A Flirting Workshop with My Sister

Z added, "There are a few guys in my classes and in my dorms who I've gotten friendly with. I can't imagine dating any of them either. If I had a boyfriend, then things would fall apart with my guys. If one of my guys got a girlfriend, I'd stop being their sweetheart. I'd start seriously flirting with one of your other friends and try to convince them to join the movie-watching nights."

It bothered me that my sister was giving up dating for my friends. "You could get a boyfriend. Just don't tell Dimitri, Rob, and Landon about him."

Z snorted. "And not go out with my boyfriend on Friday and Saturday nights?"

"Well, maybe he goes home on Friday afternoon to work five shifts over the weekend at some fast-food place to pay for his college."

I could practically hear Z roll her eyes. "I haven't met any guys with a crazy schedule like that. And I couldn't lie to my guys about not having a boyfriend. They'd see me holding hands with him someday."

"Well, if he was your secret boyfriend..." I decided to let the subject drop. My suggestion was weak, and I couldn't think of a better one.

After a while of listening to the music, Z asked, "Can I ask you something personal? I don't know if you can answer it, but it's something that's been bothering me."

"Shoot."

"When Katharine was a cheerleader, she and some other girls would get together with an equal number of football players, and they'd have a sex party. She did that numerous times. Sometimes she'll bring that up. She'll tell me that in twenty years, we'll both be married with kids, living a boring life like our parents do now. She'll have those crazy memories to look back on and smile. All I'll have is my relationships with the loser and Brett. That's one of her justifications for pushing me to do more than I'm comfortable with. 'Make some memories for twenty years from now.' Do you think I'll regret when I'm older not having done crazy stuff in high school?"

I thought over her question for a while. "I can't tell you what you or I will think in twenty years. But I think I know the answer. Pre-med is really stressful, right? Well, all of us pre-med students need to have a way of blowing off steam to keep us sane. Friday and Saturday nights are usually our only chances to let go and do something fun."

"Like movie-watching nights."

I nodded. "Probably the most common way of blowing off steam is binge drinking."

"But Mom and Dad told you many, many times to not do that. They told you about lots of people who developed permanent drinking problems from that. You don't binge drink, do you?"

"I did once. So many of my friends told me binge-drinking stories that I had to try it. I did not enjoy throwing up. They had made it sound almost fun. It was miserable." I shook my head at the recollection. "But back to my point - probably the second most common way of blowing off steam is hooking up. Do all the sex you can do for a night or two, and then go back to being friends. I hooked up last fall. Landon did, too."

"You did? I guess I shouldn't be surprised. People have mentioned to me about pre-meds hooking up when I've talked about hanging out with you and my guys. What did Rob and Dimitri do?"

"Dimitri did binge drinking. He'd show us Americans how Ukrainians can drink so much more than us. Rob really enjoys bartending. He'd bartend parties and hook up with girls at the end of the party."

"Did all of you do that the whole year, or just last fall?"

"Let me give you the full timeline. That was how the fall semester started. Then at the beginning of November, Landon started hooking up with only one girl. They kind of became a couple. That inspired me to find a girlfriend, Tracie. Dimitri continued binge drinking, and Rob continued his bartending. Two weeks before spring break, Landon asked his girl to come home with him. She told him she didn't want to; that it wasn't a serious relationship, and that she wanted to be able to walk away from it at any time with no hard feelings. Landon thought they were more serious than that. They broke up a week later, and he started binge drinking with Dimitri."

"Poor Landon."

"Yeah. Then in April, Dimitri woke up on a Wednesday morning with a massive hangover and no memory of what had happened the previous night. It scared the hell out of him. He realized his binge drinking was getting to be a problem, and that he had to give it up. He came to me. As he had never seen me drunk, he begged me to do something with him on Friday and Saturday nights to keep him from drinking. As I could see the writing on the wall with Tracie, I broke up with her and started going to the movies with Dimitri. By the end of the school year, we had run out of movies we wanted to see. And then we went home for the summer."

"How did you meet Tracie?"

"She lived down the hall from me. We'd talk whenever we ran into each other. She was nice and good-looking. An art history major. I started eating meals with her. And then we were a couple."

"Why did you break up?"

