.

The importance of quality time alone applies to everyone. Dating yourself is not something you should do only if you are not in a romantic relationship or you are not receiving the attention or affection you desire from the relationship you’re in. It’s not something you should do only to help you get over a breakup. It’s a smart thing to do regardless of where you’re at in life or your relationship status.

Take Yourself on a Date

By dating yourself, I literally mean taking yourself out on a date. The planning of an activity, a meal (at home or at a restaurant), or a trip shows commitment to nurturing the relationship that means the most, needs the most, and typically gets the least. The activity in question can be going to a show or a spa or a museum or playing a round of mini golf. It can be almost anything. The only restriction is that it should not involve hours of scrolling on your phone or binge-watching a series. If dating to you means being treated well and exploring the possibility of a connection, then go with that and see where it leads.

Self-dating is a way to connect with your interests and your fun side. It’s also a great way to really engage with your life in a way that will make any visioning you do more meaningful. Changes you want to undertake become more likely because you’ll develop a better understanding of how those changes enable you to live your best life.

Show Yourself a Little Appreciation

As I write this post, I’m well aware that going to dinner is probably the first thing that occurs to most of us when we think of a date and not everyone is comfortable going to a restaurant alone. If you are or want to push outside your comfort zone if you aren’t, then go for it. But don’t limit the possibilities. Get creative. Personally, I love taking myself out to see a show. I am also a big fan of solo travel. These experiences are exciting for me and they make me happy. To seal the deal on my self-dating experience, I buy myself flowers too. Every week.

Dating yourself is not meant to replace connecting with others. Humans are hard wired for connection. We need it. But there’s no reason why connecting with others means you can’t take the time to connect with yourself. When you find yourself alone, for a short stretch or a long one, it feels so much better when you’re comfortable that way and appreciate the company.

A Few Dating Guidelines

  • Scheduling a self-date is important. Put your date on the calendar and don’t bail on yourself if a “better” offer comes along.
  • Do it regularly. Make dating yourself a habit.
  • Don’t distract yourself or resort to scrolling on your phone on your date. Quality is key. Mindfulness makes everything better.
  • Don’t be afraid to spoil yourself.
  • Self-dating can get sexy. You know what I mean.

Thinking and Trying

Something to think about: “The most exciting, challenging, and significant relationship of all is the one you have with yourself. And if you can find someone to love the you that you love, well, that’s just fabulous.” — Carrie Bradshaw

Something to try: Obviously I think you should schedule, plan and take yourself out on a date.Extra points if you post a comment to share what you did. But that’s not all. Try listening to the song Flowers by Miley Cyrus, the self-dating anthem. Yes, you can buy yourself flowers! And, finally, if you like podcasts, consider listening to Forrest Hanson and his dad Rick on the Being Well podcast. They’re a helpful delight. Though they don’t specifically address self-dating, they talk about engaging with your life and building stronger and secure relationships.

Coaching Can Help

If you want to start dating (yourself or someone else) and you’re having trouble getting started or connecting, you might consider working with a coach. Let’s jump on a 15-minute discovery call (it’s free!) and see if I’m the right coach for you. Schedule your call here.

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3 Comments

  1. This resonates (as someone who is very tough on himself and often hypercritical of himself). Thanks for the good advice!

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  3. I do not even know how I ended up here but I thought this post was great I dont know who you are but definitely youre going to a famous blogger if you arent already Cheers

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