The Rules of Dating a Younger Man

“So, what’s new?”

I stirred the pot of sauce on the stove. “I think I overcooked the pasta. Though I suppose that’s not new, is it?” I pointed to the cabinet next to my stepdaughter. “Can you grab the strainer for me, please?”

Caitlin took the metal strainer out and placed it in the sink. Grabbing the potholders, I walked over and dumped the pot of angel hair. I’d made her favorite meal—meatballs and braciole. She usually came early and helped me cook, but tonight she’d worked later than usual. Together we brought everything to the table, and before I sat, I refilled our wine glasses.

“What did you do last weekend?” I asked, filling her plate with pasta.

“Friday night I went out for drinks after work and…I met someone.”

“Really? Tell me more.”

She smiled from ear to ear. “Well, his name is Justin. He’s a few years older than me. He’s never been married and doesn’t have any kids, but he wants them. And he’s handsome and sweet. Oh, and he’s an orthodontist.”

“Oh my. That all sounds fantastic. Especially the sweet part.”

Her eyes sparkled. “We went out Saturday night and Sunday night, too.”

I couldn’t remember the last time Caitlin had sounded so excited about meeting a man. It made my heart full. “I can’t wait to meet him.”

“I told him all about you, and he can’t wait to meet you, either.” She rested her fork on her plate. “This might sound weird, but something about him reminds me of Dad. He’s just sort of doting and goofy.”

My eyes welled up. “Your father was definitely both of those things. I’m so happy for you, Caitlin. He sounds amazing.”

She cut into a meatball. “What did you do last weekend?”

“I actually wound up going to Seneca Falls. The missing permits that had stopped work on the Ryan’s House project came through, so things started back up again.”

“Oh, wow. Did you see Brayden?”

“Yes, he was there.” I tried to keep my face impassive, but I guess I failed.

Caitlin sighed and set down her fork. “I don’t understand why you’re torturing yourself. I told you I’m okay with it. And I am. What happened between Brayden and me was a long time ago. We were just kids, really.”

“I know, but…” My eyes welled with tears. “It doesn’t matter anyway. He’s moved on. Brayden’s dating someone.”

She frowned. “Oh no.”

“It’s fine. Really, it is.”

“Is it serious?”

I shrugged. “I didn’t ask.”

Caitlin wiped the corners of her mouth with her napkin. “Maybe he just told you he’s seeing someone to make you jealous? A last-ditch effort to get you to change your mind?”

I shook my head. “I saw her name come up on his phone when she called. The only reason he told me about her was because I asked when I saw it.”

It was my stepdaughter’s turn to sigh now. “Alright, well, I’m sure he’s only moved on because you cut things off with him. It might not be too late. Tell him how you feel. I want you to. I told you, I reacted the way I did because I was shocked. It was immature and brought back old feelings of the silly competition I used to have in my head with you. But I know we’re not competitors.” She rested her hand on my arm. “You’re my biggest cheerleader, Mom. You could never be a competitor.”

I smiled sadly. “Thank you for saying that. But I’m moving on. I think it was just seeing him for the first time after a few months and finding out he’s with someone that made it hard. It will get easier.”

Caitlin gave me the side-eye. “I don’t know about that. I hope you know I’m being sincere when I say I want you to go after this.”

“I do, sweetheart. And I appreciate that.”

She swirled pasta around her fork. “But…if you’re really moving on, that means you have to put yourself back out there. Have you joined any dating apps or anything?”

“Not yet.”

She frowned. I didn’t want her to worry, so I shared something I thought might make her feel better. “But I did get asked out recently.”

Her eyes lit up. “You did?”

“Wells’s boyfriend has a brother. His name is Everett. The four of us had dinner one night, and at the end of the evening, he asked me on a date.”

“Excellent. When are you guys going out?”

“Soon,” I fibbed.

“Maybe we can double date with my new guy!”

I smiled. “That would be weird. But fun.”

