My previous worst first "I love you" was romantic in nature, with Sarah. I was arriving at her home, and I greeted her with a whispered "Hello, you," as we embraced.
"I love you, too," she replied.
I would describe the ensuing awkwardness, but nothing could be better than the stammering, excruciating conversation you're imagining. Life tip: if the woman with whom you're actually in love mishears you saying you love her, just go with it.
I think I've beaten this, this time with a new friend. She told me she loved me the second time we ever saw one another. I would have thought this awkward, except that I'd already seen her say it to friends, co-workers, random kids, and a potted plant. She's simply fast and loose with the I love yous. I, however, am not. Her half-dozen or so casual I love yous were met with equally casual deflections.
"Yes, I know you think you do."
We have since become close, and when life recently kicked her ass, I pitched in. Shortly before Christmas, she gave me a present, a home-made video she edited together. She apologized for being broke and thus not able to buy me some dumpster-destined plastic thing that would have meant nothing in comparison. Someone actually put considerable time and thought into making me something? Wow. I couldn't think of anyone ever having done that before. I choked up as she gave me a hug.
"I love you, John," she said. "Merry Christmas."
"I love you, too," I said, and I meant it. "And I don't say that casually," I inexplicably added.
I'd never picked a fight during an embrace before. The violent, angry recoil was a whole-body experience.