First Time: Penny's Story (First Time (Penny) Book 1) Read online

  Chapter One

  Get your mind set. Confidence will lead you.

  That’s what the fortune cookie that had come with my Thai lunch had said. And yes, I knew that fortune cookie fortunes weren’t supposed to be real, and also that it didn’t make any sense for one to come with Thai food. But fortune cookies aren’t really Chinese. They were just made up in America and sold with Americanized Chinese food. So, if it didn’t make any sense that they should come with Thai food, but they did, anyway, then what was to say the fortunes couldn’t be real, even if they weren’t supposed to be?

  Standing on the sidewalk outside the wide white stone arch and tall double doors of One If By Land, Two If By Sea, I tried to get my mind set. Waiting inside the restaurant—hopefully still waiting, since I was about ten minutes late—was a guy who was supposed to be “perfect” for me. Or so said my boss.

  “Trust me, he’s perfect for you.” Sophie had barely looked up from her phone as she’d texted him. She had a way of saying things that made her sound like the expert in whatever she was talking about, so I’d gone along with it.

  Then she’d paused, squinted up at me and asked, “Maybe perfect? How do you feel about older guys?”

  How did I feel about them? Sophie was married to a guy twice her age, and she seemed happy. If it was no big deal for her, why did it have to be a big deal for me?

  The problem was the guy I was meeting wasn’t just twice my age. He was thirty years older. He was a year younger than my dad, and two years older than my mom. And he was divorced. I’d never dated a divorced guy before. What was he going to expect?

  This whole situation felt way too adult for me. I was an adult, but you know. Not a real adult. I was only twenty-two. Give me a 401K option, and I was on the phone to my dad quicker than you could say, well, “401K option”. I had no idea what I wanted to do with my life, aside from the vague “I’d like to have a husband and kids someday” that Sophie had found so compatible with her half-century-old friend.

  Everything since the day I’d graduated college had been a confusing mess, and this wasn’t an exception. Was I really cut out for this?

  Plus, there was my virginity, that one teensy complication I wasn’t sure Sophie had accounted for. I had a hard enough time finding guys my age who were cool with not having sex; a guy who’d been thirty when I’d been born would probably be long past his days of patiently waiting for silly girls to sleep with him.

  I fished the scrap of fortune cookie paper from my pocket. Get your mind set. Confidence will lead you. Maybe making up my mind would give me confidence?

  I squared my shoulders, took a deep breath, and stepped toward the entrance. The doorman rolled his eyes as he held the door open. I didn’t blame him; this was my fourth attempt to come in. I lifted my chin and pretended not to notice him. Oh! There was that confidence I was supposed to be getting! The worst that could happen, I reasoned as I stepped inside, was that I would meet this guy and not like him.

  The restaurant was super dressy. Sophie had advised me of that beforehand, thank god. I’d worn my “Fête to Print” dress from ModCloth, because the subtle sequins and deep teal color made my eyes sparkle. I’d also worn about sixty pairs of Spanx to smooth everything down. I remembered my mother’s motto: Definite jiggle calls for decisive measures.

  I walked in like a person who could breathe and smiled at the maître d’ as though I knew exactly what I was doing. “I’m here to meet someone. The reservation is under…um…Pratchett?”

  “Of course. This way.”

  I followed along behind, my gaze darting nervously around the candlelit dining room. Shining silver chandeliers hung from the ceiling in front of a leaded glass rose window. Paintings of colonial figures hung on the walls, and diners sat at round tables with more candles. I was surprised it wasn’t seven hundred degrees in the room from all the fire. This was exactly the kind of restaurant I’d been forced to go to for my father’s work occasions or my mother’s social functions. That didn’t make it very easy to relax.

  As we wound through the tables, I saw a guy near the corner who looked like he could be fifty-two, but he was with a woman who looked like she could be, as well. Another man sat at a table alone and looked very pissed off. I hoped that wasn’t my date.

  “Mr. Pratchett? Your guest has arrived.”