We managed to not talk about Brayden for the rest of dinner, but thoughts of him were never far from my mind. After Caitlin left, I curled up on the couch with a blanket and flicked on the TV, but after a while, I picked up my phone and started scrolling through social media. I’d been staring at the screen, yet somehow not really paying attention to the photos until one hit me like a freight train.

Brayden. Holding a baby.

My heart pounded. He hadn’t been dating this new woman long enough to have a child, yet I couldn’t help but think how I’d feel if he did.

Brayden. A dad.

He’d make a great father, that much I knew. I’d witnessed his tenderness and parental skills with the kids he visited at the hospital. I imagined he’d be a hands-on dad, too—the kind who wore a baby carrier on his chest and went to Mommy and Me classes. He’d make up silly songs and let the kid eat a whole cake with his hands. Picturing it made me smile, until I remembered Brayden’s baby would have to belong to another woman. Then it became hard to breathe.

I scrolled down and read the caption. He’d been tagged by Owen. Uncle Brayden does his first diaper duty. Next time, he might not even put it on backwards!

It made me sad to think I’d never have any of those firsts. When Richard and I had married years ago, he’d already had a vasectomy. I’d never felt like I missed out because I had Caitlin. And she and Richard were always enough. But seeing the photo of Brayden holding a baby made me yearn for a child.

I stared down at the phone for a long time before finally forcing myself to swipe away. I was just lonely. I didn’t really want a child. The picture was a stark reminder of how different my and Brayden’s lives were. We were in such different places. He’d get married, have three, maybe four kids, and probably a dog and a pet goldfish. Whereas I had…my work.

I swallowed and forced myself to keep scrolling. Just like before, I wasn’t really looking at the photos, at least not until another one stopped me in my tracks. This time it was Everett—Wells’s boyfriend’s brother.

He was at the beach, standing in front of a volleyball net, mid-jump as the ball came toward his raised hand. It was impossible not to notice his six pack. Brayden’s was more like an eight pack. But I forced that thought from my head and pinched the screen to zoom in on his face. Everett was smiling. Having fun. Living life. Unlike me, who had been sitting home practically every night for the last few months, moping.

I attempted to swipe away more than once, but each time something stopped me.

Maybe it was time.

Time to move on.

Brayden had. The only way to get on a new path was to take a first step. And what better way to do that than with someone I’d already met? That would definitely be easier than meeting a stranger on a dating app. Plus, Everett was nice. And handsome. So I took a deep breath, swiped over to my text messages, and scrolled down until I found the chain where we’d exchanged messages a few times. I nibbled on my nail as I considered.

It had been three weeks now, and I’d never answered his last message asking me to dinner.

Could I just message him again out of the blue?

Should I?

Yes, yes, I absolutely should.

Brayden’s moved on with Lacey.

It was time. Long past time.

So I tapped out a quick text before I could reconsider.

Alex: Hey. Sorry it took me so long to respond. But if the offer is still open, I’d like to have dinner sometime.

I forced myself to hit send.

There. I’d done it. I’d moved on. At least I’d taken a big first step.

Maybe he wouldn’t answer. Maybe Everett was already seeing someone himself. But I’d done it. I’d put myself out there.

Less than a minute later, my phone buzzed.

Everett: Hey! Great to hear from you. How about tomorrow night?

***

I was a nervous wreck. Sitting at the bar waiting for my date, I looked around. The woman a few seats down was wearing jeans. Was I overdressed? I’d put on a little black dress, thinking that was a safe bet. But now I wondered if I should’ve gone with jeans—or at least worn flats instead of these heels. God, I’m so out of touch. Maybe I should go home and change…

But a minute later, Everett walked in looking frazzled. “Sorry I’m late. I got rear ended on my way here.”

“Oh my gosh. Are you okay?”

He nodded. “Yeah, just a dent. But we had to exchange insurance information and stuff. Last time I had a dent, it cost me almost four grand for a new bumper. What happened to the days when they just popped out dents and repainted? Now they replace everything.”

