The Rules of Dating a Younger Man

The following Tuesday night, I was over at Owen’s brownstone back in the City. He and Devyn had invited me to have dinner and catch up. This was probably only the third time I’d been over to his new place. The aroma of seafood and onions cooking on the stove swirled around me in the living room as Owen and his fiancée worked in the kitchen to prepare the meal.

Devyn’s teenage brother, Heath, sat on the couch opposite me. His sister Hannah was in her room doing homework. Devyn’s siblings technically lived with their mother, but my understanding was that they were at Owen and Devyn’s the majority of the time. They each had their own room here, too.

Heath stood and moved closer to show me something on his phone. “Hey, remember this?” He faced the screen toward me, revealing the video he’d taken of me and Alex kissing against the building the time she’d visited Manhattan. My chest tightened. It was painful to watch—especially after this past weekend. But damn. That was some memory. I’d been so into her that day.

Devyn’s brother was known for posting shit on the Internet, and several of his videos had gone viral. Owen had warned me that Heath had this footage, but Heath had never mentioned it to me before now.

“I do remember that day, yeah,” I finally said once I’d managed to pry my eyes away. “And I’d prefer you erase it from your phone.”

“Why would I do that?” He smiled. “It’s too much fun being able to threaten you with it.”

“There are much more interesting things than two people kissing on the street. People aren’t going to care about that.”

“You don’t think this would go viral?”

“I would hope not.”

He shrugged. “Only one way to find out.”

“Please don’t.”

“If I add some interesting music or a funny caption to it, it might do well. Plus, chicks love sappy kissing stuff like this.”

I gritted my teeth. “Can you please…not?”

Heath crossed his arms. “How much you gonna give me if I don’t post it?”

“If you don’t post it, I won’t tell your sister you’re trying to extort me. Pretty sure she wouldn’t be too happy if she knew.”

“She already knows how I operate. Heck, I’ve threatened her. She still loves me.” He laughed. “The other day she was singing in the shower, and I recorded it from behind the door. Her voice could kill the birds outside. Saving that one for collateral.”

Begging wasn’t going to stop this kid. I had to try a different route. “I know you’re pretty young, but have you ever had your heart broken, Heath?”

He looked away, seeming to ponder. “Yeah. Once.”

“When?”

“When I was in middle school. There was this girl, Ava. She’s my friend’s sister. She sort of made me think she liked me, and then did a total one-eighty. I don’t really want to talk about it.”

“Oh, you don’t want to talk about it? Because it sucked, right? So why relive it?”

“Right.”

“Okay, well, imagine if on top of everything else, I had some video of you kissing Ava. And I threatened to plaster it all over the Internet—not only for you to see, but everyone else, too. Then every time you saw it, you’d have to think about how things had turned out between you and her. How would that make you feel?”

His smirk faded, and he exhaled. “That woman in the video broke your heart?”

“It’s a long story, but we’re not together anymore. And that thing going viral—or even a hundred people looking at it—would really suck. It’s not that I don’t want you to have your fun or grow your following. And I can normally take one for the team and laugh at my own expense. But that video? I don’t want to see that ever again, let alone a million times.”

Heath hung his head. “Damn. Now I feel bad.”

I arched a brow. “Bad enough to delete it?”

He narrowed his eyes. “I don’t know.”

I reached for my wallet. “How about bad enough to delete it with twenty bucks?”

He scratched his chin. “Fifty makes me feel particularly bad for you.”

“Done. But I need to see you get rid of it myself.”

I watched as he deleted the video.

I pointed to his phone. “Go into your deleted files and remove it from there, too.”

He sighed but did as I asked.

I reached into my wallet, took out a crisp fifty, and handed it to him.

Heath smiled. “Nice doing business with you.”

“I sure as heck hope you can put that ballsiness of yours to good use someday.”

Devyn walked into the living room. “What did my brother do now?”

“Nothing.” I slipped my wallet back into my pocket. “He’s good.”

She flashed him a skeptical look before announcing, “Dinner’s ready.”

“Thanks, Dev.”

I walked into the kitchen to find Owen at the table feeding their baby boy, named Devon after Devyn—same pronunciation, different spelling.

Owen looked up from the small jar of sweet potatoes he was feeding Devon. “So, how was your weekend in the Hamptons?”

I’d told Holden I was going to the Hamptons and never clarified the change in plans. He must have told Owen. I shook my head as I took a seat next to him. “I didn’t end up going.”

His eyes widened. “You chickened out?”

“Not exactly.”

I filled him in on the Ryan’s House project resuming, canceling on Lacey, and finished up with my intense encounter with Alex in Seneca Falls.

Owen scraped the bottom of the glass jar with a spoon. “So, you told her you’re seeing someone else?”

