Valentine's Day Hookup

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

...

In a way, Tom felt he was lucky he didn't have to deal with Valentine's Day. He was a man, after all, and that kind of obsession was usually reserved for women. Men never get into it unless they're involved with someone they care about. Other than that, if you're not involved with someone, then it's just another day for them to watch TV and save money from having to buy gifts and fancy dinners.

He wouldn't have minded participating in the holiday if he did have a girlfriend to dote on during this time. He did have a little fun with it in previous years for this holiday, especially with women he really liked. But he ended things with his girlfriend of the last year, Sarah, a couple weeks earlier. To be more precise, she ended things when she confessed that she had been seeing someone else for a while and loved him more. Furthermore, she said she wanted to break things off with Tom so she could be with her new beau during Valentine's Day.

Tom played it cool so he wouldn't give her the satisfaction of knowing her betrayal hurt him. But in reality, it hurt him deeply. He had heard people use the metaphor of betrayal feeling like a knife being plunged into your heart, but he never truly understood how real that expression felt until then.

He pretended he was alright with the situation, but when he got home, he was so pissed off he screamed and punched a hole in the wall. It momentarily made him feel better, until he realized he had to bandage his knuckles and then fix a hole in his wall. He did a bad job plastering the wall, so he just covered up that spot with a picture frame which somehow only added to the misery of it all.

After a week of sulking, his friends convinced him to go out with them to a strip club. It was kind of a clichéd idea to help a friend get over a woman, but he wasn't going to argue about it and decided to go along with it to have some fun for one night. He saw plenty of beautiful naked women dancing on stage, got some lap dances from a few of them. By the end of the night, he was having a lot of fun and wasn't thinking about Sarah at all. He even got one of the dancers' phone numbers; he was sure it was a prostitution thing, but he still liked it nonetheless.

After that night, he felt a little better about his breakup and was even looking forward to the idea of dating again. That was until Valentine's Day, when almost every woman in his office was getting flowers and candy delivered to them. Tom had done this before with Sarah and a couple of other past girlfriends. Women appreciate it when men have these gifts delivered to them as a public display of affection, letting others know they have someone in their lives who cares enough to give them gifts for the holidays.

Tom did his best to be cool about it. He told himself that this was more of a woman's holiday, and men only get into it because they might get laid if they do a good enough job. He made a lot of excuses for to put down the holiday, but deep down he despised the fact that he had no one.

He decided to text a couple of his close friends, Vincent and jeff, to get some perspective about what he was going through.

Tom: "I don't understand how is Valentine's Day having an effect on me? I'm a guy, I shouldn't give a damn about this."

Vincent: "You're only human. Also, you were with Sarah for almost a year so that makes it worse. It's not like you two were only together a few weeks."

Tom: "Good point. But I feel like a pussy for letting it get to me like this."

Jeff: "That's because she broke it off not that long ago. If she ended it a couple of months ago you would've been over her by now and hooking up with someone else."

Vincent: "Yeah. Who does this so close to Valentine's Day?"

Jeff: "A cheating bitch. That's who"

Vincent: "Yeah. Fuck her. Don't let her have this effect over you, bro."

Tom thought they had a good point. He would've felt better about it if Sarah had broken up with him a lot sooner instead of doing it so close to Valentine's Day. At least then, he'd have more time to get over the breakup and may even have started dating someone by now. But she did it so close to this Valentine's Day, which only added to his heartache.

He was working in his cubicle, focusing on his work, when a delivery man came to the cubicle across from him to drop off some more flowers. This time it was to one of his favorite coworkers, Blair. Although cubicles used partition walls to separate the desks from a few others around you, in their office there were two sections of cubicles separated by a pathway, and some people could see across the pathway into the cubicles of some of their coworkers.

Blair was not only one of his favorite coworkers and close friends, she was also a longtime crush of his. She started working at the company several years ago, about one year after Tom started, and he immediately had a thing for her. But at the time, she was briefly engaged to another man. He noticed the ring right away and made sure he wouldn't hit on her.

