Dating with Confidence: A Single Mom’s Journey

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Updated: Aug. 8, 2016

Originally Published: Aug. 8, 2016

As a single mother of two, my dating life was practically non-existent. When the chance arose to spend a night at a questionable motel with an incredibly attractive man I had only spoken to on the phone twice, I hurriedly arranged for friends to watch my children, aged 2 and 9. It had been three long years since I had been alone with a man—since I had experienced the intimate moments that come with that kind of connection.

With a supportive crew of friends cheering me on—friends who also texted “Are you alive?” the next morning—I met him, exchanged smiles, and almost leaned in for a kiss. Once we were in our room, my body ignited with desire. What had once felt like a mere vessel for nourishment suddenly became a source of allure. He appreciated my figure, but in an unexpected twist, a spray of breast milk erupted over us both. I laughed it off, but even now, just thinking about it makes my eye twitch.

After my second daughter was born, my libido vanished for over a year. The mere sound of kissing made me feel ill. Then a friend suggested a man who could easily be mistaken for Ryan Gosling’s cousin. I found myself falling for him too quickly, but he was adamant about not wanting a relationship. Disheartened yet determined, I decided to explore dating through OKCupid, setting a goal to learn how to meet and engage with men, and perhaps even rebuild my trust in them.

After a couple of months of awkward encounters and disappointing matches, I found myself retreating into a pit of low self-esteem. I faced rejection multiple times and pursued individuals who were far from ideal. I took a five-month hiatus from dating to concentrate on my freelancing career. I wrote my way out of financial struggles and gained enough stability to enroll my younger daughter in full-time daycare. I even treated myself to a smartphone.

Naturally, I ventured onto Tinder and uncovered a surprising number of single men in Montana. Many posed with the dead animals they had hunted—definitely a left swipe for me. Eventually, I had to engage with some of the matches. To my dismay, about half of them vanished once I casually mentioned being a single mother.

Just six months ago, this would have devastated me. I had approached dating feeling like a burden. Even paying for a babysitter felt like a luxury. I previously saw myself as someone others might only take on out of pity or kindness. However, after the breast milk incident, I didn’t feel embarrassed. He told me I was attractive, and for the first time, I believed him. Yet despite my attraction to him, I wasn’t ready for a serious relationship. I had finally gained the confidence to take my time, explore different connections, and enjoy the dating scene without rushing into anything.

My standards increased significantly. I started viewing myself as someone worth pursuing rather than someone who had to chase after others. I went out with firefighters, lawyers, musicians, and even an adventurous Australian who had cycled around the world for two decades.

I still struggle with when and how to bring up my children. Sometimes I feel like I’m being dishonest when I respond “Great!” to inquiries about my weekend, especially when I’m cleaning up after my child’s sudden bout of illness. In the past, I hesitated to mention my kids, thinking it would scare away potential partners who preferred a “no-kids” lifestyle. But why should single motherhood be a disadvantage?

In reality, single mothers should take pride in our resilience and ability to juggle responsibilities that many would find overwhelming. We know how to create joy on a budget, solve problems swiftly, and remain calm during tantrums—skills that are indispensable in both life and dating.

Moreover, when you’re out with a single mom, remember that she’s making a valuable choice to spend her limited time with you. She could be enjoying a relaxing evening at home or reconnecting with friends, but instead, she’s chosen to be with you.

Dating remains a delightful adventure for me, and I’m cautious about introducing new people to my kids—especially since my 9-year-old has a knack for asking, “Is he going to be my stepdad?” It’s clear that it will take a remarkable man to stick around, and I’m willing to wait. For the first time, I feel deserving of that wait. All single mothers are.

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Summary:

This article explores the journey of a single mother as she navigates the dating world after years of feeling disconnected. It highlights her evolution from feeling like a burden to embracing her identity and self-worth. She shares her experiences of dating, the challenges of being a single mom, and the newfound confidence that allows her to enjoy the dating scene without rushing into serious commitments.