Logan took his coffee and muffin to a small table near the window, feeling a quiet rush of satisfaction. One down, four more to go.
Even though the conversation was short, it was real, and he kept eye contact the whole time without it feeling forced or awkward. He might not have to work as hard as he thought.
He was halfway through his muffin when an older woman came up to his table. Not old, but mature, maybe in her late thirties or early forties, with the kind of graceful aging that made it look like she took care of herself. She wore yoga pants and a fitted jacket, carrying a water bottle and a yoga mat under one arm.
"Excuse me," she said, gesturing to the empty chair across from him. "Do you mind if I sit here? There is no room anywhere else."
Logan looked up and saw her eyes. They were a very bright green that was sharp and looked at things. "Ah, of course, go ahead."
She sat down with her own coffee, setting her yoga mat against the table leg. "Thanks."
"On the weekends, this place gets wild. I usually come earlier, but I slept in today, hahaha..."
"Bad night?" Logan asked, keeping his eyes on her. Most people probably thought her look was scary because it was direct and confident, but he didn't look away.
"More like a rough week because work has been a nightmare." She drank some coffee and looked at him over the edge of her cup. "You seem familiar... is there any chance you go to the gym on Fifth Street?"
Logan said, "I mostly run and do calisthenics at home. Well, it's probably less expensive than a gym membership."
"Smart way of thinking. I wish I could be that disciplined."
"I make excuses if I don't have the structure of a class." She smiled, and her face showed that she liked what she saw. "You've obviously been putting in the work, though. Not many people your age are that dedicated."
They talked for a few more minutes about their fitness routines and the neighborhood, and Logan never looked away. She looked almost impressed, like she wasn't used to younger guys being able to look her in the eye without getting nervous or awkward.
She finally got up to leave and pulled a business card out of her jacket pocket and slid it across the table. "By the way, I'm Jennifer Lawrence. I own a marketing company in the city."
"Feel free to get in touch if you ever need a job or want to make connections."
Logan took the card and looked at it for a moment before looking back at her. "Oh, um, I'm Logan Hart."
"Thanks for this, I really appreciate it."
"Good to meet you, Logan. Maybe I'll see you later."
[Mission status: 2 out of 5 completed. Great job. You're gaining speed.]
Logan put the business card in his pocket and finished his coffee. With each conversation, he felt more and more sure of himself.
He had already done two and had three more to do. He chose to go somewhere else, maybe to look at some stores or find another coffee shop. It seemed like staying in one place would make it harder to naturally have more interactions.
He walked through a bookstore a few blocks away and looked at the shelves without really wanting to buy anything. That's where he met the third woman, a college student with thick glasses and many books in her arms.
She was having trouble getting to a book on the top shelf. She was standing on her toes and stretching, but it didn't work, and that's where Logan stepped in. "Excuse me."
"Do you need help?" Logan asked as he walked over.
She turned around, looking shocked at first, then relieved. "Oh my god, yes please."
"I don't understand why they put the good books so high up."
Logan quickly took down the book she had been trying to get and gave it to her. She smiled and thanked him as she took it. When their eyes met, he held her gaze.
"Thanks a lot... The shelves in this store are too high for me."
"Not a problem. By the way, what are you learning?" Logan nodded at the pile of books she was holding.
"Psychology. I have a midterm next week, and I'm really behind on my reading." She moved her glasses around while still looking at him. "Are you in school?"
"Actually, I'm starting college in a few weeks."
"Oh great! What is your major?"
They quickly started talking about classes and life on campus, and Logan was genuinely interested in what she had to say. She spoke clearly and was funny, making fun of her bad habits of putting things off and the horrible subject of organic chemistry.
He looked her in the eye the whole time, and she seemed fine with it, even leaning in a little as they talked. She looked at her phone after about ten minutes and winced.
"I should probably leave now. I still need to eat lunch before the study group starts in twenty minutes."
Logan said, "Good luck with your midterm."
"Thanks... oh! And... uh..."
"Hm?"
"Do you... h-have Instagram or something like that? I know a few people who are starting college this year."
"I could show you how to use the group chat and help you get set up before class starts."
Logan took out his phone, and they talked to each other. She smiled at him one last time before going to the register, and he saw her look back at him once before she turned the corner.
[Mission progress: 3 out of 5 done. You're doing an impressive job. Do you see how each interaction becomes easier? That's building confidence in real time.]
The system was correct. Logan felt more at ease and less tense now.
The nervousness that had been there at first was going away, and in its place was something that felt almost like fun. He was really talking to people and connecting with them in small but important ways, like it didn't feel forced or fake.
The fourth interaction happened at a clothing store. Logan had come in without a plan, just to look around and kill time while he looked for chances. A woman's voice came from behind him while he was looking at a rack of shirts.
"Those would look good on you."
He turned to see a lovely girl his age, maybe in her early twenties, with long dark hair and a smile that made her look confident. She had a few things draped over her arm, which made it clear that she was shopping for herself, but she didn't seem shy about giving fashion advice to people who didn't ask.
Logan looked into her eyes and smiled. "You really think so?"
"Of course. The color would look good with your skin tone, and the fit looks like it would work with your body type." She moved in closer to look at the shirt he had been looking at. "Do you know how to dress, or are you just here to find out?"
"Somewhere in between," Logan said, keeping his eyes on Logan's the whole time. "I know what works for my body type, but I'm always open to what experts say."
"Expert might be too strong of a word, but I've been shopping long enough to have opinions." She took a different shirt off the rack and held it up to him. "This one... and... oh! This one is for sure! The navy makes your eyes pop."
For the next fifteen minutes, they talked about fashion, fitness, and other things that came up naturally. She was fun to talk to and flirty without going overboard. Logan liked the back-and-forth of their conversation, how it moved from one topic to the next without any awkward pauses.
At one point, she touched his arm, which was a casual gesture that lasted a little longer than it needed to. "You know, it's a breeze to talk to you. Many guys get weird when a random girl tells them how to dress."
Logan said, "I appreciate good advice when I hear it," and he didn't take his eyes off of hers. "Plus, this is a lot more fun than shopping alone."
She laughed. "Hehehe, glad to hear it."
"Hey, you should give me your phone number."
"I'm always on the lookout for a shopping partner who can talk to me."