Ask Colin: Singledom & Loneliness


Most of my twenties have been spent in a relationship of one kind or another, none of which have lead to fulfillment. For the first time in a long time I have enjoyed being single, though I face occasional bouts of loneliness and wish to find ways to remedy this without jumping into another relationship.

Normally I don’t reach out to people on the internet, but I have been curious about your perspective. What are your thoughts regarding singleness, intentionality in staying single, making the best of your time spent while single, and coping with loneliness which can accompany singleness?

Thank you,


Hey Kate-

Being intentionally single is not for everyone and every situation, but it can be a worthwhile investment of time and energy if you find yourself wanting to change up your rhythm, or if you feel like you’re beginning to lose a bit of yourself in your partnerships.

A little context:

I took two full years off from dating not long ago, and those two years were amazing.

I wasn’t running from dating—it wasn’t a choice borne of a negative experience—but I did want to check in with myself to see who I was without another person in my life. And I wanted to do that assessment purposefully, rather than scrambling to take measurements between relationships, as time allowed.

Those in-between periods, the weeks or months or years we find ourselves going solo because we can’t find the right match, are different from periods in which we decide to not date, and fully commit to that decision.

In my case, I felt like I had been partitioning off space in my life for someone else: keeping it clear for that potential person, even when there was no one there.

When I committed to not dating, though, I started to fill that space, freeing up more of my time, energy, and resources for the things I cared about most.

Even more important in some ways, I was able to figure out what exactly it was that I cared about to begin with.

While in relationships, we tend to do a lot of bending.

There’s nothing wrong with this, as long as it’s not extremely one-sided, and as long as it doesn’t require that we sacrifice something that’s truly important to us; something necessary for us to be happy and fulfilled.

Malleability can help us keep things balanced in our relationships, and it allows us to ensure, as much as possible, that everyone involved gets what they want out of the relationship.

But it’s possible to bend so much, for so long, that you begin to forget what shape you take when you’re not bending at all.

I felt, after all that time, after all that dating (none of which I regret; this is the case with very positive relationships, too), that I didn’t have a clear idea of who I was without another person playing that role in my life. Filling that space with my needs and priorities was part of the process of figuring that out.

Based on my own experiences in this space, and those of people I know who have had similar experiences with intentional singledom, I’m very in favor of being single on purpose—as long as you’re real with yourself about what you hope to achieve, and recognize that it could take a few months to find your new rhythm, and experience some of the benefits.

Being intentionally single is one of the better ways to become and feel more confident and complete unto yourself.

So if and when you do decide to date again, you’ll probably be more aware of your own priorities, know that you can fulfill your own needs—so you don’t have to settle for a relationship that isn’t a good fit—and will be more likely to seek out and appeal to a partner who, like you, is already complete.

Neither one of you will need anyone else to be happy. You both choose to have the other in your life, consciously and happily.

In terms of making use of your time, as I mentioned above, it’s easy to find yourself living according to rhythms that make sense for couples, but not for individuals. Getting past that stage, which can take some time—recalibration usually doesn’t happen overnight—is the first major hurdle. Figuring out what to do with all the time and energy you’ve freed up is the second.

I started a weekly podcast, learned to cook, learned to play the piano and read music, and started taking a variety of online courses. I got into a daily running routine, rededicated myself to my preferred flavor of meditation, took the time to prepare all my meals from scratch, most days, and took long, meandering walks to nowhere in particular, listening to music or podcasts or audiobooks, or just the sounds of my neighborhood.

Your mileage will vary with this, as everyone has different routines and commitments, beyond their relationships. But it’s a near-certainty that you will have more time than you’re used to, once you commit to this idea, and utilizing that time for things you’ve always wanted to do is a good place to start.

Consider making a list of activities, adventures, and skills that you’d like to experience and learn, and start at the top, working your way down, exploring and experimenting and allowing yourself to just enjoy these pursuits for what they are. Enjoy and celebrate growth, take things slow, and do things because you want to do them.

Regarding loneliness when you’re single:

I personally found that my friendships and other types of relationships became even more important to me than usual during those two years, and I reinvested in them, accordingly, just as I reinvested in myself.

It’s possible to devalue such relationships when you’re in a long-term romantic relationship, and you may find, as I did, that you actually spend more time with more people due to the amplified nature and increased importance of these other connections.

If you don’t have relationships that can scale in this sense already, it may be that it’s time to go out and make some new friends, or to expound upon those that already exist, but which remain largely unexplored and underutilized, thus far. Friendships can be some of the most foundational and vital and consistent aspects of a person’s live, if cultivated and invested in. Just be sure to treat them with care and respect, as you would any relationship of any kind that you want to succeed.

One more suggestion is to set up milestones, at which point you’ll check in with yourself and consider dropping back into the dating scene—or at least allowing yourself to consider dating, once more.

I decided to focus on myself, my work and pastimes, and my other relationships, for a year. But at the end of that year, when I checked in with myself about how things were going, I decided to give myself another year; I was just having such a blast, and it made sense for my lifestyle and priorities at the time.

After that second year, though, I decided that it might be interesting to start dating again: to see how I might implement the things I’d learned about myself during that solo period, and to figure out what my next relationship might look like.

I didn’t rush into anything, and it was several months before something I was truly keen to explore popped up on my radar.

But even after I started dating again, I had a far better understanding of what I wanted in a partner, what I needed to be happy, and how I might balance my priorities more sustainably.

Our relationships with other people can be immensely enjoyable and fulfilling and growth-oriented and important, but so can our relationship with ourselves.

Most of us spend so much time on the former, that we can neglect the latter in the trade-off.

But if you have the opportunity and desire to refocus your attention on the latter for a while, and aren’t repelled by the downsides—especially that period of lifestyle recalibration, when you first get started—the benefits can be immense.

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