"Because after a while, she stopped enjoying being my girlfriend. Things started great. She was very supportive. She'd do my laundry and buy things for me at the store. I think she might have been looking for the M-R-S degree. My top three priorities at school are my classes, my classes, and my classes. When she never broke into the top three, she started souring on the relationship." I swallowed. I still didn't like how I had treated her. "Being a pre-med student is something like being an Olympic athlete. You've got only one chance at success. You can never break training. You can never let yourself get the least bit behind. You have to nail every test and assignment. There's no margin for doing just okay. And that doesn't leave time to be the type of boyfriend I want to be." One of the many things I didn't like about being a pre-med. "But I brought this up to tell you about hooking up. As I'm one of the better-looking pre-med guys, I got a lot of attention from my female classmates. I had no problem hooking up every weekend. I wound up having sex with twelve different girls during the fall semester, all of them very smart and good-looking."

"Sounds impressive."

"I think so. But when I think about being with a girl, I think about Madison." Madison was my girlfriend my junior year of high school. "I loved her, and she loved me. We'd cuddle and talk on her bed, and it was like magic gold letters would appear over our heads spelling out 'forever'. It's nice that I've punched the 'Had sex with twelve different smart, good-looking girls in one semester' square on my lifetime achievement card. It came up a few times last summer when I was talking with friends back home. But already, I reminisce more about Madison than all of those girls combined." Man, I still missed Madison. "If you're the type of person I think you are, then if Katharine had invited you to some of her sex parties, twenty years from now you'd think much more about Brett than those parties."

Z was quiet for a while. "Thanks. That answers my question. And I like that answer." She reached over and squeezed my hand. "Have you talked with Madison recently?"

"I emailed her at the start of last school year, asking how she was liking school. She goes to UCF." At the end of my junior year, her dad had gotten a promotion that required moving to Miami. She had moved as soon as the school year ended. "We don't have anything in common anymore."

"Brett...wanted to keep dating. He wanted me to come home every weekend."

"It wouldn't have worked." Madison and I had tried to keep our relationship going. After four months of growing frustration and drifting apart, she told me she had been asked out and was moving on.

"I told him about you and Madison. He said we would be different." Z crossed her arms. "It was really hard to break up with Brett. He loved me just as I was, with all my nerdy ways. He didn't want me to change. He wanted to keep doing the same things. I would have been happy..." Z let out a long sigh. "But I wanted to change."

I asked gingerly, "Will you see him this week?"

"No. The things I've enjoyed the most at school he probably doesn't want to hear about. He was a great guy for a certain time in my life, but I've changed."

"I'm glad you've changed. You're pretty cool to hang out with now."

"Thanks. Back to my guys. How did the movie-watching group come to be?"

"Landon, Rob, Dimitri, and I have always been friends. Over the summer, Dimitri came up with the idea of movie-watching nights in our room. I don't know what happened to Landon over the summer, but he had sworn off binge drinking when he came back. So, he was in. They asked Vivek to join as he tells lots of jokes. At the start of the year, Rob was still bartending at parties, but he was getting bored with it. When we kept telling him about how much fun we were having watching movies, he said he'd join us if he could do bartending for us. We agreed. And then Dimitri asked you to join."

"When Rob misses, is he bartending at a party?"

"Yes. When Landon or Vivek miss, they're hooking up with someone."

"But you never miss."

"If I said I was going to miss, would you go?"

"No."

"And if you're not there, my friends would be very disappointed. When you're comfortable enough with my friends to go without me being there, I'll start hooking up again."

We took a break from talking. After a while, I stopped at a convenience store so Z and I could use the bathrooms and buy some snacks. When we got back into the car, Z said, "I have a favor to ask of you. Let me give you the background before I ask it." Z took a big breath. "I told you that Katharine got kicked out of the cheerleader and football player clique. She totally deserved it. She enjoyed causing problems and starting fights by flirting with guys. But she was still a cheerleader; from what she says the most knowledgeable one. As much as the other senior cheerleaders may have hated her, they had to keep working with her."

"Sounds lovely." I was not a drama person, and this sounded like lots of drama.

"It was. You remember Giselle Parker?"

I nodded. "Classmate of yours. Very cute, with curly red hair and lots of freckles. Moved to our town just before her freshman year. Before I could strike up a conversation with her, she had a boyfriend. She dated him for two years. By the time I heard she had broken up with him, she had another boyfriend. She was still dating him when I graduated."