  I nearly collided with the maître d’s back; I’d been too busy staring at the mean-looking man and corner dude. I stopped short and teetered in my matte black heels before I looked at the guy sitting at the table we’d stopped by, the guy I was actually there to meet.

  The first thing I noticed was his eyes. They were very green and looked…concerned, I suppose would be a nice word for it. Terrified would be more apt but less kind. I wondered how bad I looked that he made the expression he did. It was hard to remember to assign myself blame for his reaction when it was so easy to focus on his intense gaze.

  He stood. He was impressively tall. Sophie hadn’t mentioned that, or the fact his black hair had a very hot going-gray thing happening. She also hadn’t warned me that he had a weird, magnetic sort of charisma that would shock me to my toes.

  His smile crinkled the corners of his eyes and drew lines around his mouth. “Penelope?”

  “Penny,” I corrected him, then regretted it. This restaurant was not a place were a Penny would go. This was a place for a Penelope if ever there was one.

  “Ian.” He put his hand out. I gave him mine, afraid he might try to kiss it. I hated it when guys tried to do that. Instead, he gave me a very firm, very awkward shake.

  Okay. That was one way to start a date, I guessed. Maybe I should have brought my résumé.

  The maître d’ pulled my chair back, but Ian waved him off. “Let me. I’m trying to impress the lady.”

  That was cute. I’d give him that. He helped me scoot my chair in, and his fingers accidentally brushed my back. Tingles shot straight up my spine. So, clearly I’d gotten over my fear that I might not find him attractive.

  When he took his own seat, he didn’t say anything for a moment, and I worried that I had a tell, some twitch about me that clued him in to my thoughts. It was difficult to hold up under that scrutiny without cracking. I giggled and covered my mouth with one hand to hide it. “What are you looking at?”

  “You,” he said with an answering laugh. “You’re… Well, I wasn’t expecting you.”

  “Oh? What about me is so unexpected?” I flashed him a big smile, as though I were sure he’d say something overwhelmingly positive. Because no matter how he responded, I would just react as though it was complimentary. It was one of my ways of coping with extreme embarrassment. Just ignore whatever happened and move on. Since I found myself routinely embarrassed, I’d gotten really good at that technique.

  “Well, maybe I should have assumed, because you’re Sophie’s friend…” He sat back in his chair and cleared his throat. “But I didn’t expect you to be so young.”

  That was not even slightly what I’d thought he was going to say. “I assumed Sophie had told you that our ages were…way different. She told me.”

  “She probably figured you needed more preparation.” He reached up and brushed the side of his nose with his thumb.

  “H-how so?” I asked, my gaze following that hand down until it disappeared under the table. Oh, wow, Sophie was right, he really does have attractive hands. But more importantly, Sophie hadn’t told Ian that I was younger than him? That was so rude!

  He leaned forward slightly, as though he were telling me some huge secret. “Imagine if you came in here, expecting some young, handsome guy, and here was
a slightly fat, gray-haired old man. The fact that you showed up at all is reassuring.”

  “Wait a minute, are you comparing me to a young, handsome guy? That’s kind of a weird compliment, but I’ll take it.” Usually, I hated when people made self-deprecating comments. It was hard to form a response to them, and it made me uncomfortable. Of course, a year ago I’d been making them nonstop; Sophie and Deja’s confidence had rubbed off on me.

  But when Ian described himself so candidly, it made him seem genuine. Like he didn’t care if his flaws were on display, and it didn’t matter who brought them up first.

  “When you put it that way, it does sound like a strange way of flattering you.” His smile was a bit goofy and lopsided. Boyish, even, though I wasn’t sure if that was supposed to be a good thing.

  I liked it, anyway.

  “But you are not fat,” I corrected him seriously.

  He made a face. “You haven’t seen what’s under here.” He gestured to his chest with an open palm, as if to encompass the whole of his body. “This is all a gory wreck, courtesy of the ravages of age.”

  “Oh, shut up.” My laugh startled me with the revelation that I had actually relaxed some.