“Yep. I kind of had to when she saw the name pop up on my phone.”

“That’s not true. You could’ve lied.”

“What’s lying going to achieve at this point? It’s not like Alex and I have a chance. There was no reason to hide anything.”

“So that’s good that she found out, right? Don’t you think it will help you both move on?”

“Well, Alex isn’t currently seeing anyone, so not sure how much this is going to help her. It certainly didn’t help me move on when I thought she was seeing someone else. It just made everything harder to swallow.”

“How did you leave things with her?”

“She looked hurt after I admitted I was seeing Lacey. She went quiet after that, and I let her be. There wasn’t anything I could do to make the situation easier. If I’d told her my feelings for Lacey were nothing compared to how I still felt about her?” I shook my head. “I can’t be around her without wanting to reach out and touch her, either.” I rubbed my temples. “It’s so damn hard.”

“You never saw each other besides at the house?”

“Well, just for a minute at the bar that one night. We worked at the house during the days and went back to our respective hotel rooms.” I looked away. “She was hurt. And it was hard to see that. But if she’s not going to change her mind about us, maybe it is better if she thinks things are more serious with Lacey than they are.”

“Speaking of that, what is the deal with Lacey?”

“Well, I agreed to go to the Hamptons with her when I thought Alex had moved on, because I was forcing myself to do the same. Now I’m not sure what the deal is, but Lacey and I are gonna see each other tomorrow night.”

“So you’re not really ready to go there with her.”

“I need to take it one day at a time. I got the email about the project resuming right after I’d told her I would go away with her.” I sighed. “The timing of that was kind of strange.”

“Definitely,” he agreed.

“Was that fate? I don’t know. I have some thinking to do—though not about Alex. Because nothing has changed there. More about how long I can string Lacey along before she kicks me to the damn curb. I also don’t want her to get hurt.”

“Who would’ve thought you’d become so damn conscientious?” He patted me on the shoulder. “I’m proud of you. You could’ve taken advantage of the situation—used Lacey for gratuitous sex and Alex would’ve never known.”

“It needs to feel right, you know? It hasn’t yet.”

“My boy is growing up.”

I shook my head. “’Bout time at thirty-one.”

***

The following evening, Lacey and I were headed to dinner in the West Village after meeting for coffee first. We walked hand in hand down the street. She’d picked a restaurant I’d never heard of, so I was unsure where we were heading both literally and figuratively now.

I really liked her as a person, and under different circumstances, I’d bet we would’ve stood a real shot. But more times than I could count tonight, my mind had returned to the look on Alex’s face when I’d told her I was seeing someone. And that had me distracted, unable to give Lacey my all.

“I’m sorry again about missing the Hamptons trip,” I said as we strolled.

“No biggie. Your work upstate is important.”

“Thanks for understanding. We’re getting to the end of the project, and it’s gonna be nice to finally see it finished. What’s the point of all that work if we can’t complete it, right? I’m really grateful, but I still can’t believe they reinstated our permit.”

I’d told Lacey before that the woman I’d been involved with also volunteered in Seneca Falls, so I was expecting her to ask whether I’d seen Alex this past weekend. But she never did, and I certainly wasn’t going to offer that information.

“Tell me more about your trip,” I finally said, happy to change the subject.

“Have you ever played pickleball?” she asked.

“I haven’t, but it seems to be all the rage lately.”

“I played a couple of times while I was there,” she said. “It was so much fun, like a cross between tennis and ping-pong.”

“I feel like I’m hearing about it left and right. I might need to try it.”

“That’s definitely a sign you should try it. It’s actually been around since the sixties. But it’s only gotten popular recently. Don’t laugh, but I think I’m gonna join a pickleball club here in the City.”

“Why would I laugh at that? Because it’s the modern-day version of a bowling league?” I knocked into her playfully.

“That’s exactly what it is.” She giggled. “And I’m not even ashamed.”

“You shouldn’t be. Anything to blow off steam.”

“I’m not doing much else to blow off steam lately.” She winked.

Ugh. There it was. The elephant in the room. The fact that I hadn’t initiated sex yet, while she’d made it clear more than once that she was down to have some fun with me. She wasn’t even asking for a commitment. Was I crazy not to jump at the chance?

I pretended I didn’t get her innuendo and pushed forward. “So, besides pickleball, what else did you do?”

Lacey told me more about her trip until we finally got to the restaurant, an Asian-fusion place that had been recommended to her by a co-worker. The food was perfect. The ambience was perfect. Everything was perfect except for the fact that I still didn’t know how to approach the evening once we left this place.

I had officially reached the shit-or-get-off-the-pot portion of this courtship. It wasn’t fair to keep playing dumb when Lacey had been nothing but clear with me this entire time. So as we exited the restaurant, I decided to make the first move for once. “We’re closer to your place than mine,” I blurted.

