Second First Dates

by Gabriella Gamez

Genres: Women's Fiction; Contemporary Romance; Romantic Comedy

Synopsis

A librarian swipes right on a charming high school teacher, only to realize that she’d already dated him once—and it ended in disaster.

Leti Maldonado has heard all the dating horror stories, but she never expected to be part of one after coming out of a four-year dating hiatus. When she matches with Julian Gutierrez, she doesn’t think much of how familiar his profile picture looks. But when the date goes awry, it unlocks the terrible first date memory that made her quit dating in the first place—because she’s been on this date before. And it’s just as bad the second time around.  

To make matters worse, at the end of the night she discovers Julian lives in the same apartment building as her and his roommate is her younger brother. From then on, he’s inescapable. In the mailroom. In the stairwell. Outside her door with a takeout mix-up. He’s even a witness to yet another of Leti’s terrible first dates.

When Julian suggests taking over her dating accounts, he makes a surprisingly convincing case. If Leti’s proved anything, it’s that she sure doesn’t know how to pick ‘em. How much worse can Julian be at picking dates for her? It’s a terrible idea, but at this point he might be her only hope of finding real, lasting love. If they don’t fall for each other in the process, that is…

Release date: July 28, 2026

Publisher: Grand Central Publishing

Print pages: 384

Sample

For the first time in four years, I’m officially dating again.

My phone pings after my last swipe, alerting me of a match. As Julian Gutierrez’s boyish grin lights up my screen, I can’t help but return his smile. Never mind that there’s no one around to see me cheesing in my bedroom on a random Tuesday night, but I digress.

He has tan skin, dark hair, and if his profile is anything to go by, a personality on par with his aesthetic attractiveness. The smile in his first photo, which captivated me from the get-go, extends to kind, sparkling brown eyes that would surely melt me to the floor if I saw them in person. On top of that, his hair is a bit long in that wavy, slightly messy way that’s always been my type when it comes to men. He’s wearing black-framed glasses in his third photo, which nearly did me in.

As I read more about him—high school American history teacher, demisexual, enjoys long romantic walks, witty banter, and a good rom-com in book or movie form—the more intrigued I am to get to know this guy. I’d barely finished going through his profile before swiping right and was immediately notified that we’re a match.

Despite my excitement, there’s something familiar about Julian that’s nagging me, but I can’t place where I could possibly know him from. It’s times like these when I wish regular people had an IMDb profile I could look up at any given time and go, Oh, yeah, you were the boy who sat behind me in sociology class six years ago—that’s where I know you from! Not that I took a sociology class in college, but still.

My phone pings with a message from him, and another smile can’t help but inch its way across my face.

Julian: Leticia Maldonado, as I live and breathe.

I furrow my brows as I read the message. Is this his idea of a pickup line, or have I met him before? He sends a follow-up before I can overthink it.

Julian: So you’re into Stardew Valley, huh? Which NPC did you marry?

Leti: Do you play? As a streamer, I’ve married all of them at one point or another, but Harvey’s always been my favorite.

Julian: Just started on PC and I have no idea what I’m doing

Julian: So, Harvey, huh? I feel like I have a pretty strong resemblance to the guy. Are you telling me you have a type?

Leti: Now that you mention it, aside from your lack of a mustache, I can see it.

Julian: Say the word, and I’ll grow one. I can’t promise great results, but at the very least that’s where stick-ons come in handy.

I can’t help it. I let out an honest to god giggle. It’s enough that I barely recognize myself. I live in snark like it’s a second skin. I don’t giggle at things cute strangers say to me through DMs. I shouldn’t already be this happy about flirting with a stranger online, especially since the last time I got involved with someone behind a screen she ended up falling for someone else.

Which is why I’m not making the same mistake again. As soon as I find the right moment, I’m going to ask Julian on an in-person date. Better to know right away if we’re compatible rather than waste months on a text relationship going nowhere.

Leti: No need. You’re pretty cute already, the stick-ons might give you a complex.

Julian: I appreciate you for noticing how cute I am.

