Dating the Billionaire: A Standalone Romantic Comedy Page 4

  I feel like she’d whisper something about Chaucer and not know what to do with herself. The Wife of Bath, guys. She was super raunchy. Very applicable to this situation.

  I’m back at the library, because my uncanny instincts were correct: Amy got dolled up, flirted a little with Dan, and lo and behold they have a date set for tonight. The new, trendy gastropub in the East Village. All the organic bangers and mash and microbrewed beer your little hipster heart can stomach. Amy’s flitting back and forth between floating on air and plummeting to existential dread.

  “What if this is where he realizes there’s nothing cute about me? What if how much of a failure I am becomes apparent? What if I’m doomed to spend the rest of my life with a cat?”

  “Get a dog.” Christ, that came out of my mouth wrong! “I mean, dogs are better for companionship, and you’ll want one. A dog. For that Brooklyn townhouse with the cute little yard you’re going to get when you marry Dan and have wonderful babies together.” Positivity rules! Stay positive for your client! I had wild, screaming sex on the first not-date! What is happening to me?

  “I like corgis.” Amy brightens at this topic of conversation. Right. Bullet dodged.

  “And they’ll love you. So. The first date.” I show her my black leather planner, with neat bullet points in my perfect, looping cursive. I always took pride in my handwriting. Especially after I stopped dotting the ‘i’s with little hearts. “Remember, Dan pays. If he doesn’t, that’s a huge red flag.”

  “What if he doesn’t pay, but only because he thinks it’s insultingly chauvinistic to do so? Should I tell him that’s what I want?” She blinks and adjusts her glasses. “Is paying for things chauvinistic? Tumblr says yes, but Reddit says no.”

  Oh God, she’s been on the internet. Worst possible idea. No one knows what they’re doing, but they sure love talking about it.

  “If he’s the right guy for you, he should just know.” He should just know how to make you come harder than you ever have in your life why is my brain doing this?

  “Isn’t that asking him to become a mind reader?”

  Wouldn’t that be the way to go? I mean, then he’s got all your sexual fantasies, your fetishes, your social security number, your credit cards…

  When I have time away from my crazed inner monologue, I might look into writing a romantic espionage series about telepaths. I think it’d go down well.

  “You’re just asking him to be a responsible, caring man. One who is also super attractive, and has clearly had practice. A little too much practice.” My mind begins to drift again. No man can be that mind-blowingly good at sex without knowing entirely too many women. If you’ll check rule 47, it clearly states that any man who’s had more than ten sexual partners is someone to be careful around. I even included an equation: if the man’s sexual conquests number more than one third of his age, you’ve got a man whore on your hands. And who wants that? Who wants someone who knows every pleasurable place on a woman’s body? “Who wants that?” I all but grip Amy by the shoulders and shake her.

  “So…what should I do on the date again?” she squeaks.

  God, I’m letting this neuroticism bleed over into my everyday life. Stomach lurching, I remind myself that this was how it always got started when I was a kid: the spontaneity, the wandering thoughts, the uncontrollable ideas. That was a scary place to be, and I don’t want to go back. I pass her my new sheet of paper. It’s got three more (blessed, wonderful) rules on it, now that she has the Golden Four.

  Rule 18: If he’s more than five minutes late, he’s a jerk, but if he’s more than ten minutes early, he’s too nervous and can’t plan well.

  Rule 20: Talk about him more than you talk about yourself. This will hook him into being more interested in you later on.

  Rule 31: Spanx.

  Rule 49: You choose the restaurant, but let him order for you on the first date.

  “What if I have a food allergy to something he picks?” She scrunches her nose. Maybe she doesn’t like the spanx suggestion. It’s nothing personal, I throw that at every woman. It’s important.

  “Be honest about that. Honesty’s important.” Romance is all about honesty, so long as you conform yourself to a bunch of guidelines and never ever sleep with someone on the first date, because then you feel all strung out later on.

  Sometimes I wonder how good my advice actually is. Amy’s biting her lip and fidgeting with her wooden bead bracelet. Wooden beads. She brought out the big fidgeting guns.

