IT HAPPENED TO ME: I Flew Across the Country for a Second Date with a Guy I Met Online

The plane was much happier place to be than at home crying about my failed marriage.
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June Grace
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The plane was much happier place to be than at home crying about my failed marriage.

I’m on a plane right now, flying halfway across the country to meet a man for our second date.

Tucked into seat 15A, my thoughts range from doubt to elevation, back to disbelief again. WTF am I even doing?

I’m a newly divorced single mother who was swept off her feet by a tall, handsome charming man I met online. He was in town for only one night on business, so we met for a beer in the city and he flew back home the next day. Except neither of us could forget each other, so here I am, many, many texts later, flying to Denver to see him.

I consider asking the nice pastor seated to my right to pinch me, to make sure I’m not dreaming. Instead, I share my story with him, about how I fell for a guy I just met and wait to see if he starts praying for me. He doesn’t, or at least not that I could tell. He did, however, hand me his business card, “just in case.” An omen?

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Nervous as I further contemplate my fate and play out worst-case scenarios in my head, I close my eyes and practice the deep breathing techniques my divorce therapist taught me. I reflect back on the fluttering of events that got me to this point in my life.

My husband filed for divorce six months ago after a tumultuous period we dubbed “working on our marriage.” I didn’t ask for the divorce, nor did I want it. I learned the hard way that despite our best intentions, we don’t always get the life we plan, but that doesn’t mean we can’t have the life we deserve.

I adjusted my plans, we divided our assets, and agreed on a custody arrangement. I went through the motions of divorce, numb to most of it, and just tried to focus on my career and keeping life stable for my daughter.

Sometimes all it takes to change your life is a single step, some forward momentum. Make the first move and the rest will follow, if you let it. When I closed the door to my past, the capacity to open my heart to another man showed itself in the most unexpected ways, like little signs sent to reassure me I was on the right path.

The designer wedding gown I had listed for sale online years ago and forgot about? Out of the blue, a lovely woman planning a wedding in the islands bought it. My dress got a second chance, and I used the cash from the sale to buy my plane ticket.

An amazing career opportunity came up, and I grabbed it by the horns and ran with it. I reconnected with old friends, made new friends, and on a whim, posted a dating profile online. Why not? I reasoned. I may as well get my feet wet. After all, the last time I actually dated, Gmail didn't even exist. And how else was I supposed to meet men? At PTA meetings?

Instead of getting caught up in self-doubt and questioning whether it was “too soon” to be in a new relationship, I placed faith in the direction my renewed confidence in myself might lead me.

As if dating in real life isn’t complicated enough, enter the myriad subtleties of online dating. Tinder, eHarmony, Match — what’s a single mother to do?

I settled on Match.com, and a few weeks after setting up my profile and sorting through a plethora of messages, “winks,” and “likes,” my inbox dinged with a message that grabbed my attention.

I responded to this mysterious guy, who had asked me for restaurant recommendations, and shortly after, we exchanged numbers. Our flirtatious texts led to a phone call and immediately, I was drawn in by his sexy voice and intrigued by his charm.

Surely this couldn’t be real, finding an incredible match on my first foray into the world of online dating. Only time would tell.

Our first date blew my mind. The emotional connection we shared felt so natural, like we had been friends for ages, except we just met. As we sampled beers, our conversation flowed, and the chemistry between us was palpable.

When he leaned in to kiss me goodnight and his lips touched mine, I felt my world light on fire. It was as though the ground beneath me shifted and I knew my life would never be the same again.

Our kiss didn’t just take my breath away — it ignited my belief that online dating can actually work. Even if it never went any further than that, it was a sure sign of the good things to come, and a much happier place to be than at home crying about my failed marriage.

Fast forward to the present. Here I am. On a plane. Flying half way across the country to go on a date with a man I met online who I could maybe even fall in love with one day. 

We met at the airport, hopped into the rental Audi, had a romantic dinner, and explored the city together hand-in-hand. We stayed up all night talking, shared breakfast the next morning, and then headed back to the airport to fly home, to our separate lives, putting 3,000 miles between us.

Upon returning home, still floating on cloud nine, it took a few months for the reality of our situation hit me. Careers, children, life. That was reality. Ours, yet not shared. 

We had compatibility, a grounding in our values, a shared understanding of the commitment and hard work required to create and sustain a happy relationship. But was it enough, and was it sustainable from a distance?

As fun as it was to be swept off my feet, and as much as I needed that to catapult me into life as a dating mom, I can see now that it’s all it was: a gift to have experienced such a strong connection and passion, and aspects of a loving relationship that I didn’t have in my marriage that I realized I deserved to have in my life.

Once I recognized the purpose this mysterious man played in my life, it was easier to let him go. After all, it was mostly the idea of him that intrigued me, and that initial spark, as we lived too far apart to give it a real try. 

When I think about him now, I smile. I’ll never forget that first kiss and how it ignited the passion inside of me. I know now I won’t settle for less, and I’m grateful for that lesson.

Love can be messy, and I don’t have it all figured out. The truth is, even when I was married with what I thought was the perfect life, I didn’t have it figured out then either. But this experience was an encouraging start, and so much more than I ever expected from — gasp — online dating. It was worth everything to know that. And I’m headed right back to Match to meet “the one."