It was on a Monday afternoon. I’d agreed to meet a man with whom I’d been chatting online for decaf tea (I was five weeks into a restrictive 90-day health program, which ruled out meeting for a drink or actual coffee).

I’ve done enough online dating to have a pretty specific philosophy on it:

1. I’ve created a pretty great life for myself and, unless a man brings something similarly great to the table, I’m not interested.
2. Meeting people online allows one an abundance of options, most of whom are not going to be a fit; thus, my objective is to meet lots of people quickly, rule most of them out, and date a few good matches until one emerges as most likely to have relationship potential.
3. I’m rarely nervous about meeting men personally, as I go in with genuine curiosity and an intent to get to know them (even though I know statistically most will not be a match).

So I walked into that coffee shop anticipating I’d be meeting someone I could have a great conversation with but still easily rule out as not a match — and my position seemed to be supported as I spotted a visibly nervous man seated at a table near the window.

“Oh brother,” I thought, quickly assessing that I’d likely have to carry an hour-long conversation for the both of us and wondering how I might minimize the discomfort we were surely about to experience. Ugh. I hoped I might instead be pleasantly surprised.

As I sat down, I noticed everything wrong with him physically: he was too tall for my taste, his front tooth was a little crooked, his features were narrow — not as broad and full as I prefer, his skin appeared red and blotchy, he had a skin tag in almost exactly the spot I’d had one removed months back… And then he led by telling me about a two-week international trip he’d taken during which he’d foraged everything he’d eaten — by choice. Adventurous, yes!… but not my jam.

Our conversation improved as he quickly recovered by sharing how much he liked dining in restaurants and cooking, too. We talked about some of our local favorites, where we’d traveled, children (and step children) and more.

In the end, it was pleasant. And he’d proven to have the emotional intelligence and people skills to build rapport — it wasn’t the one-sided conversation I’d feared it might have been. He asked to see me again and, after a pause to feel into it, I agreed. While I wasn’t sure he was a match, I thought we’d enjoy a dinner together, and it was worth another chance.

That Saturday, I sat in a coffee shop awaiting another first meeting. While I waited, I texted an intuitive friend, sharing that I was meeting someone for coffee then going home to freshen up and meeting Monday’s date for dinner.

“Not feeling your coffee date but your dinner date is a hell yes!” she texted.

“Really?!” I texted back. “I might have thought him a strong maybe at best.”

“Oh, you’ll see,” she replied.

I found myself growing excited as I dressed for dinner. I walked into the restaurant to find my date looking nearly as nervous as the first time we’d met. His energy quickly shifted as we decided what to order, and found ourselves easily talking and laughing for the next three and a half hours until we noticed staff turning chairs upside down onto tables and realized that was our cue to leave. He walked me to my car. I remember that, even though it was slippery, I stubbornly resisted taking his arm (perhaps because he was on the building side of the street and I was closer to traffic and I am a stickler for manners). And then he leaned down to kiss me, twice, in the sort of way that was neither too aggressive nor too chaste, stirring something inside of me and leaving me wanting more.

The next day he texted, “When can I see you again?”

I told him my week was unusually filled with evening commitments and Monday was my only availability… which presented a problem: Monday was Valentine’s Day and surely a reservation would be impossible to come by… except he was friends with a restauranteur and managed to get us a table at a desirable establishment at a moment’s notice.

Again, we talked and laughed and flirted awkwardly… because now that I had started to feel something, I was nervous, just as he’d begun to feel more comfortable. Dear readers, I’m not too proud to say I grilled him, and he answered my many questions openly. When I asked him, “What’s the one thing you most don’t want me to know about you?”, he replied, “Nothing; I want you to know everything about me.” His transparency was astonishing to me yet, curiously, he didn’t reciprocate with similar questions of me.

Before we knew it, four hours had passed… during which time we’d talked, laughed, eaten dinner, held hands and even kissed across the table and then moved to sit side by side, holding hands as we listened to a jazz trio.

I had taken a ride share to the restaurant and accepted his offer to drive me home. By now, I’d grown willing to let him in — trust him to get me home safely, let him know where I lived, kiss him deeply and with desire, plan to see him again and anticipate it might lead to exclusivity.

Today marks two months since we met — two months of:

• engaging conversations, fun and laughing until our cheeks hurt,
• sharing more freely and intimately than ever before,
• trusting in this thing developing between us even when it’s terrifying,
• practicing staying vulnerable and feeling the safety in that,
• joking about our different attachment styles and my skittishness,
• spending more time in bed together than probable for two people our age,
• and wondering how it took so many years, such a remarkable alignment of circumstances, and an incredible leap of faith to find something that feels so easy, natural and right.

I’m struck by how much I’ve had to grow and change to be the person I am in this relationship — how uncomfortable I must allow myself to be to share in this intimacy; how brave, how open, how vulnerable to venture, eyes wide open, into something that feels both like a risk, and so worth it at once.

And to think I nearly let myself sabotage it!