“Cheers, man,” Jack raised his drink to Tyler. The two men were sitting at the popular Irish bar around the corner from Katie and Tyler’s office, surrounded by the after-work crowd enjoying their $3 happy hour drafts.

“What are we cheers-ing to?” Tyler asked.

“Your long career,” Jack answered, confidently.

“I like the sound of that,” Tyler grinned, and clinked his glass against Jack’s. They both took a long gulp of their beers.

“Thanks again for making the time. I know we just met--” Tyler started.

“Like I said,” Jack interjected, “anyone who does Katie a solid is a friend of mine. And she hasn’t stopped talking about you since you started, so I figured this was a good chance to get to know each other.”

Did Tyler pick up a hint of suspicion in Jack’s voice, or was he being overly sensitive? Tyler had tried to keep things professional between himself and Katie. Although he’d be lying if he said there wasn’t some kind of weird attraction there…not that he’d ever act on it.

“Well, thanks--like I said, I owe her for taking a chance on me. But you know, I’d love to hear more about your journey. How did you get where you are? Take me through it,” Tyler deftly steered the conversation back to Jack. 

“It’s kind of a long story,” Jack started. “Although the short version is, I grew up pretty poor. I was the first in my family to go to college, which I was only able to do on a combo of studying my ass off and a rugby scholarship.”

“Oh wow,” Tyler was genuinely surprised. “You’re so accomplished. I had no idea you were...a college athlete. Do you still play?” 

“Not really,” Jack laughed a little. “My body isn’t what it used to be. I spend more time at the law firm than the gym nowadays. But I was playing on a weekend club team for a while. I figured out it was a good way to network.”

“What do you mean?” Tyler asked, curious.

“The guys in the firms around here all like to blow off a little steam,” Jack explained. “And I’ve never really been into the club scene, so I found my tribe on the field. Met a guy through playing for fun who ended up introducing me to my first boss.”

“You make it sound so easy,” Tyler said in admiration.

“I mean, not to sound like a jerk, but isn’t it...easy for you, too?” Jack tried to ask in the least offensive way possible. “To be honest, with your name, and connections, and...family income, you could have any job you want, right?”

Tyler took a beat. His family was a button to press, for sure, but he knew Jack didn’t mean anything by it. It’s what everyone thought, not just Jack.

“Yeah, I suppose that’s true,” Tyler said slowly, “but I don’t want to owe my family anything. It’s really important to me to make my own way. Like you.”

“I get that,” said Jack. “It’s a good feeling to know at the end of the day that you earned everything you have--and the people in your life are there because they want to be.”

Tyler added, “Exactly. It’s why I mostly keep to myself--I can never know for sure who’s trying to be around just because of... my last name.” 

Jack saw a flash of loneliness in Tyler’s eyes. He threw his arm around the intern’s shoulders.

“Well I don’t care who your family is,” Jack said. “And the next round’s on me.”

***

They were several beers deep when the subject of Katie came back around. Both men obviously had a deep affection for her, although neither of them knew that Tyler’s feelings had longer roots.

“So I’ve got to ask,” Tyler said to his new best friend, “why aren’t you and Katie married yet? I know if I was with the right girl, I'd propose stupid fast.”

Jack sighed a little. “So I’ve definitely been thinking--a lot--about proposing--”

“That’s great, man!” Tyler clinked his glass against Jack’s, a little too enthusiastically, spilling a bit of beer in the process.

“I love her so much,” Jack continued, “and I want to spend my life with her. No question. But…”

“But what?” Tyler asked.

Jack felt a little guilty talking about his relationship, but it also felt good to get someone else’s opinion. Plus, alcohol always made the truth flow easier. 

“She doesn’t believe in marriage. When we talk about it, she shuts down. I get the feeling that something...bad...happened in her past to make her feel that way, and I don’t want to pry if she doesn’t want to share.” 

“Well, what has she said about it?” Tyler loved trying to solve a problem.

“Not much, really, just that she doesn’t think that marriage is made to last--probably because her dad left when she was still a kid. She says she’s happy with the way things are. She doesn’t want to ruin it.” Jack gave a shrug as he downed the last of his current drink. “I keep hoping I can change her mind.”

Tyler thought for a beat. “Oh man, that’s hard,” he started. “I mean you have to respect what she wants,” Tyler downed his drink too. “But there are two people in the relationship--what you want matters too. I guess for now, just be honest about your feelings and take it from there.”

The two men sat for a beat, lost in their own thoughts. Jack checked his watch, surprised.

“Oh wow, I didn't realize how long we’d been here,” Jack said. “I told Katie I’d pick up dinner for us, and now I’m late. Sorry, I’m going to have to run.” Jack made a sign to the bartender he was tabbing out.

“No worries--and hey, thanks again so much. Are you sure I can’t throw in, for that last round, at least?” Tyler offered.

“Absolutely not. My pleasure--and you’ll get me next time.” Jack answered, signing the bill.

“Yeah, I’d like that,” Tyler said, genuinely pleased. “I still have so many questions.”

“Well, I don’t have all the answers, but we all need people in our lives we can trust,” Jack said, gathering his jacket.

“Tell Katie I said hello,” Tyler said as they exited together, each pinging an Uber.

“I will,” Jack said, “And thanks for your advice, too. I’d appreciate it if you kept it between us.”

“Of course,” Tyler said. 

“Thanks, man.” Jack pulled Tyler into a bear hug. “You good?”

“Yeah, for sure,” Tyler answered. “Jack, I’m really glad I met you. I... don’t have a lot of friends.”

“You do now,” Jack gave him a warm nod and bounded to the car waiting to take him home. 

Tyler watched him go, conflicted. As much as he liked Jack, he couldn’t help wishing he was the one taking dinner to Katie instead.