She was very cute, kind of petite, and even though she was rather plain looking, and came across very innocent, she had an allure about her. She seemed kind of shy but I sensed she was hiding a more playful side. Her name tag simply said, “Ashley,” and as I continued to check her out as she made my drink, I couldn’t help but smile thinking how nice it would be to be with her.

Like I said, I could tell she had a slight frame under that green apron, but the way she carried herself was attractive. She had hazel eyes and dark brown hair that she always had in a ponytail, and whenever she would French-braid it, I found her very sexy. She had a nose piercing and I could see she had a few tattoos on her arms, which only exemplified that she probably had a wild side.

From the first time I saw her, I was curious, and tried to visit this particular Starbucks whenever I could, just to see her, always wanting to interact with her. As time went on, I found myself obsessively wanting to see Ashley every morning, hoping I’d find a way to ask her out, but it never presented itself.

I always tried to flirt with her and made sure to give her a generous tip after ordering, always thinking she’d realize I was interested. I didn’t want to come across desperate and never came right out and asked her but continued to search for ways to let her know I was attracted to her. I even went so far as to contacted the manager and Starbucks directly to compliment her, again hoping she’d notice the attention I was trying to give her, how could she not.

I wanted her to feel obligated to reach out to me too, but she never did, until one afternoon, I decided to stop in to see if she might be there as I headed home from work,. It surprised her a little I think as I walked in, but after a double take, she smiled. Approaching the register, I tried act nonchalant but eventually as we looked at each other, we smiled. It was obvious she wasn’t expecting to see me in the afternoon, but after a pause I innocently asked, “How’s it going?”

This made her blush a little, and then after giving me my coffee, I said thanks and casually went over to sit at one of the tables. Sitting there contemplating my next move, I hoped she might get the hint and come over and talk with me. Continually looking over, trying to get her attention, she eventually did venture over and when she asked, “Can I get you anything?”

Searching for something to say, I nervously shifted in my chair. I didn’t know what to say, and as I looked at her, I hoped the words would miraculously come to me. I wanted to ask her out and after exchanging some simple pleasantries, I nervously asked, “Do you want to sit down.”

Smiling, she glanced back at the counter briefly and then feeling a little obligated, she eventually sat down. I could see she too was searching for what to say, and then when she blurted out, “Thanks for sending those complimentary emails to my boss.”

I couldn’t help but look at her questioningly and thought to myself, “How did she know,” but quickly realized it was probably obvious.

As I looked at her, struggling for what to say, she questioningly asked, “It was you, right?”

Smiling I nodded and said, “Yea, you’re a great barista.”

This made her smile too and after a second or two she again said, “Thanks.”

As we talked, I couldn’t help but nervously flirt with her, all the time hoping to get up the nerve to ask her out. However, I could see she too was a little nervous, and soon said, “I better get back to work,” as she stood up.

I’m sure she realize there was a mutual attraction, and not wanting to loose the opportunity, I said, “Thanks for talking.”

Smiling, Ashley said, “Sure,” and just as she turned to leave I boldly asked “Hey, would you like to go get a drink sometime and talk a little more?”

Ashley seemed hesitant but then after looking over at her colleagues by the counter, she turned back and smiling simply said, “Sure.”

I couldn’t believe it, but then as we looked at each other, Ashley glanced at her watch and said, “My shift is over in a little bit.”

I was speechless, but then she asked, “Do you want to wait.”

I couldn’t believe it, but then realizing it was my chance, I smiled and confidently said, “Of course.”

This made Ashley smile and after a subtle little nod, she went back to work.

“Oh my god,” I thought as I sat there nervously watching her walk away, I couldn’t help but continually look over at her.

She was talking with some of the other baristas and when they looked over at me smiling, it was obvious Ashley had told them what was going on.

I’m sure she could tell I was much older and I tried to ignore the fact, hoping it wouldn’t get in the way, but it was constantly in the back of my mind.

Eventually her shift ended, and when she came over to where I was sitting, I smiled at her and stood up to greet her. Taking off her apron now she asked, “Where do you want to go?”

I couldn’t help but check her out as she rolled up her apron, wanting to soak her in. She really was small, but I was so excited, and not realizing I was staring, I hastily looked back up. I was a little embarrassed, but smiling she suggested, “How about Chili’s,” and then explained, “It’s close by.”

It sounded great and after a smile and a nod, I agreed. Ashley continued to smile and as we headed out, she waved to other baristas. In the parking lot I asked, “Do you want me to drive?”

Ashley immediately said, “Why don’t you follow me.”

At first, I was a little worried, but then realized she just wanted to drive her own car. It was probably best, I couldn’t blame her and being I was really nervous, I simply said, “Okay.”

Following her, I felt this was my chance, and not wanting to blow it, I tried to gather my composure before we got there. I had wanted this and as we walked into the restaurant together, I hope the right words would find there way into our conversation.

We decided to get a booth and after ordering some drinks, and an appetizer, we immediately started asking each other a lot of questions, trying to get to know one another. I was curious about her and I think she was too. I wanted her to know I was interested in her too and when I eventually asked, “How old are you?” There was a brief pause.

Ashley then smiled and asked, “How old do you think I am?”

I didn’t want to embarrass her or myself but eventually said in a questioning voice, “25?”

There was another pause but she again smiled and said, “No, I’m 22.”

Ashley definitely carried herself more mature, or maybe she was nervous, in either case, being she was so much younger she still seemed very innocent. As she looked down, sheepishly smiling, I nervously thought, “There’s no way this is going to happen.”

I wanted to keep our conversation going, and as I searched for what to say, I grabbed my drink and took a big pull off the straw. Ashley immediately looked back at me and as I put my drink back down she asked, “How old are you?”

Nervously looking over at her, I smiled and said, “Well, I’m a lot older.”

Smiling, Ashley pressed me, saying, “Come on, you’re not that old.”

I didn’t want to tell her just how much older I was but I could tell she was waiting for me to say something, and after clearing my throat, I smiled at her and hesitantly said, “I’m 50.”

She seemed a little shocked but after a moment, she smiled and said, “You don’t look that old,” and as I continued to look over at her, she said, “I thought you were maybe in you late 30s.”

Cautiously smiling as we looked at each other I jokingly asked, “Maybe I’m too old for you?