Julian: I nearly choked on my coffee when I swiped to your third picture, btw. I knew you were beautiful, but damn, you in that baby blue dress nearly stopped me from breathing.

He’s referring to a picture my best friend, Bella, took of me last month. I’d bought the dress a few years ago when it was on mega-sale and two sizes too big, and now the thing fits me like a glove. Three and a half mimosas into brunch and feeling myself, Bella had me pose in front of a bush near our table with these pretty, white blooming flowers. “Get my good side,” I remember telling her, holding up my drink as I kicked a leg up Princess Diaries style and turned my head over my right shoulder to smile at her phone lens.

There’s a sort of “come hither” vibe to my sly smile, but the round apples of my cheeks soften the look so I’m more innocent than sexy. Coupled with the dress that rides up my thigh and highlights every curve on my body, I sort of feel bad for the guy—which is not a feeling I’m used to.

Back in college, I would’ve hated how the photo turned out. It used to be so easy to pick myself apart: My cheeks are too round, the dress is too tight around my middle, everyone can see the cellulite on my thighs. At some point, I got older and started saying “fuck that” to the voice in my head and allowed myself to believe when people tell me I’m beautiful. Who am I to question their entirely correct opinion? Maybe that’s why I’m not at all surprised by Julian’s reaction, though I am pleased by it.

Julian: Actually, I did stop breathing for a moment there. I choked on my oatmeal and my roommate almost had to do the Heimlich maneuver on me.

Leti: You poor thing.

Julian: Cruel woman. Does my pain mean nothing to you?

Leti: There, there.

Leti: I can’t imagine how you would’ve explained that to the paramedics.

Julian: Easy. They’d understand perfectly after I showed them your picture.

Julian: Wow, I can’t believe how easy this is.

Leti: How easy what is?

Julian: Talking to you. Last time didn’t work out so well for me…

I assume he means the last time he matched with someone. To be honest, I’m a little surprised talking to him is so easy too.

Leti: I get it, believe me. I haven’t dated in a few years so I thought this would be much harder.

Three dots appear and disappear for a few minutes as he types his reply, ratcheting up my anxiety. Then they disappear entirely. Guess I spoke too soon. I bite my nail for a moment, thinking. Was I too honest? Is he unsure of how to respond? Maybe we need more harmless small talk before we start divulging our dating histories.

Leti: So, rom-coms, huh? Do you have any favorites I should know about?

His reply is immediate, and I breathe a sigh of relief.

Julian: Too many to name. I don’t want to overwhelm you.

Leti: I understand, it’s like asking me to pick a favorite video game. The answer changes every week.

Julian: Exactly!

Leti: We should see a rom-com together. Dinner and a movie is the perfect first date, right?

Minutes go by without a reply, and doubt starts to creep in again. It’s not exactly the smoothest transition, but I can’t risk liking him any more than I do without a clear indication that this is going somewhere. Hence, the blunt ask-out.

Leti: I really like talking to you, and I think we’d have a lot of fun together. How does next Saturday sound?

An entire hour passes without a response, effectively bursting my bubble. I guess what they say is true—if he seems too good to be true, he probably is.

There’s a strange pressure that comes with being the last single sibling.

Elena found the love of her life so easily. One glance at Diego sitting two rows down from her in their college auditorium and my older sister was a goner. They did everything the “right” way, according to my parents. They met young, fell in love, walked the graduation stage together, moved into a new apartment, got married a year later, and then started a family. Now they live in a house larger than the one we grew up in with an actual, honest-to-god white picket fence. It’s nauseating.

At least my younger brother isn’t moving in with Kayla yet. After finishing undergrad, Andrew has officially moved out of student housing and into his first adult apartment, though he’s still living with a roommate. I don’t know why it had to be the same complex as mine, something I’ve asked numerous times before and after he signed the lease. I can count on one hand the number of conversations we’ve had that haven’t devolved into shouting matches. Maybe there was a time after high school I thought that might change, but some cuts run too deep to ever fully heal. Which is why, up until now, my method for dealing with Andrew has been to not deal with him. It’s easier on both of us that way.

