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How to Start Dating Again After Being Single For a Long Time

by Kimberly Delarosa

Photo by Ava Motive from Pexels

Millennials and Generation Z made the single lifestyle the new norm. Over 50% of people in the U.S., between the ages of 18 and 35 are single. Many people, particularly women, are choosing to live a lifestyle that was non-existent to them 40 years ago. From an oppressive past with limited opportunities, women today can and do live by our standards. For women, being single is a revolutionary act. It’s honoring and embracing the possibilities of what the future can hold.


After having a bad breakup with a guy who was my best friend, it was the first time in my life where I lifted my arms in the air and declared “That’s it - I’m done!” I was tired of trying, tired of failed relationships, and tired of pouring my heart out, only for it to be crushed over and over. So, I went solo for a while.

During that time, I started living for myself and no one else. I had my studio apartment, showcased artwork in galleries, went to yoga, and started going to lunch in restaurants by myself. The thought of being single permanently was looking good. “I could do this,” I remember thinking to myself while sitting in my apartment drinking tea while my cat Nebula purred on my lap.

Then a few years later, I met Will. I was working at a design firm in the city, and he worked a block away. The first thing I remember about our initial encounter was his eyes. How I looked into them and felt my heart skip a beat. He looked at me, smiled, and I thought, “Wow, what kind eyes.” That’s when I realized I wanted to date again. But after being single for a while, how do I even begin?


Dating, or courtship if you’re on that Bridgerton vibe, is letting the world know that you’re officially open to love. For single women, however, dating has its polarities. It can be fun and spontaneous, but it can also feel like walking on eggshells. “You might not hit it out of the ballpark on your first time out or even 10th,” says Treva Brandon-Scharf, a dating coach and first-time bride at 51.

Brandon used her years of surviving singledom and wrote about them on her blog called The Late Blooming Bride: “There might be hurt feelings and disappointments along the way, but that’s the nature of it. Dating and finding love takes time, faith, and patience.”

If you’re thinking about dating, it means you’re open to falling in love. Regardless if you want to date just for fun, it’s wise to know this when entering the dating realm. That doesn’t mean you’ll fall in love with the first person you meet. But the fact remains that love is unpredictable. It can appear out of nowhere, and whether we like it or not, it can be out of our control.

I knew I wanted to date again, but I didn’t know how to necessarily go about doing so. I’m one of those introverts who always says the most awkward comment on a date (“So, global warming, huh?”). Naturally, dating feels exciting and new as well as nerve-wracking. However, experts say before you jump the gun, make sure you’ve settled the past.


Fiona Eckersley, life coach, and author, states to “first look at how you feel when the subject of past relationships comes up.” Past relationships, whether good or bad, lay the foundation of what you desire in a partner. Regardless of the mistakes, you’ve made or lessons you’ve learned, past relationships don’t define you. Rather it elevates your awareness to find the best kind of love for you.

Entering with the mindset of a clean slate opens up the possibility of love. However, if there are strong feelings still festering inside, unresolved feelings, it’s something that needs to heal. Unresolved issues from past relationships like trauma can carry over, which makes us unknowingly sabotage our happiness.

At first, this concept is confusing to understand. Rom-com movies and pop culture send messages to singles about the necessity of non-stop dating. Yet healing the past and doing the inner work first is, without a doubt, the wisest choice and what creates a positive result when getting back in the dating world.

Once you’ve let go of the past and fears of the future—which no one can control—you’ll be able to build the confidence to get back out there.


“When you’re ready, all you have to do is think if you’re ready and then put yourself out there,” says Robin Sutherns, relationship expert and editor-in-chief of Galtelligence. “You know you’ve got something to offer.” A huge part of dating is to have the confidence to know that you’re a catch. It requires you to take ownership of who you are. My favorite scene to watch in movies is when the group of girls helps out a friend in need with a full-fledged makeover. It’s a spell happening in person, a ritual of self-confidence and courage. It implies a level of self-confidence and ownership.

Sutherns addresses another issue that most people fail to do: take action. The art of dating has advanced throughout the years in many ways. It no longer requires you to attend a family function and be set up by your parents. With online communities like and EHarmony, meeting new people has become more available than ever.

“Whether it’s online or in real life, always be on the lookout,” states Brandon-Scharf. The internet, while presenting challenges, luckily also makes it easier to stay safe. For instance, you can run a people search to quickly find out if someone has a criminal record, an alias, is secretly married, or is still active on dating apps after they've started seeing you.


Eartha Kitt said it beautifully in her film “All by Myself: the Earth Kitt Story” after laughing hysterically when asked if she would compromise herself for a man: “I love relationships. I think they’re fantastic and wonderful. I think they’re great. I think there’s nothing in the world more beautiful than falling in love…but falling in love for the right reasons.”

After being in a few relationships, I noticed a pattern. Every time I entered into a relationship, I would lose myself. I would commit my entire being to the relationship and forget to make time for myself. My life would be to make sure this relationship went well for fear of being abandoned when in reality, I was abandoning myself in the process.

The whole idea of dating is to find someone to share your moments with, not alter who you are. Eckersley points out that “having a strong sense of who you are and what you want is necessary to break the patterns that may have led you to date people that turned out to be less than ideal.” Find out what you want from your dating experience and be clear on your boundaries.


Always remember the healthiest relationship that you could have is the one with yourself. You are simply sharing your life with someone who you find interesting. No one is perfect - we are all perfectly flawed. But it’s the flaws that shape who we are. It’s the uncomfortable moments that define our future and reminds us just how exciting life can be. How magical love can feel and how it’s the right of our very soul to find love.

I dove in with Will, and we fell in love in the city. A few years later, we’re married and have a son. And I’m happy to report to this day, he still looks at me the same way as the day we met: with those kind eyes. So, take a risk girl. Decided that your worth it, believe you can have it, and open yourself to the possibility of love. You never know what might happen.



The Washington Post - It’s not just you: New data shows more than half of young people in America don’t have a partner.

Fiona Eckersley, life coach and author

Robin Sutherns, dating expert and editor-in-chief of Galtelligence

Eartha Kitt on Love and Compromise

Treva Branson Scharf, life coach and dating expert


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