The Week at the Hotel

Dean wakes up with a killer headache, must have been all the whiskey. He is confused for a second realizing he is at a hotel but he quickly remember all that has happened. Surprisingly Brooke has not tried to contact him but that was a good thing, he was moving on. He noticed his wedding ring was on, he removed it and put in on the end table, it left a tan line on his finger, he really never took it off in the short time they were married. Dean really didn’t have a plan for the day, only that he would go to the Tap That restaurant to try and see that waitress again. He decided to go back to sleep to get rid of his hangover.

Dean’s day was boring and lackluster, he woke up with just enough time to get some continental breakfast before it closed. He watched some TV in his room, used the gym at the hotel and swam in the pool. It was getting close to dinner time, he was excited to see the waitress again, maybe too excited. Dean decided to jerk off before going to the restaurant.

Dean walked over to the restaurant. He asked if he could sit at the specific table he sat at last night and they happily obliged. Dean hoped that the waitress always had the same section at the restaurant. Sadly he was greeted by a woman who was definitely not the girl from yesterday. He looked around the restaurant his entire dinner to see if she was around but sadly she was not, looks like it was her off day. Another night of disappointment for Dean but at least he had his whiskey.

Dean wakes up the next day not as hungover as the last day, is this healing? He can’t get the waitress out of his mind, he takes care of himself before getting out of bed to start the day. He went to the hotel gym once again, that was at least healthy for him. Dean really didn’t care to explore outside the general hotel area, he just wanted to relax so that’s what he did.

Dinner time rolled around and Dean hoped to see the nice, sweet waitress from the first day. This time instead of getting a table right away he decided to sit at the bar and scope out the restaurant section for the waitress. He sat down and got a drink and it didn’t take long for him to spot the waitress, she stood out from everyone, a natural beauty.

Dean quickly finished his drink and went back to the hostess stand. “Hello, can I get a table in her section, please?” Dean said while pointing in the blonde waitresses direction. The hostess turned to look where he was pointing and saw who he was gesturing towards, “Sure… right this way,” the hostess said as she grabbed a menu and sat him down at table.

Dean sat at the table patiently waiting for the waitress to come by, he hasn’t picked up the menu because he already knows everything on it since he’s has now been here for a third time. Dean looks down at his hands and sees his tan line on his ring finger and the absence of his wedding ring. His pondering is interrupted by the beautiful waitress.

“Hey there, sugar! Welcome to Tap That! I'm your waitress, Summer. Ready to have a good time?” She said with her sweet innocent smile.

Dean paid close attention to her this time, her name is Summer, what a nice name.

“Hey I was here the other day, remember?” Dean said.

“Oh, hey there! How could I forget? Of course, I remember you from the other day! What can I get you today?” She said still smiling sweetly.

“I’ll have whiskey again like yesterday!” Dean said happily.

“You got it! Whiskey it is, just like the other day. One whiskey coming right up!” Summer said as she walked away.

Dean was sort of nervous to talk to her, has he developed a small crush? She was different from other girls. He knows he shouldn’t feel this way, he’s older than her, successful, why should he be nervous to talk to a 19 year old waitress? He could tell she was a nice, sweet girl just by the way she talks.

Dean watched as Summer walked over with his drink, she dressed very conservatively, she didn’t have any cleavage showing even though she definitely had some large breasts.

“Enjoy your whiskey, and did you get a chance to look over the menu?” She said. Dean couldn’t help but admire her smile. Dean ordered some food. “Coming right up!” Summer said before starting to walk away.

Dean blurred out, “I’m Dean by the way.”

“Well it’s nice to put a face to a name, Dean.” She said and walked away.

After awhile Summer came back with Dean’s food and another whiskey, “Here you go Dean.”

“How is your night?” Dean asked her.

“My night's goin' great, thanks for askin', hon! Just chillin' here, chattin' with friends like you. How’s your night going?” She said. Dean can’t believe how nice she is, could it just be an act?

“It’s going good because I get to spend time with you?” Dean slyly said.

“Aw, you're too sweet, darlin'! I'm so glad I could brighten up your night. It's a pleasure chattin' with you!” Summer said smiling throughout the conversation. Dean thinks she sounds genuine.

“You have a nice smile, Summer,” Dean said returning a smile of his own.

“Aw, thank you so much! That's really kind of you to say.” Summer said while blushing.

“What are you doing after your shift?” Dean said being a little forward.

Summer looked a little throw off guard by the question, she broke eye contact and looked down at the table and then back at Dean and then her attitude changed slightly.

