His eyes bored into her for a painfully long moment.

She pondered silently for what seemed a painfully long time.

The 1970's saw yet another rehearsal of fundamentals in this painfully long analysis.

It took him a painfully long time to register these observations, and to consider the significance of each in turn.

After what seemed like a painfully long moment, he asked, "And you?"

After a painfully long minute, he came up again.

He had to keep himself under control or this was going to be one painfully long trip.

After a few painfully long seconds, Nick opened his eyes.

After the painfully long day before, she'd thought she would have slept like the dead but perhaps the analogy was too apt.

It seemed a painfully long moment before the doctor reached out and took the proffered hand.