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Ask Anna: Mastering the art of being happily single

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 okay 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:

  • What are three things you love doing that don’t require anyone else?
  • What are your key personal values? How do they shape your daily activities?
  • What long-term goals do you have for yourself? Break down the steps you can start taking today to reach these goals.
  • Describe where you see yourself five years (or one year) from now. What are the key differences from your current life?

Others to check out: MindBodyGreen has 77 therapist-approved prompts; PsychCentral has 64; and Sage and Bloom has 57.

Explore new interests

Without the compromise that often comes with relationships, you’re free to explore new interests or revisit neglected ones. Whether it’s art, sports, learning a new skill, or diving into books, these activities not only enrich your life, give you interesting things to talk about, and can also introduce you to new communities and friends who share your passions.

Here are some excellent resources (many you can partake from the comfort of your couch) that cater to a wide range of interests:

For learning new skills:

Coursera (coursera.org): Offers courses from universities and colleges on a multitude of subjects, including personal development, art, technology, and more. (I highly recommend their Happiness course, which is free and super popular.)

Skillshare (skillshare.com): A learning platform with courses in creative arts, design, photography, writing, and more, taught by industry experts.

MasterClass (masterclass.com): Enables you to learn various skills from celebrities and world-renowned experts in their fields, from cooking with Gordon Ramsay to creative writing with Margaret Atwood.

For art and creativity:

Meetup (meetup.com): Helps you find local groups and events based on specific interests or hobbies, including art workshops, book clubs, and more.

CreativeLive (creativelive.com): Provides live and on-demand classes in photography, art, design, music, and crafts.

For sports and physical activities:

Eventbrite (eventbrite.com): A platform to discover events in your area, many of which are sports-related or fitness workshops, ranging from yoga sessions to hiking groups.

REI Experiences (rei.com/events): Offers outdoor classes and tours, including hiking, cycling, and kayaking, wonderful for those looking to explore nature and meet fellow enthusiasts.

For book lovers:

Book Clubz (bookclubz.com): An online platform that allows you to join or create book clubs, an excellent way to share your love for reading with new friends.

Your local library also has book clubs—and tons of opportunities to meet and connect.

Or, ask a friend (or three) if they want to start a book club. No need to overcomplicate this. I started a monthly, very informal “club” with one friend and it’s been wonderful.

For personal growth:

TED Talks (ted.com): Offers insightful and inspiring talks on a myriad of topics, from science and business to personal growth and creativity.

DailyOm (dailyom.com): Provides courses and articles on personal growth, spiritual well-being, and physical health.

For making new friends and community building:

Bumble BFF (bumble.com/bff): A module within the Bumble app designed to help you meet new friends in your area.

Nextdoor (nextdoor.com): A neighborhood hub for sharing news and (often) helpful information, goods, and services.

Cultivate relationships

While your friends might be in different life stages, remember that meaningful connections come in many forms. Rekindle old friendships, strengthen family ties, and don’t shy away from making new friends who align with your current journey. (See above for options to do this!) Shared experiences can be found in places you least expect, and they are integral to a fulfilling life.

Solo adventures

Embrace the freedom to pursue adventures solo. Traveling alone, trying out a new restaurant, or going to a movie by yourself allows you to indulge in your preferences and teaches you to enjoy your own company.

For travel, there are tons of options, many geared to women: Solo Traveler (solotravelerworld.com), AdventureWomen (adventurewomen.com), Tourlina (tourlina.com), Solo Female Travel Network (thesolofemaletravelernetwork.com), Intrepid (intrepidtravel.com/us/womens-expeditions), and many more.

Start (or re-up) a self-care routine

Self-care can sometimes be perceived as a luxury reserved for those with the means, but real self-care isn’t an indulgence—it’s building essential habits for promoting your well-being and underscores the importance of dedicating time and effort to your own health and happiness. Whether it involves exercising, meditating, nurturing your skin, or losing yourself in a book, prioritize activities that uplift your spirit and self-esteem. 

Seek support

If you find the transition overwhelming, seeking additional support from a therapist or a support group can provide additional strategies to navigate this phase more comfortably.

Lastly, let me leave you with this thought from Mandy Hale, author of The Single Woman: “Until you get comfortable with being alone, you’ll never know if you’re choosing someone out of love or loneliness.” 

Embracing single life isn’t just about filling your time with activities; it’s about learning to appreciate your own company and understanding that completeness comes from within.

Wishing you strength and joy on your journey of self-discovery.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books!

This column originally appeared on The Chicago Tribune.

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