by Hollis Wynn
“I’ll think about it,” I say and close my laptop. This conversation is over.
Mr. Boring
Capricorn, Cupcakes & Cocktails
I had a date last night. Not a good one, but a date, nonetheless. Ciara dubbed me the queen of first dates a long time ago, and it appears as though that hasn’t changed much. She no longer gets excited and said she’ll save the excitement for date number two.
I don’t care—what Chicago girl does? Living in a city as expensive as Chicago, it’s nice to have dinner and drinks paid for by someone else. Don’t get me wrong, I can afford my lifestyle, but it’s still nice to have someone else do it. Plus, I’ve been to all kinds of places I wouldn’t normally go. As Carrie Bradshaw says, “I like to see my money in my closest.”
Last night’s date was boring. Flat out boring. He wasn’t bad looking. Probably close to six feet tall, dark hair and brown eyes. His hair was a bit mussed, like he spent the day running his hands through it because he had issues he couldn’t shake. At his request, I met him at Bar Louie. Who takes a woman they want to impress to Bar Louie, in a city like Chicago? He needs a better wingman because the guys I normally date wouldn’t be caught there.
I have a set of rules for dates. They came about after a date of monumental disaster, and I’m pretty good at keeping them. Plus, I don’t tell the guys I have rules. If they don’t know them, they won’t break them—unless that’s just who they are. Then I know before we get too far down the road.
As a single girl in the big, bad city, I always need to be safe. First, I send Birdy a text of the time, place, the name of the guy and a photo from his profile.
Oh crap! Did I forget to mention the online dating? Yeah? Well, we’ll get back to that.
Second, I always take a car service. No way I’m allowing a guy to pick me up. Not happening.
Then I text her when I arrive and when I am home. The goal is less than two hours and if she doesn’t hear from me by then, my phone blows up. Thankfully, she’s only had to make those calls a handful of times.
But back to last night—Dan was boring. I should have known by his name and what he was wearing when he arrived. His button-down shirt, vest and khakis didn’t lead me to believe he was going to be super sexy. However, I haven’t had a date in a while, so I decided why not?
I should know to listen to my gut. That chick knows what’s going on.
Making all the decisions on a date is less than stellar. Men, remember to be assertive. I could date myself if I wanted to be the decision maker, and I don’t want to do that. People will begin to talk if they hear me say I’m dating myself.
Until next time,
Searching Sterling
Three
My father is a bit of a tyrant today and I’m not sure what bug crawled up his ass, but he needs to extricate it pronto. Days like this make me want to pull my hair out—or crawl in a hole, never to return.
My email is full of passive-aggressive notes that I’m refusing to answer. That’s the one perk of being the boss’s daughter. I will not allow him to treat me badly.
I hang up the phone and see a new one pop up in my email. I read it out loud and groan.
“Make sure to follow up on the Tag account and bring me the file for this week’s potential clients.”
I swear you’d think he would remember that I drop the list on his desk every Friday before I leave. “Can’t you wait a couple more hours?” I mumble to myself as I slide into my shoes and head to the file room.
It doesn’t take me long to find what he wants and drop them on Chari’s desk. “Here ya go,” I say as they make a loud plopping noise. “He’s in a mood today, so I’m not going in there.”
I roll my eyes and step away when she laughs.
“That’s the damn truth. I’m going to wait until he goes to the bathroom, then put these on his desk with this sticky note of what time you dropped them by.”
I chuckle. She can get away with anything—unlike the rest of us. Being my mom’s best friend, we laugh at the things she says to him—things no one else would dare say.
A few hours later I check my watch and realize it’s quitting time and I need to pick up some things for book club tonight on my way home.
When I finally make it home, I kick off my shoes and drop my bag on the bench as soon as I enter my apartment. Then I head into my bedroom, unzip the side of my dress, and pull it off before laying it down to air out a bit before I decide if it needs to go to the dry cleaner.
My favorite holey sweatpants and oversized T-shirt are laying on the bed and I put them on and pull my hair into a messy bun before heading to the kitchen for a cocktail and dinner.
Chicago has some amazing restaurants and there is always something new popping up. Don’t get me wrong, I love to eat out and explore as much as the next person, but most nights during the week I choose to make dinner. It gives me some time to relax and reflect on my day. Plus, dining out is much more fun when I have someone else to talk to, other than my multiple personalities.
So, tonight is grilled salmon salad and a citrus martini which I eat while checking the dating app. Hmm, five new matches. I swipe right on two profiles right off the bat. One looked barely eighteen, and the other had to have been at least seventy. That leaves swiping left for three Mikes. Now to decide which Mike to go out with first.
First up on the review is Mike Ryan, the pilot. He appears to have his shit together. Stable job. Good looking. Health conscious. Downfall—he travels four days a week and is in a different city every night. He’ll probably be fun to hang out with, but my gut says he’s got a woman in every city and I’m not looking to be a number on a scorecard.
Next up is Mike Montgomery, the lawyer. He’s from Texas, has an accent, and is super tall. All of those are good things for me, except the lawyer part. I’ve already been down that road and they tend to be narcissistic workaholics. However, since I’m not one to judge a book by its cover, I’ll give him a chance.
Last, but not least on the list is Mike Williams, the CEO. Based on his profile he wears a suit well, has most of his hair and a roman nose. According to his details, he’s almost six feet tall, which in my experience means he’s actually closer to five feet nine. I’m not sure what he’s the CEO of, but I’m willing to give him a chance to win me over.