“After my shift, I might just head home and relax. Maybe watch a movie or hang out with friends. How about you? Any fun plans?” She said, she no longer sounded flirty but business like.

“No plans, Did you want to hang out?” Dean boldly asks.

“I appreciate the invite, but I'm afraid I can't join you tonight, it was nice chatting with you Dean but I have to get to my other tables.” Summer said. She left to go attend to her other customers.

Dean gets rejected again by Summer. He’s not sure what went wrong, she seemed like she was interested. Another night at the bar but this time he’s not drinking because of Brooke but because of Summer rejecting him.

Dean laid awake wondering what went wrong with Summer. Did he come on too strong? Is he too old for her? Not her type? She sounded interested up until right at the end of their conversation. Maybe he will try again another day before his stay at the hotel is over.

Dean spent the next couple days avoiding the Tap That restaurant, he didn’t want to come on strong or seem like he was stalking Summer although he was a little infatuated with this girl, she just seemed too good to be true. He continued to use all the amenities at the hotel, the gym, the pool and ventured a little further from the hotel to different restaurants but none of them had a girl as beautiful as Summer.

A couple days have now passed since Dean’s last interaction with Summer and hopefully he will be successful in wooing her this time. He arrived at the Tap That restaurant, he dressed nice and was well groomed. He scanned the restaurant and he saw her, Summer, just glowing. The hostess seemed to recognize Dean and showed him to a table in Summer’s section.

“Back again are we?” Summer said. Dean thought she looked happy to see him. He chuckled, not sure what to say. “The usual?” She asks him. “Yes of course,” Dean says with a smile.

Summer came back shortly with Dean’s whiskey. “Here you go Dean,” she said.

“Thank you, Summer.” Dean said. He wanted to get to know her more, “I hear you have an accent, where are you from?”

“Well sugar, I’m an Oklahoma girl through and through, where y'all hail from?” Summer asked.

“I actually live a couple towns over,” Dean said.

“What brings ya to this neck of the woods?” Summer asks sincerely. Dean didn’t want to divulge the actual reason and get into too deep of a conversation, “…just a staycation, but I’m glad I came in here,” He smiled at here. Summer blushed, “Well, I appreciate the kind words. Now, what can I get for ya today? Just let me know what tickles your taste buds today!” She said.

“I’ll get…” Dean tells her his order, “and I’d like to know what brings you here from Oklahoma?”

“Y'see, I came to this big ol' city for a fancy job, but it just didn't pan out. I reckon God's got a plan for all of us. Sometimes things don't work out the way we expect, but it's all part of a bigger picture. So here I am, slingin' plates and chattin' with good folks like you. Life's full of surprises, ain't it?” She smiled and was off to put Dean’s order in. Dean was making progress with Summer, he was starting to learn things about her.

Dean tried to sweet talk her with the limited time he had when she would come to the table and check on him. He ordered a few more drinks than usual so she would come by more and even got dessert which he normally doesn’t have just so he could have more time to talk with her. It was getting late and was about that time where Summer would say it was the end of her shift so Dean had one last time to put himself out there.

Summer walked up with his check in her hand, “It’s that time of the night…” she said.

“Would you want to stay and chat for a bit after your shift?” Dean asked.

“Uh…” Summer paused and looked down at the table and then back up, “Aw, darlin', I appreciate the offer, but I gotta stay true to my values. I can't go on a date with a married man. I believe in respectin' commitments, y'know? But I'm sure there's someone out there who'll be just right for ya,” She said.

Dean was surprised, “What… how…?” Summer interrupted him, “Well, sugar, I can see that tan line where a ring is supposed to be, and it's clear you're married.” She was pretty observant. “We are actually not together anymore…” Dean said.

“Aw, darlin', I'm sorry to hear about your breakup with your wife. That can be a tough time. If you don't mind me askin', has the divorce been finalized yet?” Summer asked with intrigue. “Well… no, not yet at least.” He said knowing that wasn’t the answer she wanted to hear.

“Aw, sugar, I understand that you're going through a difficult time right now. Once your divorce is finalized and you've had some time to heal, feel free to reach out. I'm here to support you, whether it's as a friend or just someone to chat with. Take care of yourself, okay?” Summer said. Her shift was over and she left to go home.

That didn’t go exactly horrible nor was that an actual rejection either. Dean didn’t stick around to drink this time, he was hopeful he would see Summer in the near future. He headed back to the hotel, tomorrow was check out and he would be heading home, it’s been a week since the whole Brooke fiasco. Dean hoped she moved out like he told her to, he hasn’t heard anything from her that whole week, no phone calls or texts.