At least, it was until we became neighbors.

Since I conveniently missed his moving day (like the bad sister I am, I said I was sick and spent the whole day playing video games), I have to scroll through the family group chat for his apartment number. He lives one floor down from me. If I had my way, I wouldn’t have let Elena guilt me into this admittedly overdue visit, but I’m at least comforted by the fact that I won’t have to be alone with Andrew.

At the sound of my name, I whip around toward an open door and my brother waves me inside.

“Look who finally decided to come down for a visit.” Andrew shakes his head as I step past him. This is bonkers. His apartment is practically right underneath mine. “Elena and Diego are already here.”

“They got a pass on moving day. Why don’t I deserve one?”

“They have two kids.”

“And I was sick.” I roll my eyes before inspecting the place. It’s the exact floor plan as mine, only inverted and with sliding doors that lead to a spacious patio area complete with its own barbecue pit. Meanwhile, all I have is a small square balcony with a view of the strip mall across the street.

The pitter-patter of my niece’s and nephew’s feet echoing from the hallway makes me realize Andrew’s not very far from that life himself. If I blink, I can almost imagine this is the apartment he shares with Kayla, and the pitter-patter is coming from his own little one running around, wreaking havoc. And then I’ll not only be the last single sibling, but also the last one to have kids. However, as much as I love being an aunt, I’m not sure I want kids of my own.

“Speaking of kids…” He crouches, making scary monster noises as he darts off toward the sound of footsteps, and that completes the picture in my head.

He’d make a great father someday. It’s not that I’m jealous of the lives my siblings have created for themselves, exactly. It’s just that they figured out their lives so quickly, and I’m still catching up. If I’m the one thwarting convention, why do I still feel so inferior?

“No running in dark corners!” He emerges from the hallway carrying Alicia in his arms. “I almost ran you down like a bowling pin.” He strokes her hair back affectionately. She burrows her dark, curly head into the crook of his neck, content. Andrew glances up at me suddenly, and I realize I’m staring. “What?”

“I swear to god, if you and Kayla have kids before I have my first real relationship—”

“Whoa, slow down.” He lets out a nervous laugh. “Kayla and I haven’t been together long enough to be talking about…all of that.”

I stare at him for a beat. “You’ve been together for almost a year.”

“Exactly. I’m gonna need about four or five more before I decide to end my life before it starts.”

Before I can roll my eyes at such a classic Andrew response to even the thought of settling down, the clatter of tinier feet sound from behind, where Diego is carefully following behind his eight-month-old. Mateo only started walking a few weeks ago, but once he started there was no stopping him.

“Come here!” I scoot forward on the edge of the couch, slapping my knees until Mateo looks up at me with his big, brown eyes. “Come here, Mateo!”

“He’s not a dog.” I ignore my brother and keep my focus on Mateo. At the sound of his name, he rushes forward. Once he’s close enough, I sweep him up off the ground and into my arms. He giggles into my shoulder as I coo baby nonsense at him.

“So, why are you upset?” Diego asks, having only caught the last half of our conversation.

Before I have the chance to answer, Andrew chimes in. “Dating prospects don’t look so good.”

I glower at him, covering Mateo’s eyes from my death stare. He’s too young to witness such a look from me.

“There’s something I don’t miss.” Diego chuckles. “The chasing, the games. Elena and I lucked out meeting early in life.”

“My prospects are fine, thank you very much,” I lie, thinking of the last message I sent to Julian and kicking myself for jumping the gun. Right when I thought I’d lucked out, I had to go and scare him away. Actually, fuck that. If he scares that easy, I’d rather wait to meet someone better. I’m through changing myself to be more palatable to a romantic partner. I learned my lesson a long time ago.

“I thought being bisexual was supposed to give you twice the options,” my brother says. “It’s been, what, ten years since you’ve been in any kind of relationship? You’re too far gone to try dating apps now. At this point, just head straight for a convent.”

