I watched the skies turn color as the sun set for the day. Florida had the most beautiful sunsets. They were much better than what New York had to offer. The skies would light up with pinks and yellows, casting a magical glow on the city below.

Tiffany and I were drinking on the rooftop at a bar on the beach. After our conversation at work on Monday, I decided to pick somewhere low-key for drinks. I actually wore jeans, which was rare for me. This bar was a typical beach bar. Good drinks, but nothing special. The beach scenery made up for the lack of pizazz that the bar had to offer.

Tiffany was already on her second glass of wine. I didn’t want her to get plastered, but I’d seen firsthand how the wine had loosened her up on Saturday night. I wanted her to talk to me about what was going on in her head. I wanted her to finally open up about her past and tell me about this man who broke her heart.

As expected, she was quiet at the beginning of the date. We chit-chatted about work, but I steered clear of talking about anything serious. I didn’t want to give her a reason to end this date early.

“I am sorry about earlier,” she suddenly spoke. I turned to her, surprised by her admission. Where had this come from?

“You’re sorry about what?” I asked. “You’re here with me now, it’s water under the bridge.”

She took a long sip of her wine before replying.

“I’m a mess, Cayden,” she confessed. “I feel like I need to tell you everything, so you understand where I’m coming from.”

I nodded.

“Tell me,” I said, getting closer to her. “I want to know everything.” I really did. I wanted to know her past, who had hurt her, and what I could do to make her feel better.

“His name was Brad,” she began. “We were best friends since sixth grade. He moved next door to me, and we were inseparable despite being very different. Brad was a chunky, overweight pre-pubescent boy and I was a bubbly, outgoing, skinny girl. When we were younger, I never thought about dating him. He was always “Just Brad”, my pal and confidant. I would go to him with boy problems and he would help me through them.”

She stopped to take another sip of her wine. I could tell she was getting emotional. I reached out and touched her leg.

“It’s okay,” I said. “Take your time. Or don’t. Just tell me whatever you feel comfortable with.”

She took a deep breath and began to speak again.

“After graduation, both of our fathers died within a few months of each other. It was a very hard time in both of our lives. Since I was going to college in Miami, I stayed home with my mom. Brad didn’t go to college. He got a full-time job to help his mom out with the bills. Our fathers’ deaths brought us together. It was just like one day, I knew we were supposed to be together.”

I nodded, letting her know that I was listening to the story.

“We dealt with the grief very differently. Brad began to work out, taking up running. Looking back, I should have done that, but I didn’t. I turned to food and TV. Brad was too busy dealing with his own sadness to notice mine. Not that I blamed him. I didn’t expect him to help me out of my dark hole when he was in his own. I gained a lot of weight over a short time.”

Ahh, the beginning of the insecurities, I thought.

“At first, Brad didn’t say anything about my weight. I think he thought it was a phase, and to be honest, I think I did, too. I thought I’d a good metabolism and if I started to work out, I would lose the weight. Except, I didn’t want to work out. I fell deeper into my depression. Brad stayed with me, but looking back, things began to change between us. Over the years, our sex became lackluster and he never went out of his way for me. He started spending a lot of time at the gym. When we were together, he would comment on my weight. He would tell me what I should or should not eat. He wanted me to weigh my food.”

“That’s insane!” I interrupted. She shrugged.

“I thought it was normal,” she said. “At the time, I thought he was just trying to help me out, even though my friends and family told me that he was an asshole. One night, we got really drunk and he proposed to me. He didn’t have a ring, but he told me how much he loved me, and I was the only constant in his life. Of course, I said yes and began to plan our future. But then things got even worse. I barely saw Brad and when I did, he was very distant. It was about a year ago when he told me he had been cheating on me with a girl from the gym. He was in love with her and was tired of being with an insecure, overweight woman. I haven’t talked to him since. He moved to Tampa with his new girlfriend and I was left here, picking up the pieces.”

As she wrapped up her story, she finished her glass of wine.

“And that’s that,” she said. I took a minute to comprehend everything she had just said. It was a lot, but I was glad that she had told me everything. Things were suddenly a lot clearer to me. I understood why she was so sad, why she was insecure, and why she was reluctant to get into a relationship with me.

“I am so sorry, Tiffany,” I said. I felt awful for her. I could not imagine going through what she had gone through.

“It’s okay,” she said.

“No, it’s not,” I said, suddenly growing angry at this Brad character. Treating anyone like he had was definitely not okay.

