My date asked me to post his bail and get him out of jail

• My date called me hours before we were supposed to go out asking for a favor. 
• He told me he was in jail and needed someone to bail him out. 
• I did, but we didn't end up going on our date. 

My car thermometer read 98℉, but my third date plans with Dan were not looking so hot. I took a breath of soupy air and typed "Ulster County Correctional Facility" into the GPS.

Earlier that day, I was exiting the hair salon when an unknown caller popped up on my phone.

"Hello?" The reception was crackly.

"Hey, Blair. It's Dan." The remorse in his voice was clear.

Dan worked as an executive coach like me, one year divorced, and a great conversationalist. His quarter-sized green eyes were sweet and sad. I hoped he was different from the intriguing, troubled men — the conspiracy theorist, the drunk artist, the newly divorced professor on a coke bender — I'd met in our small Hudson Valley town.

"I might have to cancel our date tonight," he said.

"Oh, OK…" I said, biting my lip.

"I'm in jail."

"What?" I spat.

He needed money to get bailed out

He explained, from a borrowed cellphone, about his many unpaid parking tickets. The town had issued a subpoena he'd never received because he'd moved; ditching court got him in jail. "We could still go out, but I'd have to be bailed out. It's $400 cash," he said.

It took me a second to realize he was asking me to bail him out. His family wasn't in town and there wasn't enough money in his account, he explained, adding that he would pay me back.

I saw red. The date I'd looked forward to for two weeks was turning into a bad Lifetime movie. How could he ask me to bail him out?

And then, I had the sickening realization that I couldn't let someone I know — even if only for a month — stay in jail overnight due to parking tickets.

I bailed him out

For the bailout, I wore a sundress, just in case the process went quickly and his quarter-sized eyes beckoned. But my stomach was in knots about going to jail.

The jail's red brick facade gave way to white cinder block walls. I emptied the contents of my bag into a tub and smiled at the guards while walking through the metal detectors. They didn't smile back. Beneath my blow-dried hair, sweat trickled down my neck.

I sat on a red plastic bench in an oval room with a desk and a big metal door. The late afternoon sun streamed in through escape-proof squat windows high up on the wall. It smelled like a school cafeteria on sloppy Joe day. A Tupperware of reheated lasagna sat on the bail clerk's desk. He handed me a form and a pen. "Relationship to the incarcerated:" I thought for a minute and wrote: Friend.

I handed over the cash, gritting my teeth and silently repeating, "you'll get it back." Other bail posters entered the room with worried faces, pacing before the desk. Soon, Dan's face appeared in the square window of the big metal door. He came out in handcuffs and an orange jumpsuit. The handcuffs I sort of expected, but the jumpsuit was not sexy. It was tight around his tree trunk thighs, thick from biking.

"Thank you," he mouthed.

I offered a tight smile and a nod. The guard instructed me to meet him out back.

Dan, now dressed in a t-shirt, shorts, and cloak of shame, walked toward my car in the early evening light. He stared at the ground. I felt sorry for him. My heart sank then. I knew we wouldn't recover.

After a silent ride to his house, the awkwardness spiked in his driveway. "Thanks again," he said before closing the door.

As I pulled away, I wondered what was the appropriate length of time to wait before calling him — to ask for my money back. Which I did, but not without a fight.