“I was thinking that myself.” She batted her lashes. “Are you saying you’d like this night to continue?”

“Well, it’s too late for you to teach me how to play pickleball, but I’m sure we can find something else to do.”

She beamed. “I think we can.”

That was it. I was going to do it. There was no way I could back down now—because that would be fucking rude. My stomach was in knots as we hopped on the subway and headed toward her neighborhood. I tried to convince myself it was something I’d eaten, rather than my lingering uncertainty.

When she opened the door to her place, I realized Lacey had a tiny apartment. It was one of the smaller studios I’d seen in the City.

I looked around. “This is…”

“Small.” She laughed.

“How do you fit all your stuff?”

“I’m sort of forced into minimalism. My couch turns into a bed, and then there’s storage underneath.” She blushed. “Don’t worry. There’s plenty of room for two.”

“I wasn’t too concerned.” I laughed nervously, feeling like an inexperienced teenager. I didn’t even recognize myself right now. I was the same guy who’d fucked Alex into oblivion against a hotel room wall, and yet with my nerves right now, you’d think I hadn’t had sex in years.

I can do this.

It’ll be good for me.

I need to move on.

Before I could think any more, Lacey had wrapped her hands around my face and brought me in for a kiss. I opened my mouth and let her tongue in. She pressed her little body against mine. My heart began to race. She could probably feel it, and she would likely misinterpret the reason.

You’re doing this.

You can’t stop it now.

My heart beat even faster as she led me over to the couch and pulled me on top of her. I willed myself to kiss her faster, to feel more, to get into it. But the faster and deeper I kissed her, the more forced it felt. My body was tight, and everything was stiff—except my dick. She moved to sit on top of me.

How could I not be hard right now? I had a beautiful woman straddling me.

Then Lacey lifted her top over her head, revealing her black satin bra.

It felt like a virtual timer had been set. Past experience told me I didn’t have too much time before I’d be expected to stick my dick inside of this woman. And considering my dick seemed to be taking a break tonight, that was a problem. The larger problem, however, was the realization that even if somehow my dick were able to get hard, this didn’t feel right.

I shut my eyes, and all I could see was Alex. Her blond hair. Her eyes, filled with concern the last time I saw her—concern that perhaps I’d moved on and found someone else. That couldn’t have been further from the truth.

I sat up under Lacey. Panting, I swiped the back of my hand across my mouth. “I’m so sorry.”

“What’s wrong?”

“It’s not you. God, you’re beautiful, and smart, and charismatic…”

Her expression dampened as she figured out where this was going—nowhere.

“The problem is…I’m still in love with someone else. As much as I don’t want that to be true, it just is.” I paused. “I saw her this past weekend at the worksite, and it made me realize my feelings are as strong as they always were. She and I aren’t together, but I can’t shake her.” I looked into her eyes. “I thought I could move on with you tonight. I’m so sorry I can’t.”

Lacey’s expression was hard to read, a mix of sympathy and disgust. “I don’t know what to say, Brayden, except I’m glad you stopped things when you did. Because while I don’t mind sleeping with someone who’s getting over a breakup, wasting my time on someone who doesn’t even want me is a whole different story.” She sighed. “I hope you can get her back, if you can’t move on.”

I’m more likely to end up alone.

And that would be exactly what I deserved.

I stood and adjusted my shirt, shaking my head. “I must be crazy for walking away from you.”

She closed her eyes and bent her head back in frustration. This girl had already been hurt by her ex, and I’d hurt her again. I felt sick. Lacey deserved the world, but I wasn’t going to be the one to give it to her. So the sooner I got out of her sight, the better.

I left awkwardly and vowed never to do this again. I needed to be absolutely sure I wasn’t wasting someone’s time before I got involved. Walking down the street as I left her apartment, I’d never felt so alone. Not only did I not have Alex, I was incapable of making a connection with anyone else. I wanted to call someone, but it was late, and I didn’t want to disturb the kids by calling any of the guys.

A few minutes later, though, my phone rang. Owen.

“Hey, man,” I answered.

“Everything okay?” he asked. “I just thought I’d check in. Wanted to see if you ended up going on that date.”

“It didn’t go well.” I exhaled, my voice shaky. “I know it’s late, but…what are the chances I could steal you away? I’m all fucked up. I could really use a drink and a friend.”

He hesitated. “Brayden, I’ve known you most of my life, and this is the first time you’ve ever asked me for a damn thing. Name the place, and I’m there.”

I asked Owen to meet me at a bar midway between his brownstone and the building. Once he’d agreed, I caught a cab. He’d texted me that he was there while I was still on the way, so when I walked in, I expected to see him sitting in the corner alone.

But instead, there were three: Owen, Colby, and Holden.