She was a beautiful woman. She was in her early twenties, had short blond hair, and always wore skirts that weren't too short but always showed enough of her legs. She had a good figure too; she liked to hit the gym and take yoga classes. Tom had seen her in dresses before for office functions and could tell she had good-sized C-cup breasts.

They hit it off right away when she started asking him for help with her assignments. She was good with computers but had trouble learning everything else. So, Tom, who had been with the company a few years already, became kind of a mentor to her; he showed her how things were done in the office and how to do her job effectively. During that time, they got to know each other and became good work friends. They both liked that they had someone to hang out with at work and sometimes after work when the situation arose.

A few months later, Blair's engagement fell apart, and she was a free woman again. By that time, Tom began seeing Susan from accounting. He still kind of had a crush on her, but things were going well with him and Susan. A few months later, he and Susan broke up, and Blair began seeing another man.

This was a pattern for them both; neither of them was ever single at the same time for Tom to make his move on Blair. There were a few brief periods where they were both single, but nothing happened. There was one time he and Blair were single for a month, but somehow he didn't know about it until she began dating someone else, and he hated himself for missing his best opportunity.

Despite it all, Tom still liked that Blair was his friend. He liked having someone to talk to at work and sometimes after work if the situation called for it. They hung out with other people at work, but they usually gravitated toward each other. If it wasn't for the fact that they were often seeing other people, he was sure there would've been rumors of them sleeping together.

The flowers Blair received came in a red vase, consisting of red and pink roses mixed with blue iris. It was a good arrangement that even Tom was impressed by.

"Those look beautiful," said Tom. "So far the best one delivered today in my opinion."

"I know, I love them," she said. "And the card Michael wrote was very sweet."

Although she was smiling, Tom noticed that she wasn't as enthusiastic about the flowers as some of the other women in the office were.

They later met up with some other coworkers in the breakroom for lunch. Many of them discussed their plans for the holiday. Tom just sat there, hoping nobody would ask him anything. It was already known that he and Sarah broke up, so it was possible they were just being nice by not bringing it up.

The conversation was making Tom feel worse about his situation, so he did something he didn't think he would do. He found the number of the stripper on his phone and texted her. He had to remind her of who he was, which to him meant that she had given this number to plenty of other guys. After she remembered who he was, she said she was available to come to his place tonight and how much it would cost him. Part of him hoped she wasn't a hooker and she just thought he was cute enough to give her number to. But he knew that was only wishful thinking. He agreed on the price and texted her his address and the time to meet.

He did this all while everyone was talking about their plans. After he was done texting the stripper, he noticed Blair was somewhat quiet about her plans for Valentine's Day but didn't bring it up.

Later on, they were alone in the filing room, getting some information they needed for their clients. The work was boring, so Tom decided to change the topic of discussion.

"Does Michael have any plans for you tonight?" Tom asked. "I noticed you were quiet about it in the breakroom."

"To be honest with you, Michael and I broke up several days ago," she revealed.

"Seriously?" Tom said, taken completely by surprise.

"I caught him cheating on me."

"That seems to be happening a lot lately," said Tom, making a joke at his own expense.

"That's why he sent those flowers; he's been trying to apologize to me ever since and probably thinks he could use the holiday to play on my emotions and get me to go out with him later."

"Do you really think that's the reason?"

"You're a man, you tell me. This is mostly a women's holiday; we're the ones who obsess over it the most. This holiday means nothing to you guys; it's just a chance for you all to get laid if you do a good job treating us right for one day."

"I wouldn't put it like that," said Tom, pretending he never had that exact thought.

"Don't get me wrong, I'm not happy that I don't have a date for Valentine's Day, but I'm not going to let him emotionally blackmail me like this."

"No, let him be miserable and realize what a big mistake he made."

"That's right," she said as she raised her hand to receive a high-five from Tom.

