I was never good at asking women out. No matter how smooth I sounded when I practiced (yes, I practiced – don’t judge me), I never managed a level above not quite painfully awkward. Even though I eventually accepted I just don’t have game, I tried again and again anyway. When you usually get a “no,” you have a lot of opportunities. Once though, I almost pulled off the perfect request. Almost.

The two restaurants I most often ate in while in college were the two Shoney’s in Clarksville. At one of them, a waitress caught and held my attention. She was tall, slender, and the embodiment of Starsha from StarBlazers (the Americanized version of Space Battleship Yamato). I was obviously attracted to her, but the first time I heard her soft, gentle voice I was completely smitten.

“Is she seeing anybody?” I asked one of the other servers I knew.

“Actually, she is. One of the cooks.”

“Oh,” I said, crestfallen.

“But you should ask her out anyway.”

“Wait, what?”

“Ask her out anyway. We’d rather she was with you.”

I didn’t ask her out. I was bad enough at it without adding the pressure of her already seeing someone else to the mix. I did start requesting her section though. She was always pleasant, but didn’t smile much and often glanced back to the kitchen.

One night as I checked out, the hostess leaned over the counter and whispered conspiratorially, “Hey, I thought you’d like to know he broke up with her.”

“Oh,” I replied not understanding at first. Then it dawned on me, “Oh! Uh, wait. What makes you think I’d like to know that?”

“As if we all haven’t seen the way you look at her,” she laughed.

“Really? Everybody?” I was mortified.

“Yep, but if it helps, we’re all rooting for you.”

“Uh, thanks.”

I wish I could say I waited a couple of weeks to ask her out to wait an appropriate amount of time. The truth is I was plain chicken. But I did decide to ask her out and purposed to do so soon.

The next time I went to Shoney’s, I requested her table. It was November and I hid a rose in my jacket. The hostess gave me a knowing smile as I took it out and placed it on the table. I panicked for a moment when the wrong server approached the table. I quickly tried to hide the rose, but she noticed. She also burst out laughing.

“I just came to say good luck,” she told me.

When the correct server came over, I talked to her as normal and didn’t mention the rose. She glanced at it, but also said nothing about it. I ordered my usual and she left. Every time she came back for a refill, her eyes darted to the rose. Her glances lingered longer slightly each time. She was about to hand me the check when she cracked.

“Okay,” she said, “I have to ask. Who’s that for?”

This?” I said as I picked up the rose and held it out to her. “It’s for you.”

“For me?” She seemed quite surprised.

“Yes, for you.”

“Wow.” Then she smiled. The room brightened and I thought I actually had a chance.

It seemed like the right moment so I said, “I really want to ask you out, but I’m kind of afraid to.” Yeah, I know. Lame.

“Why don’t you ask . . . or I could just say yes.”

“Yes?”

“Yes.”

“Yes, meaning, you’ll go out with me.”

“Gladly.”

We made quick plans for me to pick her up after work. Some of the other servers gave me thumbs up while her ex stared daggers at me from the kitchen. I didn’t care. I asked her out somewhat (okay, not at all really) smoothly and she said yes.

You might think my bobbling of the question is what kept it from being the perfect request I always wanted to pull off. Sadly, that wasn’t it. The real issue was that I brought my roommate and his girlfriend along for moral support. There’s nothing wrong in seeking such encouragement from friends, but it’s another matter entirely to actually bring them with you.

At least she said yes. We paid and I smiled stupidly as we exited into the cold night air. I looked forward to our date, never guessing it would be our only one.

© Leighton Brown and Stories Now Told, 2011. Unauthorized use and/or duplication of this material without express and written permission from Leighton Brown is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Leighton Brown and Stories Now Told with appropriate and specific direction to the original content. For more information, please see the Copyright page.