Our Story: Date One

“I don’t know what to wear. I can’t do this. I’m not going to go!” I lamented to my roommate on the phone as I was driving home from work.

“It’s ok…I’ll lay out a couple outfits for you. You are going!”

“Can I wear my black cowboy boots?” I asked, remembering the last time I wanted to wear them on a date. My sister had cautioned me, “Let him get to know you before you scare him off.” I didn’t wear my boots that night.

“Sure – I’ll pick out a black shirt!” My roommate encouraged.

After much counsel and encouragement from my roommate, who was convinced this was the “last first date” I was ever going to go on (I should have known to listen to her-she’s always right!), I was on my way to meet Jesus for dinner. The knot in my stomach grew bigger and more twisted the closer I got. The last several dates I had been on had not ended well. Either the date was awkward or there was no connection or I chickened out or he turned out to be unreliable. I needed this date to go well, just to prove to myself that there was nothing wrong with me. When the common denominator in several failed attempts is you, you start to question yourself.

I parked in the parking lot at his school and started to walk towards his car. As I grew closer, I could smell his cologne from several feet away. Remembering a recent conversation we had, where he said guys only wear cologne if they are trying to impress someone, I became a little more at ease. An awkward greeting and short car ride later, we had arrived at Plantain Café.  

We sat at a high table close to the window, and perused the menu. Scanning the menu of the various Cuban foods, I was unsure what to order. As my usual protocol at new restaurants, I avoid ordering anything with vegetables. I saw a Cuban sandwich and plantain chips listed. Seeing nothing I objected to, I ordered it. Other than agreeing to go on the date, this was the best decision I made all night. The slow-roasted pork, sweet ham, dill pickle, and melted Swiss cheese was a heavenly combination for my taste buds. I took half my sandwich home with me, which I ate at work two days later and reveled in the memories of the date.

Once we had ordered, Jesus finally broke the ice.

“Ok, I have to tell you. I’m really nervous. It’s been a while since I’ve been on date.”

It was as if saying those words erased all the pressure, all the awkwardness, all the nerves. We invited the elephant in the room to join us for dinner, and in doing so, livened up the evening. We broke the unspoken first date rule and talked about previous dates. I confessed I had been burned recently and he confessed he hadn’t been interested in anyone in a while. We laid all our cards on the table, and cleared the air of expectations. We agreed we just wanted to have a good date and enjoy the evening. With the pressure to impress the other person gone, we were able to open up and have honest conversations.  

After dinner, we drove to the Mexican market to look for Cajeta, a goat milk caramel-like syrup. Jesus remembered me telling him how much I loved eating it while in Mexico and I was unable to find it since being home. We found in in the market, and grabbed some Concha bread for the road. Jesus was so busy talking in the car that he didn’t notice he turned the wrong way out of the market and ended up taking the long way back to downtown. I didn’t mind, it was cold out and the car was warm and we were having great conversation. We told each other about our churches and our upbringings. We talked about our families and our traditions. We talked about life goals and dreams for the future.

Once back downtown, we walked through several art galleries. We stopped in a coffee shop and had hot chocolate (I hadn’t yet converted Jesus to the dark side of coffee yet) and our Concha bread. After walking through the cold, snowy streets for hours, we reveled in the warmth of the hot chocolate.
When Jesus excused himself to go to the bathroom, I frantically texted my roommate an update. She excitedly encouraged me to enjoy the evening. I believe some form of the words “I told you so” were included as well.

On our way back to the car, Jesus said something that confirmed my decision to go on this date: “By the way, I really like your boots.”  I knew immediately not only had I made the right fashion choice, I had also made the right date choice. If he liked me in my boots, then he really liked me. I made a mental note to tell my sister that she was wrong about the boots, because I found someone who liked them just as much as I did.

As we were walking, we were approached by a homeless man. He was working with a local organization that helps the homeless get back on their feet by selling newspapers. He was only asking one dollar per paper, but Jesus handed him a five. He smiled and handed us a second paper.
“Take one for your girlfriend, too” he said.

We were both awkward and stuttered thank you and walked away. We avoided the “we’re-not-together” conversation, and instead talked about homelessness in our city and what we could do about it.

Once back in the parking lot, I checked my phone. My mother had called to check on me. She was concerned that I had been with an unknown man for six hours and wanted to make sure I hadn’t been kidnapped. I explained to Jesus and sent her a message to let her know I was still alive.

“I didn’t realize it has been six hours. I should probably get home,” I told him.

“Ok. I want you to know, I really enjoyed this evening. I think we both needed this. It was a really good date.” He responded.

Little did I know that was the first of many really good dates. 


  1. Love the recap of your first date! And you know your mom was right when she told you that when the right one comes along the rest will not matter! Great pics, too!


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