They both went back to work and changed the topic of conversation. While Blair was going on about a concert she was looking forward to seeing in a couple of weeks, Tom realized that they were finally both single at the same time and had a great opportunity to finally ask her out. But he figured it would be better to wait until sometime after this holiday was over. He didn't want her to think he was somehow using the holiday to get her to have dinner with him, like she suspected her ex-boyfriend of doing. He figured in about a week, assuming nobody else made their move ahead of him, he would ask her out.

Then Blair did something he did not expect. After they got what they needed from the filing room, they made their way back to their cubicles. They were alone as they walked down the long hallway, continuing to talk about a few things, and the subject of Netflix shows they've been enjoying came up.

"I just had an idea," said Blair. "Since neither one of us has plans for tonight, why don't you come over to my place?"

"You're place?" he asked.

"Yeah, I figure we cozy up on the couch together, chilling out as we watch something on Netflix."

Tom did his best to hide his surprise. He basically heard her say Netflix and Chill, which is usually a code for a hookup. But from the way she phrased it, it was also possible she just wanted to hang out as friends.

"So, just the two of us?" he inquired, suspiciously.

"Yeah, my roommate will be spending the night at her boyfriend's place, so we have the entire place to ourselves to do whatever we want."

He was still hearing her suggest a hookup but wasn't entirely sure. From how she said it, it was still possible she was just suggesting they hang out together. He wasn't sure if he should be listening to the dirty part of his mind or the rational part of it.

"You don't have any other plans tonight, do you?" she asked.

"No, not at all. It sounds like a great idea," he answered.

"Great, it's a date then," she said enthusiastically.

"Should I bring anything?"

"Just your sexy self," she said as they separated for their own cubicles.

Again, he wasn't sure if that comment meant something or if she was just being playful. He had had female friends before say things like that to him and other male friends of theirs, but it never meant anything. But there were a lot of things adding up together, which could mean a lot more than she was saying.

Tom suddenly remembered the stripper he had been texting earlier and was going to pay for sex. He was only going to hire her because he was feeling lonely, but he never felt good about it. Now he has some much better plans. Even if she didn't mean what he thought she meant, it was still a good evening with a beautiful woman.

He texted the stripper and told her he changed his mind about it. She tried to entice him to change his mind by sending him a cute photo of her in a bikini. It almost worked, but he couldn't do it. She texted back saying she understood and he could visit her at the club whenever he wanted.

Over the next few hours, Tom continued to wonder what tonight meant for Blair. Should he expect a hookup, or was this just a friendly get-together? They have hung out together plenty of times outside of work; most of the time it was with other people, but there were a few times when it was just the two of them. But he couldn't get over the way she suggested what she wanted to do later on.

He decided to ask a couple of his friends for advice on the situation. When he found time at work, he went on a long break, went to his car for some privacy, and got two of his friends on his phone for a conference call. This was too important to talk about through texting alone, and needed to talk to them directly. He had a couple of male friends at work who he sometimes talked to about these things, but he didn't want to risk them telling other people about it.

He got his friends Jeff and Vincent on the conference call. They were surprised to receive a phone call rather than a text, but when Tom explained his situation, they understood. They asked him to tell them the story a couple of times to make sure they got every detail correct.

"It's a booty call, bro," said Vincent.

"Yeah, no question about it," said Jeff. "Why else would she be suggesting this on Valentine's Day of all days?"

"Are you guys absolutely sure about it?" Tom asked. "I don't want to go there and make a complete fool of myself."

"Don't worry about it, she's totally into you," said a new female voice on the phone.

"Who's this?" Tom asked. "Amy, is that you?"

Amy was Vincent's girlfriend.

"Yeah, it's me," said Amy. "Vincent put me on speaker so I could listen in."

"Oh, my God," Tom said, feeling embarrassed. He didn't want to talk about it with his friend's girlfriend, whom he barely knew.

"Trust me, this is a booty call," said Amy. "She just doesn't want to say it out loud without looking desperate. That's why we have codes like this to say it without saying it."

"I would listen to her," said Jeff. "Also, I just relayed this story to Stephanie, and she agrees."

Stephanie was Jeff's girlfriend. This only made Tom feel worse since more people know now.