  “Can’t we sit and talk and relax and get to know one another?” Her face flushes. “I don’t want to be someone I’m not.”

  That tugs at my heart. Amy shouldn’t have to feel she’s got to be someone new to find love…but she’s got to be prepared for anything, and the only way to prepare is to, you guessed it, follow the rules. Though maybe she doesn’t need all of them. Quickly, I cross spanx off the list.

  “Look, you took my advice before, right? He asked you out, didn’t he?”

  Amy looks up at me, owlish behind her glasses. “I suppose I felt like a good version of myself then. Now, these make me feel like I have to be someone entirely different. How can Dan like me if he doesn’t know the real me?”

  Good question. How can Dan like any of us when I sleep with a billionaire?

  What am I saying? With a sigh, I take the paper back, fold it up, and slip it into my purse. “Tell you what. Try to stay in the guidelines tonight, but play it by ear. Afterwards, we’ll see how you feel and discuss how to move forward.”

  Amy visibly relaxes, even smiles. “Okay. I can do that.”

  Again, my heart contracts. All I want is for lonely people to find happiness. It pays the bills, sure, but wasn’t the whole point of this business to create successful, lasting love? For other people? Not myself? Not with Jack Carraway, whoever heard of anything that absurd, why am I getting aroused next to the non-fiction section right now? This is all disastrously wrong.

  “One piece of advice? Try a new hairstyle. It’s a visual cue for men. It says you put extra effort into your appearance, just for them.”

  She nods. “That makes sense.”

  I ask her to text me after the date, then scuttle out of the library and into a fresh, early summer day in New York. By that I mean a wave of hot dog steam and car exhaust fumes and humidity that wallops me as I step outside. Sweat instantly crawls down my back. Right. Only one thing to do in times like this. Hit my favorite Italian bakery and have a glass of moscato while I’m at it.

  I swing into the perfect shop in Little Italy, my shoes clacking on the black and white tiles and the scent of baking bread and crystallizing sugar engulfing me. Mr. Damico, the owner, gives me a wave and a smile as I sit at a table by the window. No need to order, they know what I like here. A slice of princess cake as big as my head, tucked under green marzipan with some sugar dusted on top, a glass of moscato, and at least five minutes of Mrs. Damico telling me I’m too skinny. I love coming down here because it feels like hanging out with my Dad’s side of the family for an hour or two. While I love them, sometimes a little goes a long way.

  And yes, I know princess cake is a Swedish thing, but Mrs. Damico used to be Ms. Blomquist. New York’s a fabulous melting pot.

  While they lay out the white paper lace doilies and slide me my wine, I feel my phone buzzing in my purse. Ah, Mom and Dad, FaceTiming me right on time. I pick up with a smile, and Dad’s face pops onto my phone’s screen. He’s holding the camera too close and at the wrong angle, as usual, so I’m getting an in depth look at his forest of nose hair. Quite the appetizing sight before cake.

  “Well hello, Dolly!” Dad’s putting on his best Louie Armstrong routine. He finally lifts the phone up so that I can see Mom hanging behind him, waving. “This is your Dad, Dolly.”

  Sometimes I wonder if my fate as a dating consultant was sealed when Dad decided that ‘Hello Dolly’ was my song. That musical and I are a match made in matchmaking heaven.

  “Hi, baby,” M
om says, rubbing her forehead. “Please stop Dad from singing.”

  “How’s my bella principessa?” Dad asks. He grabs the TV remote and points it, muting what sounds like a baseball game.

  “Eating some princess cake.” I grin at the waiter as he delivers my weight in pastry. Man, I’d love to mash my face into this beauty. Growing up half Italian, all emotions are best expressed through food. Dad cackles.

  “You didn’t get the cannoli? What kind of child did I raise?” His voice booms, which is Dad all over. He finally retired from his own law firm, where he was the canniest bastard on Long Island for thirty years. He’s a brash and brazen guy who isn’t afraid to curse you out or challenge you to a fistfight in the parking lot. On the other hand, he also keeps my and my sister’s childhood rooms as shrines to us, and bawled when Lady Sybil died on Downton Abbey.