  A waiter came over and offered us a wine list. Why do they always show up right when things are getting interesting? I listened to the man as he rattled off a lot of words I didn’t understand. To my horror, Ian was looking expectantly to me.

  “Oh, um. You pick?” I looked from the waiter to Ian, my nails digging into my palms before I realized I was clenching my fists below the table. It wasn’t as though I’d never been to a restaurant that had a wine list. I was just used to my parents ordering without consulting me.

  “We probably don’t want to order the wine until we’ve decided what we want from the menu. These are just suggestions to keep in mind,” Ian said, and I instantly knew I’d made a gaffe. The waiter had probably been pointing out something of interest, not asking for our choices. Still, Ian played it off like it was no big deal and took the list. When the waiter walked away, Ian said, “Pardon my curious expression, I was just trying to figure out if you were of legal drinking age.”

  He winked at me, and my stomach took me by surprise with a giddy flutter. I felt the color rising in my cheeks. “Yes. I’m old enough. I’m twenty-two.”

  He made a low whistle. “That is…young.”

  Back to the crux of the issue. Why did I get the feeling that if Sophie had told him, he would have turned down the date? Which was all the more reason for her to have been honest. Now I was here, feeling foolish and unwanted, going through the motions of a date with someone who’d changed his mind.

  I plucked up my courage and said, “Look, I’ll understand if you’re not cool with the age gap. I’m not going to be offended.”

  “Oh, neither will I, if you decide it’s mad to be on a date with a man who’s old enough to be your father,” he assured me, still with that oddly endearing bluntness about himself. “But I came to meet a woman with whom my friend thought I would ‘work wellʼ. I think it would be short-sighted of me to not at least get to know a little about you.”

  “And I…” …know that you’re staying here because you feel bad, and everything is going to get a thousand times more awkward. But he was right. Sophie had matched us up for a reason. It would be silly not to at least try to find out why. So I finished, “…would like to get to know you, too.”

  “Excellent.” He paused. “Although, at the moment, I’d like to get to know the menu. They brought them while I was waiting. I think they were hinting I should do something or surrender the table.”

  I winced. “Sorry I was late.”

  He waved a hand. “No, no, don’t worry about it. It’s New York, for Christ’s sake; everybody’s late going somewhere.” He looked back down at the menu.

  Back in olden times, the dude picked up the check at dinner. But this wasn’t olden times, and I liked to buy my own food. This place, though, was just slightly out of the price range I was comfortable with. I liked fancy food, but I also liked paying my rent.

  The lines of print wobbled in front of my eyes, and I looked up to find Ian tapping my menu. Shit. He knows I’m broke.

  Somehow, when it came to money, I always felt stupid. Maybe because my parents had drilled into my head, every moment since birth, that I should “behave rich, live cheap”. Having someone be able to tell you can’t afford something? Just by looking at you? Horrifying.

  “I hate to sound old fashioned,” he began, and the crushing discomfort of the moment increased ten-fold, “but when it comes to some things, I am. Since I picked this restaurant, dinner is on me.”

  “Well, thanks.”

  He tapped the top of my menu. “Just so you know, that’s not me angling for sex.”

  “I didn’t think it w-was,” I stuttered. Oh god, get that under control. The embarrassment train had derailed and spilled toxic embarrassment waste all over the place. I tried to make a joke of it, saying, “That was mortifying,” but it didn’t land.

  I wasn’t just embarrassed. I had second-hand embarrassment for myself.

  Worst of all, he seemed to take my remark personally. “I know, I’m sorry. I heard it as it was coming out, and I couldn’t stop it.” He paused and muttered, “damn,” under his breath. “I haven’t done this in a long, long time, and I just didn’t want you to get the wrong impression. I tried to look all of this up on the internet and—”

  “You researched how to date on the internet?” I interrupted. That was so adorably vulnerable. Under all the weirdness and self-deprecating humor, he seemed like he was probably a very confident guy. I guess you’d have to be, to try and re-enter the dating pool with a complete stranger. I almost suggested he try this over, but with someone he knew well. Then I found myself becoming a little defensive and prickly over his imaginary next date, like she was moving in on my turf.