“I know. I feel like even appliances are disposable these days.”

He leaned in and kissed my cheek. “Anyway. I’m sorry to keep you waiting. Have you been here long?”

I pointed to my empty glass. “Long enough to calm my nerves the old-fashioned way.”

He smiled. “What are you nervous about? We go way back. It’s been what, like three weeks now?”

I smiled back. “We’re practically childhood friends.”

“Plus, I’ve been warned to be on my best behavior. Winston might be younger, shorter, and skinnier, but that guy fights like a ninja. I’ll swear I never said it, but he could kick my ass.”

I couldn’t imagine that to be true, but Everett’s self-deprecating humor put me at ease. “He and Wells are really cute together,” I said. “I can’t remember the last time I saw Wells check his phone so often and smile—except maybe when his favorite Real Housewife announced she was getting divorced. Then he was scrolling gossip for weeks.”

Everett laughed and gestured toward the hostess station. “You want to see if our table’s ready?”

I got up. “Sure. I told her I was here when I walked in, and she said to let her know when you’d arrived.”

He looked me over and shook his head. “Wow. I know I’m supposed to be on my best behavior, but can I say you look freaking amazing?”

I blushed. “Thank you.”

Once we were seated, Everett asked if I liked red wine, and when the server came by, we decided to share a bottle. He folded his hands on top of the menu. “So…I was surprised to get your text. Happily surprised, but surprised, nonetheless.”

I took a deep breath and nodded. “I’m sorry it took me so long. I was…” I considered lying and saying I’d been busy or traveling, but I didn’t want to start out on the wrong foot. So I was honest. “I was getting over someone.”

He nodded. “Well, his loss and my gain. And I appreciate that you took your time and made sure you were ready.”

I felt a little guilty because I wasn’t actually sure I was ready. In fact, I was starting to question whether I’d ever feel ready to move on from Brayden. But there was a limit to what I thought I should share with my date. So I smiled and lifted the menu. “I’ve never been here before. What are you going to have?”

“This is actually my first time here, too. I have this dumb rule that the first time I go on a date with someone new, I go to a place I’ve never been. I think it’s nice to start fresh and not have a memory of someone else lingering.”

I smiled. “I love that.”

The waiter brought our wine and poured. Everett held his glass up. “To something new?”

“To something new.” I smiled again.

Conversation came easily, and Everett told me how he’d gotten into the furniture business. I told him all about the spa I owned with Wells. Things couldn’t have gone much better. Everett was the full package—handsome, independent, divorced with a good relationship with his ex and his kids. If I were making a pros and cons list, there wasn’t much I could think of to put on the con side. Except for the big one: He isn’t Brayden.

But even so, it turned out that a hundred things on the left side of the list couldn’t offset that single thing on the right, no matter how hard I tried. After we finished dinner, Everett walked me to my car.

“I had a really good time tonight,” he said.

“Me, too.”

“Do you think you’d like to do it again sometime?”

It would’ve been easier to say yes and make up an excuse later. But Everett was a nice guy and deserved honesty. Plus, he was Wells’s boyfriend’s brother. I smiled and met his eyes. “Earlier, when you went to the men’s room, I was thinking about what a great guy you are.”

Everett frowned. “Uh-oh. I hear a but coming.”

I sighed. “I think you’re amazing. But unfortunately, I don’t think I’m ready to get back into dating after all. I realized that I’m not over the guy I was seeing. You’re a man who goes to the trouble of finding a new restaurant just to make sure you give a relationship a fresh beginning, so you deserve a person who’s ready to give you the same in return. I wish I could do that, but my head is stuck somewhere else.”

He nodded. “I get it. And I appreciate the honesty. Wells wasn’t exaggerating when he said you’re something special.”

“Thank you.”

“I’ll tell you what, if something changes, give me a call. Maybe our timing is just off.”

I kissed his cheek. “I’ll do that. Thank you for understanding.”