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

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

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

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

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

This whole situation felt
way too adult for me. I was an adult, but you know. Not a
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

I fished the scrap of
fortune cookie paper from my pocket.
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

Of course. This

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

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

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

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

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

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
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

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

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

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

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
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

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

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

And I…”
…know that you’re staying here because you feel bad, and
everything is going to get a thousand times more
. 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,

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
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.

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