"She was the go-between between Katharine and the other cheerleaders. She's a caring, sweet person that Katharine always got along well with."

"Did she go to any of Katharine's cheerleaders-and-football-player parties?"

"I doubt it. She was very devoted to her boyfriend. And he was devoted to her. They dated past graduation and decided to stay together despite going to different colleges."

I decided to double back. "Did you know that Katharine had deserved to be kicked out of the cheerleaders-and-football-player clique?"

"No. I was oblivious to all the stuff. Katharine blamed Becki, and that was good enough for me. But after a while, I figured out that the only reason Katharine was teaching me all this stuff was for me to cause Becki grief by flirting with her boyfriend."

"Did you stop flirting with him then?"

"No. This will sound awful, but I was willing to do my best to hurt Becki if that was what it took to keep Katharine teaching me about guys. I was so sick and tired of getting nowhere with guys. When I told Katharine she was evil for pushing me to try to break up Becki and her boyfriend, she'd laugh and say it was true."

I rolled my eyes. As a no-drama person, that kind of stuff had no appeal to me. "And she's your best friend now."

"Yeah. When Becki's boyfriend told me that he knew what I was up to and that he didn't want to talk to me again, I assumed my tutoring from Katharine was over. But she said, 'Let's find another guy for you to flirt with'. Neither of us had had a close female friend in a while. Making the high school cheer team is very competitive, so Katharine always looked at her fellow cheerleaders as competitors. Dating for her was a competition with the other cheerleaders for star football players and guys with nice cars. I never competed with her. She liked showing off how much she knew to the smartest girl in school. She loves talking me into doing things I don't think I should do. It's almost a game now between us - she'll pitch some idea, I'll say no, and she'll eventually talk me into it."

"But she didn't talk you into whispering into Dimitri's ear that you were wearing the panties he gave you."

"She didn't really try. She can read me very well and knows when I'm willing to be convinced and when I'm not. She reads almost everyone well, which is why she's so good at flirting."

I could see why that'd be important. "Back to Giselle."

"Katharine has kept in touch with her. Two weeks ago, she broke up with her boyfriend and has been down ever since. I've been encouraging Katharine to be more empathetic, so she decided to do something over Thanksgiving to cheer Giselle up."

"That's nice of her."

"It is. It's going to be a sleepover at our house on Sunday night."

I wrinkled my brow. "Shouldn't it be at Katharine or Giselle's house?"

"Giselle's parents have heard enough stories about Katharine that Giselle doesn't think they'd agree to a sleepover with her. Giselle told her parents that I'm rocking all my classes right now and that I've helped her a few times with her homework. So, the sleepover is about getting to know me better and finding out how I do so well in my classes. Katharine's presence is never to get back to Giselle or her friends' parents."

"Okay. No threat from me on that."

"Also, Katharine has a plan that requires it to be at our house. Or maybe multiple plans. At least one of those plans requires your participation."

"Me?" I was surprised. "I've never had a conversation with Giselle."

Z raised her hands in a 'who knows?' gesture. "Katharine wants you available to be at the sleepover. She says she can't tell me what she's planning because Giselle is being wishy-washy. I think there's more to it than that." Z crossed her arms and frowned. "I hate asking you to write Katharine a blank check for Sunday night, but Giselle is a really nice person, and I'd like for Katharine to pull something off that lifted her spirits."

"Tell Katharine that I'll go along with whatever she comes up with." This was a no-brainer. An evening with Katharine AND Giselle? I'd be a fool to turn that down, even if I didn't know exactly what would happen.

Z said, "Thanks. I so appreciate you being such a good sport for my friend."

"No problem."

* * * *

Sunday morning, we had cinnamon rolls and orange juice for breakfast. It was a nice family meal. Z and I told our parents several stories from movie-watching parties. The alcohol and Z's flirting didn't get mentioned, but the jokes and camaraderie did.

I loved my parents. They treated Z and me as adults. They were proud of how well we were doing academically. They had high standards for us, but they weren't overbearing about it. Rather than tell us what to do, they'd tell us what they thought worked and what didn't, and let us make our own decisions.

After breakfast, Z and I got in my car. The doctor my mom worked for, Dr. Harrington, had hired us to take care of their dog Bart. Z said, "I got an update from Katharine. Giselle, Laurie Hughes, and Valerie Collins will be sleeping over."

