“You look just like my dead husband.”

The first message I ever sent on a dating app offered a pretty good indication of how unprepared I was to re-enter the dating world.

To my credit, the message was honest. To my match’s credit, he handled it well.

“lol, I don’t know how to respond to that,” he wrote, adding both a smiling and frowning emoji for good measure.

“On a lighter note,” he added, “How are you?”

It was a good question. I was just four months out from my husband’s sudden and unexpected death. Jamie collapsed and died while running a half marathon; he was less than a mile from the finish line, where I was waiting for him. If I answered honestly, I would have said I was heartbroken, devastated, and lost. I was desperate for a way to escape my pain, and had convinced myself that dating was the answer.

Jamie and I met in college. We became fast friends, and, after lots of persistence on his part, I eventually agreed to date him. It was the best decision I could have made. We got married at 23, adopted a dog, moved to new houses and states, and supported each other as we pursued various goals and dreams. I imagined us growing old together, not becoming a widow at 31.

I certainly didn’t anticipate re-entering the dating world 11 years after what I thought would be my last first date.

Online dating offered the allure of a respite from grieving. Each light and flirtatious conversation was a fleeting attempt to numb all the dark and difficult emotions that haunted me. But I couldn’t hide from my pain for long. I’d smile my way through a date at night, only to spend the following day crying about how hopeless everything seemed. Sometimes I’d cry with friends, who tried their best to support me, even if they weren’t entirely sure how to do that. More often than not, I’d cry alone.

Things didn’t work out with my dead husband’s doppelgänger. Nor did they last with the guy who got squeamish every time I brought up death. I tried seeing a Jaime, who pronounced his name the same way my Jamie did. That was weird too. I went on dates with a lawyer, a sculptor, and an adjunct professor. I even tried a long-distance romance, with a widower whose wife died just a month before Jamie did. That had promise, but there was ultimately too much sadness between the two of us.

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