He snickers at his own joke, and Diego merely shrugs and sends me an apologetic look. I wave it off, unfortunately used to my brother’s twisted sense of humor by now.

“Biromantic,” I correct, more to myself because this is far from the first time I’ve had to. “And it’s only been four years, not that it’s any of your business.”

Are we conditioned as a society to immediately forget and dismiss what we don’t understand, or is that just my brother? Every time I try to explain that I’m ace-spec, he covers his ears and says he doesn’t need to hear about his sister’s sex life. Not that I’ve ever had one, but I’m not about to let on that his convent comment is too spot on for my liking.

Despite Andrew and I being closer in age, Elena is the sibling I’m closest to. Growing up, she could always tell when something was wrong with scary, maternal-like accuracy. When I got my period for the first time, I ran to her for answers instead of our mother. When none of my high school crushes worked out, I sought her out for comfort. When I realized I didn’t experience sexual attraction like everyone else—that I didn’t really understand what it was to begin with—she pulled up the asexual visibility and education network website on her computer and showed it to me.

“Tell her she needs to get off the dating apps!” Elena calls from the hallway, and I roll my eyes when Andrew breaks into another fit of laughter.

“What is she doing back there?” I ask Diego.

“Babyproofing before we leave the kids for the weekend,” he says. “I finally convinced her it’s time we take that vacation we’ve been talking about for years.”

Andrew grumbles to himself, and then calls to Elena, “You better undo everything you’re doing over there when you get back!”

“I still don’t understand why she won’t leave them with me.” Mateo makes a gurgling noise, which I take as commiseration. “See, Mateo agrees. He’d much rather stay with me.”

“Don’t you start.” Andrew glowers at me. “Elena never lets me babysit, and you’re half the reason.”

“What are you talking about?”

“You convinced her I’m not responsible enough to take care of my own niece and nephew,” he says. “I had to get Diego on my side before she agreed to let them stay here.”

“Leave me out of this.” Diego holds out his hands in surrender.

“I never told her you’re not responsible.” I turn my nose up at him. “I’m practically a co-parent by default, living with Bella and her daughter. Between you and me, I’m the most natural choice to babysit. If she thinks you’re irresponsible, she came to that conclusion all by herself.”

“Yeah, right,” he says gruffly. “I can handle babysitting.”

“For an afternoon, sure. But a whole weekend?” I glance at Diego. “Are you sure this is a good—”

He shushes me before the whole question is out of my mouth. “Not so loud,” he whispers. “She’s still looking for any reason to cancel the trip.”

I’m cut off from replying by the sound of my sister’s footsteps, followed by her voice.

“Don’t be afraid to go out and meet people in person.” Elena steps into the living room, holding two hot-pink baby gates under her arm. She starts setting up the first at the hallway entrance, continuing, “I can’t imagine how anyone meets someone who wants a serious relationship on those sites. It’s one big machine contributing to hookup culture, which we all know is the last thing you want.”

“So what would you have me do?” I hand Mateo off to his father before rising from the couch, ignoring Andrew’s sputtering. “Walk up to the first cute, age-appropriate person at the grocery store and strike up a conversation?”

“Why not?” Oh, how naive my married, mother-of-two sister is.

“Wait, hold on—” Andrew shoves past me to reach Elena. He shakes the gate while Elena is still putting in the screws and her face twists in annoyance. “How do these things even work? I have a roommate, you know.”

“And I sincerely hope he’s good with kids,” she says to him, pointing an accusing finger at his chest. “I would’ve liked to meet him before leaving my children here, you know. I’m nervous enough as it is leaving them with you.”

“They’ll be fine.” He waves her off, which would be bad enough on its own if he hadn’t added “He won’t even know they’re here.”

Elena looks past him to her husband, a knowing expression crossing her face as his turns pleading. I’ve seen them have enough silent conversations with their eyes to know what’s coming. When she looks back at Andrew, she throws her hands up in the air. “That’s it. I can’t do this.”

