I remember what I wrote in my journal when I realized I’d missed my chance to ask her out.

You are an idiot, you are a coward, you are a fool.

The missive was scrawled in barely legible handwriting, my chest tight with inbound anger and pain. I’d come to the café each day for weeks, only to find myself incapable of asking the waitress I liked if she’d go for a drink with me. In the end, her colleague handed me a scribbled number, saying she’d left it for me. It was a lie, but the number was real. I dated the waitress for two years. God bless the colleague.

Left: The writer, looking pensive and thoughtful in Estonia. Right: The writer, looking pensive and thoughtful in Estonia, again.

It seems halcyon and innocent now to have met someone in person instead of via the digital morass of online dating. I first tried dating apps in early 2016. Scarred by the loss of a relationship I’d dreamed would never be lost, I nudged myself toward the burgeoning digital romance scene with reluctance, cynicism, and not even the slightest hint of abject defeat.

Fear of rejection stifled me often; words failed me almost always.

I believed the woman I’d lost was the only person who understood me, with my myriad quirks, troubles, and flaws, and soon came to believe the wave of matches which proved unforthcoming was likely a sign of my unmatchability.I was no big fan of the apps—the cold, random swiping; the conversations with strangers; how the format forces us to judge first (and often foremost) on looks and three or four lines of carefully marketed personality. I disliked the ghosting and awkwardness of meeting people you hadn’t before in places usually visited with friends. I wasn’t enamored when the matches didn’t happen. And though it didn’t affect me, I was aware the apps carried a darker side: the verbal, emotional, and visual abuse experienced by women.

The writer, pushing his luck in Estonia.

For a man with only a side order of confidence and a teaspoon of self esteem, dating apps should be — and often are — a recipe for disaster. But I was never good at speaking to women in person, never good at flirting, of putting my head above the parapet. Fear of rejection stifled me often; words failed me almost always. As time passed, I learned to avert my eyes and stare at my feet, disengaging from the dating world entirely, convinced the modern method wasn’t for me.

But through it all I came to see dating apps as an opportunity; stepping-stones for the meek of us, first ports of call for wallflowers like me, who learned to live with eyes on the ground when we’d rather wear hearts on our sleeves.

As a man with piss-poor to nonexistent self-esteem, apps are a way to tiptoe back into the dating world after the crushing experience of loss

There was no eureka moment in my muddling forays into online dating. Indeed, Tinder continued to pair me with people I didn’t suit and who didn’t suit me. Happn didn’t live up to the description in its name. and as for Bumble… let’s just say it left me stung. In time, I came to realize this was the world now: romance in LCD form; a confused, head-scratching sea of open-ended questions and frequent disappointment. This was romance. It was better to keep going.

The writer, having been advised a photo with Jason Derulo would look good on Tinder.

So I discarded the myth of unmatchability, remembered how easily one could read into the vast silence of digital space and believe each swipe right would inevitably be seen and met with a dismissive left, to conclude that a date that went badly was a date failed. Dating apps are a negotiation of ghosting and rejection, of mismatches and unmatches and prolonged periods of no matches at all, because, wouldn’t you know it, not everyone is on their phones the same time as you.

As a man with piss-poor to nonexistent self-esteem, apps are a way to tiptoe back into the dating world after the crushing experience of loss, to crack jokes uncracked in person, and to display the wit, intelligence, and character your physical self does not always afford.

For the bruised among us, the confused, often unforgiving world of the dating app is an engagement with life itself, another roll of the dice, a refusal to give in to the limits of one’s brittle self-regard. It’s a way of being a fuller version of yourself that your troubled mind denies you, revealing an inner core that the wider world has, for reasons you don’t fully understand, deemed you must keep locked away. It’s an awkward start, but a start all the same.

I’ll swipe to that.