"Laurie Hughes sounds familiar, but I can't picture her. I'm drawing a blank on Valerie Collins."

"Laurie was in several of my classes. She seemed nice. I can't tell you anything more about her. Valerie is a senior in high school. I don't know her."

"Okay."

"Katharine is going to give them a flirting workshop once Mom and Dad go to bed at ten."

"A flirting workshop?" I guessed I should have seen this coming. Katharine had enjoyed teaching Z to flirt so much that her teaching a flirting workshop made perfect sense.

"Yes. Giselle, Laurie, and Valerie will take turns flirting with you while Katharine and I watch. We will then advise them on how to flirt better. Katharine hopes that after watching me flirt with your friends so much, you'd know how to handle flirts. She wants you to be out of the house when the girls arrive and come home at exactly 10:30. Nothing is to be taken seriously. Everything that happens tonight is top secret and not to be discussed with people who weren't there. You are to be a perfect gentleman. Do you agree to all that?"

"Do I have a choice? If I don't agree, the workshop doesn't happen."

"No, you don't. You gave Katharine a blank check Friday, and she's cashing it tonight. Giselle really likes the idea of learning how to flirt. She feels unprepared for dealing with guys now that she's unattached. She's only dated her two boyfriends, and both times they were going steady after the first date. But though she likes the idea of learning how to flirt, she thinks she'll be uncomfortable flirting and seeing other people flirt."

"Sounds like a tough needle to thread."

"And you will have to thread it," Z said earnestly. "You will make or break tonight. Katharine says for you to be encouraging and to make it fun. She asks that you please put the fun of Giselle, Laurie, and Valerie in front of your own."

"Why does Katharine think I can thread that needle? I've talked with her some, but it's mainly been flirting with her before or after she studied with you. She's putting a lot of faith in me."

"I've told her lots about you. She likes how you've been so supportive of me, making flirting with your friends and movie nights fun for me. You like girls but aren't a horndog. You're good-looking, but not stuck up about it. You're very long-term focused, so you won't try to take advantage of a special party. As I said, you're used to flirting and know not to take it seriously. She said you're the only guy she'd feel comfortable making the star of a flirting workshop."

I smiled at all the praise. "Okay. I'll do my best."

* * * *

At nine, I went over to the Harringtons'. I took Bart on a long, slow walk, letting him stop and smell things to his heart's content. As I did, I thought about the flirting workshop; more specifically me and the girls at the flirting workshop. Wouldn't it be great if one of the girls at the flirting workshop became my girlfriend? This morning when Z and I had gotten home after taking care of Bart, we had pulled out her last yearbook to look up Laurie and Valerie. They both looked pretty, though not as pretty as Giselle and Katharine. Valerie played forward on the basketball team and was tall. I guessed that Laurie and Valerie were also unattached. A flirting workshop would be a great way to get to know several attractive girls.

I badly wanted a girlfriend. I badly wanted to be in love with someone. Regular sex would be nice, but it wasn't my top priority. I had loved being in love with Madison and having her be in love with me. It made me feel on top of the world. I hadn't felt that way since she moved away.

"What do you think, Bart? Could one of the girls at the workshop become my girlfriend?"

Bart didn't seem to think much of the idea. Sadly, I had to admit he was right. None of them went to the same school as me, I didn't want a long-distance relationship, and there wasn't enough time during this break to even start a relationship.

If I was going to have a girlfriend, it'd be one of my fellow pre-med majors. But it was very risky to get emotionally involved with a pre-med major. So many pre-med majors wouldn't make it, and it was painful to watch those who weren't quite good enough slowly admit defeat. My roommate my freshman year had been a pre-med major, full of confidence that he'd become a doctor one day. We had hit it off and had spent most of our free time together. But as we had progressed further into chemistry, he had struggled more and more. "Struggle" isn't the right word - he had been good at chemistry, but you had to be great at it to make it as a pre-med. I had given him some help, but I hadn't been able to spend a lot of time helping him as I had to keep on top of all of my classes. He eventually admitted defeat and changed majors. I didn't see him anymore. If Dimitri hadn't stopped his binge drinking, I wouldn't see him anymore. Any of my fellow students at any time could run head on into the one required subject that they aren't great at and be forced to give up their dream. Or they could crack under the stress. Or burnout. It was best for me to not get too close to anyone, for fear that if they went down, they'd take me with them.