Life Advice



Ask Anna: Mastering the art of being happily single

Anna Pulley, Tribune News Service on

Published in Dating Advice

Dear Anna,

I'm a 28-year-old woman who has recently ended a long-term relationship. Over the past five years, I've gone from one relationship to another, hardly giving myself any time to breathe and truly be on my own. My last relationship ended about three months ago, and for the first time, I'm consciously deciding not to rush into another one.

However, I'm finding this period quite challenging. Most of my friends are in relationships, getting engaged or even starting families, and it's difficult not to feel left behind. I keep hearing that this is the time for self-discovery and personal growth, but I'm not sure where to start or how to embrace being single without feeling lonely or like I'm missing out.

I’ve always identified as part of a pair, and the thought of building a life that’s fulfilling on its own, independent of a romantic partner, is daunting. How do I begin to embrace the single life and see it as an opportunity rather than a setback? — Seeking Solitude and Strength

Dear SSS,

Firstly, it’s important to acknowledge the feelings you're experiencing; they're valid and quite common after the end of significant relationships. Transitioning to single life, especially after back-to-back relationships, can indeed be daunting, crappy and full of FOMO. But! It can also be incredibly rewarding. This time is a unique (and also very common) opportunity for self-discovery, growth and building a fulfilling life that resonates with your individuality.


Let’s nip one thing in the bud before we begin. You will definitely experience feelings of loneliness and envy and sadness. These are normal feelings and you can’t escape them — nor should you, as they are proof of your aliveness! To numb, bury or deny these feelings is to numb, bury and deny your own humanness. So, the point is not to run from “unpleasant” feelings, but to let them happen fully. The more you can do that, the more you’ll (eventually) feel relief and make room for other feelings like joy, curiosity, wonder and whole-heartedness.

TL;DR It’s OK to have days where you feel the loneliness more acutely, but these moments are part of the process of becoming more resilient and self-sufficient.

Start with self-reflection

Now that we’ve addressed that, what else can you do to kick-start your new and wondrous journey in singlehood? You’ve already got a few months under your belt, which is great. Begin by spending some time in self-reflection. Journaling can be a powerful tool for this, helping you to understand what you value and what brings you joy independently of a partner. Reflect on your hobbies, career aspirations and how you want to grow personally. Some prompts to get you started:


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