Falling In Love Again as a Single Mom

During my pregnancy many of my friends remarked, some with more sensitivity than others, on the likelihood that I would successfully date again now that I had baggage. Their words, not mine.

I suppose many of them considered their own dysfunctional Tinder journeys and calculated that it was difficult enough dating while “normal,” let alone having some remarkable circumstance attached to you, like a child.

It’s important to remember for context that most of my network was made up of young millennial professionals living in Tier 1 cities. Marriage was something reserved for your mid-thirties and children happened some time after that, after having achieved a certain level of success in your career.

As for myself, dating was the farthest thing from my mind. Perhaps I’d already internalized what they were all suggesting and resigned myself to a Gilmore Girls existence — just me and Olivia taking on the world.

One evening, sometime after Olivia and I had moved back to Virginia, I met up with two of my hometown friends for dinner. These two were amongst my closest friends from high school so they knew about my journey over the past year and were incredibly supportive. It was really the best kind of friendship — there was no judgement among us, we were just there for one another.

These two friends were both guys and both single, so we spent much of dinner swapping hilarious stories of online dates gone wrong that we’d either heard of or experienced ourselves.

Inevitably, the suggestion came around that I create a profile and “get back out there and just have some fun.”

“I don’t know. I think it’s too soon. Olivia won’t even take a bottle, so I can’t be away from her for more than 45 minutes at a time, it would never work. Besides, I don’t even think I’m ready.”

Meanwhile, the hamster wheel in my head was spinning from all the comments I’d heard directly or indirectly about the likelihood of any male wanting to get involved with a single mom.

Somewhat reluctantly, but also with a bit of glee, I pulled out my phone and downloaded a popular app. With input from the guys, I started to craft my bio and select pictures, at which point one of my friends grabbed my phone and selected the pictures for me, all from a single man’s perspective. Surely someone would date me now, I thought sarcastically.

This encouragement to “get back out there” wasn’t just coming from my friends. My dad also kept advising, “you know you can leave her with me and go out on a date or out with your friends?” My mother shared the same.

“And what happens when she starts crying and wants some milk?”

“We’ll figure it out.”

No way. If there was one thing I couldn’t stand, it was the idea of Olivia crying for me and me not being there.

A few days went by and I was sitting up in bed, Olivia sound asleep next to me, when I decided to open the app and just see what happened.

Bleh.

I closed the app and went to bed. This wasn’t for me. I’d just wait until Olivia was off at some precocious high school, then I’d fall in love with the local deli owner.

A few nights later, feeling a little bored sitting in bed next to a sleeping Olivia, I opened the app again.

After a few minutes of swiping left, I came across a gentleman whose photo was strikingly handsome and whose own bio was written in a refreshingly clever way. Even in those few sentences, I could tell he was intelligent.

Well, this is interesting…I swiped right.

Ping!

Our two faces swirled together on the page — a match. Feeling playfully courageous, I sent him a message.

Ping!

A response. I laughed out loud. We continued to text for the next 45 minutes and that night I went to bed giddy. His name was Dustin.

That week was a flurry of constant text messages until one night I decided to call him. I had to know what his voice sounded like. What if he had a voice that sounded like nails on a chalkboard? It wasn’t a detail I wanted to leave to an in-person meeting at this point.

I picked up the phone and called him. I could tell he was surprised, but much to my relief, his voice was smooth and quite sexy.

“Oh, wow!” I exhaled into the phone.

“What?”

“Your voice…it’s just…it’s great.” Oh no, I was already sounding like a crazy person.

“Um, thank you?”

We talked for the next two hours and in that time, fell into an intimacy from which I knew we’d never recover. It occurred to me that some people can achieve an intimacy in minutes that might take others months, or even years, to attain.

We spoke about my unordinary journey to single motherhood, and I could feel the chivalrous, protective instinct in him engaging. For all my stoic feminism, it felt so good to have someone assume the role of male protector. With every comment he made, it was as though he was reaching through the phone to hold me and reset my idea of normal, undoing the ordeal that should have never befallen me.

He then shared his own story, which included a contentious divorce process after more than a decade of marriage. He spoke of an altogether tragic dissolution as my heart sank.