  “She gets the good taste from my side, darlin’,” Mom sighs, finally taking the phone from my Dad. “Dahlia. How are things?”

  “Going strong and steady. I just finished meeting with a client.” I take a forkful of cake and stuff my face with it. Witness me, mother. Witness thirty plus years of perfection and sugar.

  “And how’s your personal life? Going any smoother?” She raises that perfectly plucked brow. Mom’s been getting more and more concerned since I turned twenty-five still single. It’s not that she thinks I can’t live my life without a man; she runs her own stationary business, so she’s fine with women working. But she reminds me, gently, always gently, that work isn’t nearly as important as family.

  Which I do know. But I can’t settle for something that’s not right, can I? Especially when I had the most mind blowing sex of my… you’re on the phone with the parents, Dahlia.

  “I, ah, hey, my moscato’s not going to drink itself.” I take a big sip. I’m sure this all looks really healthy at a quarter to noon. Sometimes I need to indulge. We all do.

  “I just don’t want you to be unhappy.” Mom’s winding up for the When I Was Your Age I Had Just Had You speech, and while I’d like to talk about the ticking clock and the merciless hand of fate and loneliness, I’m not up for it at this particular moment.

  “I’m never unhappy when I have cake.”

  “What about wedding cake?”

  “Wow, did you honestly just segue with that? I’m impressed. You lose two points for the slightly clunky delivery, but we here at the Rossi Family award you a solid eight for that reach. It was most impressive.”

  “Don’t be a jackass, Dolly. Mom deserves a nine at least.” Dad’s turned the ball game back up, and is now swearing at someone, anyone. It’s his hobby, yelling at professional sports. Everyone needs something to fill the days. Mom gives me that ‘loving yet worried’ look yet again. Well, sorry Mom. I didn’t have the serendipitous meet-cute that you and Dad had when he backed into your car and you attacked him with a hammer. Much fun as that is to reenact at family gatherings, I don’t believe in fate. I believe in making things happen.

  Like right now, when I get a reminder on my digital calendar that my date with Jack Carraway is still set for tomorrow at whaaaaaaaaaaaa.

  “Baby, what’s wrong? You made a noise.” Mom looks shocked. “Like someone squeezed the air out of you.”

  “I’ll, ah, call you back,” I say.

  “If you can wait till the top of next inning, that’ll be perfect,” Dad yells. I hang up, and stare at that notification. Me. And Carraway. On a date.

  Date. The word blinks at me, like a blinking thing that has a billion dollars and great hair.

  When did that happen? How?

  Then, in a swirling haze of martinis and endorphins, it replays itself. We’d just, ah, disentangled from one another. We were lying there, still catching our breath, and I…

  I. Asked. Him. Out.

  So. I blew up the whole ‘never have sex upon just meeting someone’ rule. I jettisoned the ‘have him ask you on the date’ rule. Why is Carraway doing this, anyway? He got what he wanted. Jesus, maybe he was trying to salvage my hurt feelings. I probably don’t even have his number. I check my phone, and nope. No Carraway. No Jack. Just as I’m relaxing, I feel my stomach knot. I check my records one more time, and yep. There it is.

  McGee, Billionaire

  Tentatively, I press ‘call’ and listen. One ring. Two rings. He’s not going to pick up. This looks too desperate.

  “Ms. Rossi. How are you?” He sounds warm, charming, relaxed. Quick, hang up, burn the phone, and never speak to him again. Foolproof plan.

  “Are we still on for tomorrow? Hi, by the way.” Flawless and smooth, Dahlia.

  “Hi. We are.” He pauses. Then, “You want to know where we’re going, don’t you?”

  “I didn’t keep meticulous records. Like I said, I—”

  “Never do these kinds of things, I know.” Then, his voice getting even lower and his tone more amused, “It’s one of the things I liked about you.”

  Oh, one of the things? And not all of said things are my boobs and my getting naked in twenty minutes flat? That’s one of the strangely nicest things I’ve ever heard.

  I’ll take it.

  “Well, I like that about me, too. And you. You, too. Where did I say we were going?”