“You’re absolutely beautiful, Tiffany,” I said. “I know that I tell you that all the time, but I want you to believe it. I want you to see yourself through my eyes. You’re gorgeous. You’re put together. You’re smart. You are a hard worker. Do I need to go on?”

She laughed.

“No,” she said, blushing slightly. “I think I understand where you’re coming from.”

“Good,” I said. “I don’t care how many times I need to tell you, I want you to understand your worth. Brad was an asshole. I am sure he’s somewhere kicking himself right now for letting you go. But, I have to thank him, he made it possible for us to date.”

“Are we dating?” she asked. I nodded.

“This is our third date,” I said. “I think that constitutes dating, don’t you?”

“Yes,” she agreed.

“I know it’s hard, but you just need to open your heart to other men,” I told her. “There are good men out there, and I am one of them. I can guarantee you right now that I will never, ever do what Brad did to you.”

“How can you guarantee that?” she asked. “What if a hot blonde girl starts to work where we do, and you fall in love with her?”

I shook my head.

“It won’t happen. I’m not even looking at other girls, Tiffany. I just want to be with you. I want it to be easy. This can be easy.”

“Are you sure?” She looked up at me with her big, green eyes. I leaned over to caress her thigh and kiss the top of her head.

“Positive,” I said, grabbing her hand. “Want to go for a walk?”

We stood up, leaving our empty glasses on the table. I took a deep breath of the salty air.

“I will never get sick of this smell,” I told her. She laughed as we continued our walk.

“Thank you,” she said.

“For what?”

“Thank you for allowing me to open up to you,” she said. “I know I can be complicated, and I’m not guaranteeing that going forward there won’t be issues. I just hope you can be patient with me. I’m not used to this dating game.”

I squeezed her hand.

“I will be patient with you,” I told her. “I’m actually not a seasoned dater, either.”

She looked at me in surprise.

“What?”

I shrugged.

“I’m serious,” I told her. “I didn’t really date anyone but my late wife, and that was it.”

“Really?” she asked.

“Really. I’ve been so focused on work for the past few years that I haven’t taken any time to date since losing her,” I said.

“I can’t imagine going through something like that.

“I hope you never experience it.” I turned the conversation to something more positive. “I’m grateful for all of the past and the pain though. I have my little boy. He’s everything to me.”

She nodded. “Do you want more kids?”

I do,” I told her. “Two or three, maybe. What about you?”

“I want two,” she said. “A boy and a girl. That’s pretty standard, isn’t it? Brad didn’t want kids. I always thought I could change his mind, but as we got older, it became pretty clear that he had no intentions of being a father.”

“That’s too bad,” I said. “I have such a great relationship with both of my parents.”

“You would be a DILF, for sure,” she giggled. I knew that giggle. It was her drunk giggle.

“A DILF?” I asked. I’d not heard the word before.

“A dad I’d like to fuck.” She burst into laughter. Her laughter made me start to chuckle.

We walked along the shore, holding hands for a while. We talked more about the future.

“I still want to be a reporter,” she told me. “I took this fact checking job hoping that it will lead to better opportunities.”

“That’s a great reason,” I told her. “It can be tough to get into a publication, so the hard part is over. If there is ever an open position or a way to help you excel in your career, I am going to recommend you.”

She gasped.

“You can’t just recommend me because we’re fucking,” she said. I stopped her and looked into her eyes.

“Tiffany, I would not recommend you just because you were my girlfriend. I would recommend you because you have a strong work ethic. I could see you being a great reporter. You ask great questions at work and are really focused. You will go far, with or without my help, trust me.”

“Thank you,” she said, leaning up to kiss me. Every time I kissed her, I felt a spark of electricity run up and down my spine. I’d never felt that before, not even with Layla.

“Let’s go skinny dipping!” Her face suddenly lit up. It was now dark outside. We had walked far enough away from the bar that I didn’t think anyone could see us, but I was still a little nervous.

“Are you serious?” I asked, although I already knew the answer. She began to take off her top. Her breasts were held up with a black, lacy bra.

“Come on,” she said, dropping her shirt and running toward the water. I took off my shirt as well and followed her to the water.

“This is crazy,” I said, undoing my belt. Crazy, but exciting.

Her toes were in the water as she slid her blue jean shorts past her ass. They hit the sand. She was now standing in front of me in a matching bra and underwear set.

“I wore this just for you,” she said, signaling me to come closer.