  So…that was strange.

  He winced slightly at my question. “I did. I’m not sure how great the advice was…”

  “Tell me some of it. I can coach you,” I offered. I put my menu down—I think I’d decided on what I wanted, anyway—and leaned my folded arms on the table. And, what the hell, I’d try to flirt a little. “I’m excellent at dating. I do it all the time. Sometimes even twice with the same guy.”

  Oh. My god. Who the frick am I, Mae West?

  “Then, you sound like quite the expert.” He was still deciding on food, so I couldn’t tell what he was thinking. I hoped he didn’t think I meant I was going on another date later and wasn’t invested in this one. He set the menu aside, sat up straight, and said, “All right. Well, the first suggestion was ‘don’t talk about your exes’.”

  “That’s definitely good advice. Don’t talk about that until… Well, I don’t know when. But I don’t want to hear about it,” I blurted. How are you still doing this? I was never this disoriented around a guy. I like guys. And I know I’m cute and fun to be with. I’ve had enough men tell me that. But my game had totally deserted me the second I’d gotten out of the cab.

  “Oh my god, that sounded so rude. I’m so sorry,” I apologized. Sophie had even told me he was newly divorced. I’d probably opened up some awful wound.

  He started to wave it off, saying, “Don’t worry about—” but our waiter came to the table, and he seemed a little impatient.

  “Have you made your selections, then?”

  Rude. I thought they were supposed to be nicer in fancy places like this.

  Ian gestured to me. “If the lady is ready.”

  I’d totally forgotten what I’d wanted. I’d been concentrating on how much I was messing up this date. He was staring at me, probably wondering why I couldn’t function like a human being, so I stalled, saying, “Oh, you go first.”

  “Sir?” the waiter addressed him.

  “I’ll have the warm octopus eschabeshe, I think.”

  Of all the characteristics that define me as a person, the one that I truly be
lieve will be mentioned not only in my obituary, but my eulogy and the engraving on my headstone is my unwavering passion for octopods. They’re one of the most intelligent, if not the most intelligent, invertebrate. They can solve puzzles and navigate mazes. They’re incredible escape artists. Of all the creatures in the sea, they are by far my favorite. Actually, of all the creatures on the planet. I’d take a pet octopus over a pet dog, any day.

  So, when this previously charming stranger announced his intention to eat one, every instinct I had was to flip the table and shout, “No!” at him like he was a puppy who’d gotten into the trash.

  Instead, I made a high-pitched noise that was completely out of my control.

  He raised an eyebrow and leaned slightly forward. “Is there something wrong?”

  “No, it’s nothing.” The smile on my face felt like when you’re waiting forever for someone to take a picture. “I just really, um. I really like octopods.”

  In a split second decision, I made up my mind to walk out of the restaurant if he tried to correct me with “octopi”.

  Instead, he looked a little impressed and said, “Really?”

  “I do this donation thing to conserve the habitat of the giant Pacific octopus. Enteroctopus dofleini?” I glanced up at the waiter, whose expression said, quite clearly, please stop talking. But I couldn’t. Conversational self-preservation is not a skill I possess. “But I love all of them. I even have a tattoo of one.”

  For a long moment, Ian just stared at me. Probably because he thought I was demented or that I had a little bucket of red paint in my purse to throw over his dinner, right before I ripped my dress in half to reveal a PeTA T-shirt underneath. That might have been why he said, “Then, I revise my selection, and I will have the lobster pappardelle, instead.”

  “And for you, ma’am?”

  I wasn’t sure if I should eat dinner since I’d already filled up on butterflies. My hand shook as I gave the waiter my menu. “The frog legs, please.”

  “Very good. Do we have a wine selection?”

  A smile flickered at the edges of Ian’s mouth. “What goes with frog legs?”