"Listen to me, Tom," said Amy. "She's only pretending she's OK with her breakup. But really, she's emotional about it and just showing a brave face."

"Stephanie agrees," said Jeff.

"You might as well get Stephanie on the phone if she's also going to get involved," said Tom.

Jeff put his phone on speaker so Stephanie could chime in.

"She's vulnerable, like Amy said," said Stephanie. "She's probably thinking about calling her ex-boyfriend, which she doesn't really want to do. So, she's using you to avoid that."

"So, I'm a rebound booty call? I'm not sure if I want that. I really do want to go out with her."

"Maybe you are a rebound fuck, who cares?" Stephanie continued. "If she picked you for this, then she probably likes you too and is using the opportunity to give you a chance with her tonight."

"And if all goes well, you may see her again for a real date," said Amy.

Tom knew they were right. With everything going on, this could be the opening he needs to finally go out with her before something else gets in the way of it. He was now happy that his friends' girlfriends had heard everything and given him advice. He probably would've listened to Jeff and Vincent anyway, but it was their girlfriends who helped put more perspective on it.

"Should I bring flowers?" Tom asked.

"Yes!" both women answered at the same time.

"And dress nicely. She'll love that too," said Amy.

"Is a booty call a situation to dress up for?"

"Normally, no, but for Valentine's Day, yes," said Stephanie. "I'm sure she's already planned a nice dress for herself to wear tonight to impress you."

"She probably has some lingerie she plans to wear for you in the bedroom, too," said Amy.

There weren't many good flowers left in the city because of the holiday. It took him an hour of calling around to find the one place that had a decent bouquet of roses, which cost him $150. The store was obviously taking advantage of men getting flowers at the last minute. Despite knowing this, Tom still bought those flowers.

Before he left his apartment, he shaved, cleaned himself up pretty well, put on some good cologne, and found a nice outfit to wear. He left his apartment, very excited about his prospects. A friendly neighbor saw him walking down the hallway dressed very well and holding those flowers, and he had a good idea of what Tom was in for. The neighbor gave Tom a fist bump and wished him luck. This only improved Tom's confidence for tonight.

When he got to Blair's apartment, he was greeted by her roommate, Carol, who let him in. Carol was also dressed well and was just on her way out to meet her date for tonight when Tom arrived.

"She's still getting herself ready," said Carol, and she called out to her roommate. "Blair, Tom is here."

"Tell him to wait for me in the living room!" Blair yelled back.

Tom commented on how well Carol looked for her date tonight, and she thanked him. She gave Tom a good look up and down, seemingly giving him an approved look.

"You two are... hanging out tonight?" Carol asked.

"Yes, she invited me to come over," Tom replied.

Carol had a concerned look on her face that made Tom apprehensive.

"Is everything alright?"

"I'm sure it is," said Carol. "I just think you might be... a little overdressed for what she had planned."

"Maybe a little, but I think it's ok," said Tom. "Why do you think I'm overdressed?"

Carol took a long moment to answer, which again made Tom a little nervous about why she was behaving this way.

"Never mind, you look great," she answered. "I'll just leave you two alone for the night, and whatever happens, happens. Good night."

Carol rushed out the door before Tom could also say goodbye. Her behavior worried Tom a little, but he didn't think much of it at the moment.

He went to the living room, where Blair suggested he wait for her. There, he was surprised to see an unopened pizza box on the coffee table, along with a six-pack of beer and the TV set for the Netflix home screen.

A moment later, Blair walked out of her bedroom and met up with Tom in the living room.

"I'm glad you made it," she said with a big smile, which went away as soon as she got a good look at Tom.

While he was dressed up for a nice evening and had flowers in his hand, Blair was not wearing a nice dress that he was convinced she was going to wear tonight. Instead, she was wearing slippers, dirty jeans, and a Friends TV show t-shirt. His heart sunk when realized he had misread the entire situation between them and that she really did just want to hang out and watch something on Netflix. He had never felt more foolish in his life than he did right now. Even seeing the word "FRIENDS" in big letters on her t-shirt made the whole situation feel much worse for him.