"How many tickets are you buying?" I asked him as I stirred my whiskey sour.
He smiled before turning toward the woman with the roll of tickets. "How many tickets will $50 get me?"
Her eyes widened as she did the math. From what I had noticed, nobody had bought more than $10 in raffle tickets.
Once Scott had a ridiculous hand full of tickets, he stretched his arm out in my direction. I looked at him, confused, before he clarified. "I know you like to win. Hopefully this many tickets does that."
I gave him the cheesiest smile I could manage. "You know me so well," I said as I planted a kiss on his cheek.
He told me he was going to the bathroom, so I took the time to walk around the raffle baskets and strategically place my tickets into the ones I wanted.
I got to the end of the table, where there was a bottle of red wine wrapped and an envelope attached to it. Red wines not really my thing, but I leaned down to read the envelope anyway.
"Don't even think about it, kid," I heard the voice behind me. I turned to face Pete and he was smiling, holding a glass of what looked like scotch.
"What?" I asked with a raised eyebrow. "Do you want this prize?"
"Of course," he replied with a laugh. "It's the only thing worth winning here."
I turned back around and examined the envelope. It was a two night stay at a really nice hotel on the water, with a breakfast and dinner included.
"Well, I hate to break it to you, but I'm winning it," I responded as I dropped four or five tickets in.
Pete shrugged. "If you want to waste your tickets, that's fine with me. I'll have you know I'm very lucky."
"We'll see," I playfully replied to Pete as I continued picking baskets. Shelby found me a few minute later and I was surprised to see how drunk she had become.
"Caroline," she slurred. "This is so much fun!"
I suppressed my urge to laugh. "Yeah, I'm having a good time," I replied with a smile. I had hung out with Shelby a few times outside of the office, but had never seen her get drunk like this. I didn't want to seem judgmental and tell her what to do, but I also hoped she wasn't going to get too drunk and regret it. I asked her if she wanted to hunt down a cocktail waitress with some food.
As I was stuffing a mozzarella stick into my mouth with Shelby, Scott found me. We decided to make our way to the table since they were taking dinner orders.
I sat and drank with Scott and a few other people from my department. It was nice to see everybody out of the office and get to know them a little more. It was even nicer to have Scott there.
When they started calling out raffle prizes, I really put my game face on. "I put in for a lot of stuff," I whispered to Scott. "If I don't win anything, I'm going to be furious."
Scott laughed and put his arm around me. "It's cute how competitive you are, even over something you can't control winning or not. And it's for charity."
I giggled. He was totally right.
Every time the DJ called out a number, I quickly ran my finger over my tickets. Around the fifth or sixth basket, I was beginning to feel discouraged.
I didn't win anything. Anything. I turned to Scott right before the last prize and while I wanted to scream, because yes, I am that competitive, I simply pouted.
"I know my boss really wants this one," I said as the DJ talked up the hotel prize. "But it'd be great if we won it. We could stay at the hotel when you come to visit next month"
Scott nodded and kissed my forehead. As they called out the numbers, I had a brief moment where I thought I won it, but I unfortunately did not.
For the third time that night, I heard that familiar voice before I even saw his face. Pete was standing up, a string of five tickets in his hand. He began high fiving the other people at his table and I almost rolled my eyes at how much he resembled his frat boy roots in that moment.
As he walked up to the front of the room, I turned to Scott and shrugged. "I'm glad it went to someone I know."
Scott laughed and rubbed my knee. "You're the cutest."
"I'm so glad to see so many familiar faces at the benefit here, tonight," I heard Pete begin to say. Nobody was giving a speech when winning a raffle. Was this normal or was Pete being a big weirdo? He continued rambling on about the company and all the wonderful employees.
"It's because of the amazing employees that I supervise that I enjoy coming to work so much. And I'd actually like to give this to one of our newest, but most ambitious, employees." Then, he said my name and I instantly felt my stomach drop. My face began to grow redder as more people turned to look at me.
"Caroline, you deserve this." Everyone began clapping and I awkwardly smiled at everyone. I thought Pete wanted this prize. He began walking toward the table and handed me the wine with the envelope. Then, in a very theatric way, he grabbed the wine out of my hand. People began laughing as Pete continued back to his seat.
"Wow," Scott replied. "Your boss must really like you."
I shrugged and tried to evaluate Scott's expression. I couldn't see if he was being genuine or not.
While I was still slightly embarrassed, it was a nice end to the night.