“Wait, Elena!” Diego rises from the couch to follow as she storms back into our brother’s room.

“Good going, Andrew.” I shake my head at his confused expression.

“What did I say?”

“The exact thing she needed to hear to call off their first vacation in five years.”

His eyes widen in alarm before he turns around. “Elena, wait!” He follows after them to his bedroom. I want no part of this, so I return to the couch where Alicia is taking a nap. I pat her head while I take out my phone to check my notifications. I’m not sure if I’m more shocked or annoyed to see Julian’s name on my lock screen.

Julian: So sorry about the late reply, it’s been chaos getting everything ready for my first year teaching. I’m practically living in my classroom right now.

Julian: I’d love to go out with you. If you’re still interested, that is.

Leti: You leave me hanging for two days after I put myself out there, and NOW you want to go out? Pretty sure your school has enough wi-fi to manage a simple yes or no reply, even if you are living there.

Julian: You’re right. It was a lame excuse, and I’m sorry.

Julian: The truth is…you surprised me.

Leti: In a bad way?

Julian: No. I didn’t expect to like you so much, and I got scared I wouldn’t live up to your expectations if we met in person.

Leti: That’s fair. If it helps, I’m a little scared I won’t live up to yours either.

Julian: Not possible.

As my siblings fight in the next room, I find a smile inching its way across my face. On any other day, it’d be me fighting with Andrew in the next room while my sister and her husband make googly eyes at each other on the very couch I’m sitting on. What upside-down world am I living in?

Leti: Fine. Next Saturday is on.

When next Saturday rolls around, I’m anxious the whole day until it’s time to start getting ready. It’s a no-brainer to wear the blue dress that nearly made him choke, given that he’s already expressed how much he loves it. I inspect my outfit in a full-length mirror, turning every which way to get a glimpse of myself from all angles. The dress is cinched at the waist and stops a few inches above my knees, and the color makes my tan skin glow. My black hair is tied in a loose French braid that falls over one shoulder, a few short tendrils loose to frame my face.

As I’m finishing my makeup, it hits me that this is the first time I’ve gone out with someone since college. I’ve gone four whole years without romantic prospects of any kind, with one very brief online exception. I knew better than to get my hopes up after sliding into a TikTok influencer’s DMs, even if she did live in town. But I thought we’d had a connection, at least until it turned out Angela Gutierrez had a stronger one with someone else.

If that experience taught me anything, it’s that strictly message-based communication is not for me. I’m a grown adult, dammit, and I am going to date. Perhaps I’ll have better luck with Julian Gutierrez, despite them having the same last name. Maybe that’s why he looked so familiar to me. He and the woman I almost dated could be related. I’ll have to ask him about it tonight.

Julian picked the restaurant after asking what I was in the mood for. Sapporo is one of my favorite sushi restaurants in town, which is an excellent sign for the night. I’m the first to arrive, so I take a seat on a bench outside the restaurant to wait for him. We agreed on 7:30, but it’s already ten after. And to think, I thought I was pushing it when I broke out the flat iron for my hair framing pieces. A fruitless pursuit, since sitting out in the humidity for two seconds has already frizzed up my hair.

He doesn’t show until eight, not that I’ve been constantly checking the time or anything. I recognize him immediately as he heads to the building from the parking lot. I wish I could say I’m too annoyed to notice how good he looks, but that would be a lie. There’s a light flush on his cheeks as he pushes the brown curls from his eyes and crosses the lot in a rush. He’s dressed casually in jeans and a button-down, the sleeves rolled up to his elbows. When he smiles, he’s the spitting image of his profile picture—lines crinkled at the corners, deep dimples burrowing both cheeks.

“Leticia.” I don’t hear the sound of his voice over the chatter of people, but I watch his lips as they mouth my name. Normally I’d be weirded out by someone calling me by my full name, but a strange sort of heat warms my stomach instead. I’ve so rarely experienced sexual attraction before, and it couldn’t have come at a more inconvenient time. I should be angry he left me waiting—a second time, at that. Not thirsting for him after watching his full lips move around the shape of my name.