  “How about I surprise you?” He hasn’t run for the hills yet, which means he’s either remarkably persistent or a sucker for punishment. “That way, it’s like I suggested the date. I know that’s on your list of rules.”

  “I didn’t happen to give you a hardcopy, did I?”

  “It’s sitting on my desk as we speak.”

  “Isn’t the Carlyle stationary nice?” I feel like walking into the kitchen and asking the Damicos to mercifully end my life by baking me into their next cake.

  “That’s an odd thing to appreciate, but yes. The paper’s very, er, creamy?”

  “My mother runs a stationary business. She—never mind. Tomorrow. Dinner?” I find myself nervously biting my knuckle. It couldn’t be that I want to see this man again, not after I blew up all my rules and he clearly showed how not into rules he is. That’s not sexy at all. Oh no. Is it warm in here, or is that the moscato talking?

  “I’ll have my car pick you up at eight.”

  “Do you need my address, or do you already have it? I didn’t give you my bank statements while we were naked, did I?” The things you’ll ask when not-dating billionaires.

  “I could have used this opportunity to test the new espionage drone system I’m developing for the US government, but sure. Giving me your address works, too.”

  I rattle it off, then pause. “Since we’re going about this whatever it is we’re doing somewhat backwards, mind if I ask a question? An honest one?”

  “While I prefer dishonest ones, I’ll make an exception here.” Ah, he’s teasing me, the bastard. I thrust my shoulders back and perk out my boobs. Two can play the sass game, good sir.

  “You don’t seem like the kind of man who returns to the scene of the crime.”

  “I don’t view dating beautiful women as illegal, but I see your point. Why would I, a charming and slightly eccentric billionaire, want to see a woman after—”

  “Experiencing the ‘little death’ with her, since we’re speaking the crime lingo. I do wonder.” I take a chug of moscato, because that is how adults do in these kinds of conversations.

  “Well.” He pauses, and it sounds like he’s smiling. “Maybe because I don’t get to enjoy this type of phone call all that often. I’m amused.”

  Oh, I amuse you? Like a clown? Prepare for the full on Italian American stereotype of Joe Pesci going berserk in Goodfellas, except this time he’s in heels. Let that horrifying image sink in. You’re welcome.

  “It’s nice to be amusing, especially in bed.” I roll my eyes, and Jack tsks.

  “There was nothing amusing about that.” He gets steely, sexy voice now. I bet his eyes are smoldering blue; this is the kind of voice for that type of look. “In fact, I take that part very seriously.” While my brain stru
ggles to reboot itself for a witty retort, especially as I’m seriously turned on and getting more so, he laughs. “See you tomorrow, Ms. Rossi.”

  “Bye, Jack.” No formality here, buddy. That makes him laugh, and we hang up the call. I start shoveling princess cake into my mouth, my heart racing. It might have to do with all the sugar I’ve just consumed, but enough about that.

  I have a date with a billionaire tomorrow night, and it worries me that I’m this excited about it.

  6

  Dahlia

  There is no one on planet Earth less suited to romantic dress shopping than my best friend, Chelsea. But we’d promised to get lunch together, and between the butterflies in my stomach and the metric ton of cake I shoved down my throat, I don’t think I’m in a great place for lunch right now. Which Chelsea is perfectly fine with, as it turns out.

  “I’ve started an herbology treatment,” Chelsea tells me as we swing into Bloomingdale’s. She looks as appropriate in a department store as Edward Scissorhands might in a Lisa Frank dreamscape. Even though it’s office hours and she’s dressed for work, she still manages to get away with dark purple nail polish, extensive eyeliner, and sandals that a Tibetan holy man might wear while climbing the mountains. Chelsea on her weekends is something else to behold. She’s awfully fond of ponchos.

  “Herbology, huh?” I scan the sales racks, looking for something elegant. Something casual. Something slinky. Something cute. So, like, five dresses in one. Not that I’m putting any thought or care into meeting Mr. Jack Carraway for dinner, oh no. No. No way. I want to waltz into the restaurant and show him how much thought I did not put into this, with matching shoes and perhaps a purse and maybe a wrap, because it might be chilly. It might be chilly on this date I do not care about.