“I’m sorry, but with everything you’ve just shared, it seems to me that it’s too soon for you to be getting seriously involved with anyone. And I understand the desire to date. In fact, I think that’s perfectly appropriate given where you’re at in the process, but I’m not sure that I’m up for anything casual. And I’m sorry because I thought I was, but I realize that I don’t know how to do casual.”

He took a deep breath and responded.

“Look, I’m not dating with any pretense — that this will be casual or serious or otherwise — I’m just taking it as it comes. And I hear what you’re saying about timing. It’s been on my mind too and that’s why I’ve been concerned to tell you all of this.

My family has suggested the same — that it’s too soon. All I can tell you is that this is something I’ve wanted for a long time and now that the band-aid has been ripped off, I feel like Andy Dufresne at the end of Shawshank Redemption…I feel free.”

He went on, “I know there’s still a bit ahead of me as far as this goes, but I only get one life and I don’t want to put life on hold for life.

A smile crept across my face. Here was a man of my own sensibilities. All we have is this moment and I didn’t want to walk away from it either. We made plans to meet for dinner.

The day of our first date rolled around and Dad agreed to watch Olivia. I was beyond nervous and thought about cancelling several times — I’d never been away from Olivia for more than hour. I breastfed her right before I left and headed downtown to a favorite local restaurant.

When I pulled up in front of the restaurant, I saw him sitting on a bench across the street. Upon seeing me, he stood up and I could see that he was tall, much taller than I’d imagined. He was wearing a blue shirt that matched the bluest eyes I’d ever seen. His hair was long, but not shaggy. He looked every bit the Californian.

A smile crept across his face as he walked towards me. He bent down to kiss me on the cheek, then opened the door and escorted me inside the restaurant.

We talked and laughed throughout the entire meal. He wasn’t a bit bothered by the fact that I kept my phone on the table in case Olivia needed me, or that I texted my Dad every 20 minutes to check in on her. Dad responded each time with, she’s doing just fine.

As soon as he paid the bill, I quickly said goodbye and headed to my car — I’d been gone almost two hours and I was struggling. He was gracious, walked me to my car, and kissed me again on my cheek.

“I hope to see you again soon,” he said.

“I’d like that very much.”

I pulled into the driveway and went running into the house. There she sat in her baby Bjorn bouncer, banana puree dripping down her chin and Dad squatted down in front of her with a spoon. My heart was full. I swooped her up and took her downstairs to get ready for bed.

As I sat rocking her, my phone pinged. It was a message from him.

Any man that walked away from you is a damn fool. They’ll never find better. It doesn’t get any better than you. You’re perfect.

For the next month, whenever Dustin didn’t have his children, he’d head to Staunton and stay at local hotels to be close by so that whenever I could find time to peel away, we could meet for coffee, lunch, a drink, or even dinner.

Eventually, Olivia began to join us for our lunch or coffee dates and as we grew more comfortable with one another, Dustin would join us at my father’s home for dinner.

Dustin’s relationship with Olivia was immediately paternal. He was a natural. Simply put, he was a Dad. In those weeks of courtship, he stepped in to tackle some of my most daunting parenting challenges. He taught Olivia to take a bottle and even stayed to help us put her to bed in her crib, something my parents and I had yet to accomplish because neither of us could stomach letting her “cry it out.”

Dustin would often remark how amazing it was just to be dating me and the fact that Olivia was part of the package was “the best bonus.”

One evening as we all sat together watching the sunset from the back porch, I caught him looking over at me and Olivia.

“This is what life is about,” he started.

“What?”

“This. Right here. You and Olivia. You and Olivia are what life is all about. And I still can’t wrap my head around anyone not wanting to be a part of this. But their loss is my gain and I’m the luckiest man on earth.”

The following months of our budding relationship saw many ups and downs as we further introduced our two families, coped with the trauma of his divorce, and both adjusted to new lives in a new place.

Despite the turbulence, what saved us is that as Saint-Exupery once explained, we both continued to look outward together in the same direction.

It’s been more than 2.5 years since we met and today we are now expecting our first child together and our blended family couldn’t be more excited.

So it turns out that with a bit of courage, resilience, and openness, you can indeed fall in love again and if it’s the right person, being a single mom is “the best bonus.”

Interested in reading and writing about personal stories. Opinions and observations are my own.

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