Besides, there’s a note in my dating profile to call me Leti. I should be annoyed he’s decided to ignore it. With those final butterflies stamped down, I wave a hand in greeting when he’s standing in front of me. That strike of familiarity intensifies as he wraps an arm around my shoulders in a side hug, and a strange sense of déjà vu washes over me. “I’m so sorry I’m late. I feel terrible for keeping you waiting. I got caught up getting my classroom ready, and then there was an accident on the way over.”

“It’s Leti, actually. And no problem.” I shrug, hiding my annoyance—for now. Even in the shade, I’m sweating bullets. The back of my dress is sticking to my skin, and I make a concerted effort to keep my arms down in case I have pit stains. “But we should probably check in soon. It’s starting to get crowded.” We’ll be lucky to get a table within a thirty-minute time frame. I could’ve checked in earlier before the dinner crowd showed up, but I would’ve felt bad taking up a table for twenty minutes waiting for Julian to arrive.

“Forty minutes?” I nearly shout after checking in with the hostess, managing at the last moment to keep my voice even. There’s no way we’re making the movie after this.

“We could go somewhere else…” Julian suggests, looking unsure. “But other places might be just as bad. Leti, I’m so sorry—”

“It’s fine.” I nod at the hostess, who says she’ll call my name when a table becomes available. With that, we head back outside to wait. “Your classroom better look like the freaking Sistine Chapel.”

I’m not sure how I expect Julian to react to my crabby comment, but the laugh that bursts out of him surprises me.

“That may be expecting a lot from my tiny portable, but it’s coming together,” he says, smiling brightly. “I couldn’t resist coming in on a weekend. I’m stoked for my first year.”

“You’ve got that new teacher excitement on your face,” I tell him, trying and failing not to be charmed by this man. “I hope you don’t lose that. I’ve seen burnout happen to too many first-years.” I let out a tired sigh. “We had two teachers quit three months into the school year last fall. I’ve been filling in for them so much, I forgot what the inside of the library looks like.”

“I had a blast student teaching in the spring. And it took an extra two years to complete my degree while working at the same time, so if it doesn’t pan out, it would seem like a waste,” he says. “But I take it you’re not a fan of subbing?”

“It’s the worst. I’m nothing but a glorified babysitter, and these kids get more horrific every year. I can’t believe you willingly signed up for this.”

“I like working with kids.” He shrugs. “I can handle a little horrific. It’s part of the job. Isn’t it part of yours, too, as a school librarian?”

“In much smaller, more manageable doses, sure. But for the amount of subbing I’ve had to do, I’m overdue for a crash course in classroom management.”

“Yeah?” He leans in. “I can help with that. What’s giving you trouble?”

“You mean besides the constant talking over me, copious cases of plagiarism, and the spitball ceiling?”

“For the first, the trick is to stare them down until they stop talking. I learned that one from my mentor teacher. And we have software that catches most cases of plagiarism. As for the spitball ceiling, I’m at a loss.”

“Guess that means you can’t help with the drug situation either.”

“I’m sorry—what?” He rears back. “Please tell me you’re at a high school. Not that it’s much better than sixth graders doing drugs, but still.”

“It’s high school,” I say. “There’s this portable bathroom on campus that they go to smoke in, and it’s not nicotine in their vape pens.” I have to laugh because the truth is too depressing. I’ve written up at least three kids on a normal day of subbing. “What’s your solution to that?”

He’s off the hook from answering when the hostess calls my name. We’re led to a table by the window and given menus as we take seats across from each other. The cool air is a relief on my overheated skin. Since we haven’t been given napkins yet, I resort to wiping the sweat from my brow with the back of my arm. Meanwhile, there isn’t a trace of sweat on Julian’s skin. Talk about unfair.

“You look great, by the way.”

“Is that some sort of joke?” I let out a sound that’s half scoff, half disbelieving laugh. “I look like a melting tomato.”

“I’m guessing you spent most of your summers indoors.”

“You’d gue. . .