I down the martini and pick up the pencil that sitting next to the piece of paper with each of their names written on it. I close my eyes, using the pencil to circle a name on the paper.
Pilot Mike for the win. Let’s hope this isn’t the disaster that the last one was.
The Mikes
Capricorn, Cupcakes & Cocktails
Oh, snap! I tweaked my profile and added a couple of newer pictures and BAM, men are coming out of the woodwork. A pilot, a CEO, and a lawyer top the list. The best part—they all have the same name. Welcome to a world of Mike’s. Not Michael or Mickey, just Mike. I’m going to have to give them nicknames so I can keep them all straight.
I have narrowed down over thirty messages to these three—Mike, Mike & Mike. I didn’t know dating was a full-time job, but it seems like it considering the time it takes to weed through all the crap. From dick pictures, to invitations to dinner with their mothers, and even a married guy who wants me to be the third. This crap is crazy!
It’s not going to be long and I’m going to run into one of my work husbands while I’m on a date, and that’s the last thing I want to deal with. These guys already think they should have access to me whenever they want, but I’m not too keen on them being part of my personal life.
Speaking of work husbands, they’re yelling at each other again—time to go play referee.
I’ll be back after my next date.
Until next time,
Searching Sterling
Four
I close the page with a smile and blow my whistle at the guys. Half a dozen heads fly toward—mouths hanging open.
“Stop it. You’re grown ass men! Act like it,” I s
ay sarcastically. I can see the bravado letting go as they stare at me. “Go to the gym and work it out, but don’t act like children in the middle of the office.”
There is a cacophony of mumbles and grumbles from them as they get up and make the way back to their individual offices. Most days I’m glad we have the open space between the offices for everyone to chat and discuss, but this is bullshit.
Sitting at my desk checking my email, I hear Baker ask, “Are you free this afternoon?”
I check my desk calendar. “Other than managing you guys, my schedule is pretty open. Why? What’s up?”
“I have a meeting with a new client, and I thought you’d like to attend since they’re in fashion.”
I clue into the word “fashion” and decide that it would be worth attending. I catch Baker looking at my phone, which has the dating app open, and I flip the phone over so he can’t read anything more than he already has.
I’ve been chatting with Pilot Mike and he seems decent enough, but we aren’t meeting until next week because he’s on a long trip overseas.
“I might. When is it?” I ask him. Knowing how these guys operate, the meeting will be in the next ten minutes.
“Thirty minutes? My car is pulling up now,” he responds.
Looking down at my outfit, I realize I have on one of my old favorites: navy blue fitted crepe dress with a side slit and red peep toes. It’s beautiful and fits my body like a glove, but it’s not fashion forward like I would prefer to be for a fashion house meeting.
“Fine,” I say with a sigh. “But a little more notice would have been nice.”
“I’ll meet you downstairs in a few minutes. Here is your copy of the file.” Dropping the file on my desk, he winks before turning around and heading back to his office, completely ignoring my comment.
I shoot Chari an email and let her know I’ll be out the rest of the afternoon before grabbing my bag and the file. A quick stop in the ladies’ room to check my makeup and apply some lipstick, and I head down to meet Baker.
As soon as I exit the building, he opens the car door for me and places his hand at the small of my back leading me into the car. I try not to squish my face in confusion as to why he’s helping me into the car instead of the driver, but it’s not working.
SEI sits in the middle of downtown Chicago, where the buildings are enormous and cast shadows on the streets. When I first started working down here, I was intimidated. Now, on the days the shadows aren’t out, I feel like something is missing.
Baker slides in next to me, widening his legs and leaning back. A smile graces his face and I look away as the butterflies flutter about in my stomach. I never used to get nervous around him—now, the nerves are front and center. In an attempt to get myself together, I reach in my tote and pull out my phone to check email.
“Don’t you ever take a break from surfing the web or reading a magazine?” I know he’s teasing me, but I’m pretty self-conscious about this topic, because I never want my father to think I’m slacking off.
“Reading magazines? You have no idea how much work I do,” I spout back.
He moves closer to me on the seat and responds, “Enlighten me.” His voice is deep and low, with a rumble that echoes as he speaks.
I sigh and for the next five minutes, dive into the details of my work.
“That’s more than I do,” Baker says, laughing.
I arch my brow and nod in an I-told-you-so way. “But when I’m not at SEI, I’m either at the bookshop or hanging out with my book club and friends. I’ve been known to create some wicked good cocktails and even a cupcake or two.”
He smirks and his eyes grew openly amused. “You’re a witty little thing, aren’t you?”
“Little?” I gape.
His grin widens, and he’s never looked so sexy. I’ve got to get out of this car soon so I can breathe. It must be the confined space that’s causing my heart to race and my eyes to stare at his lush, pink lips.
The car comes to a halt, and he opens the door, exiting while I try to control my heartbeat. Then he’s around the other side, opening my door. Here we go.
Though the firm is high end, the meeting is pretty standard. A review of contracts, discussion of particulars, and confirming a start date is less than fun. I try to stay focused on Baker since he introduced me as an associate; I don’t want to sit around like a bump on a log. The customer needs to trust us, which in turn means trusting me.
We are back in the car an hour later and Baker insists we stop for coffee on the way back. I won’t ever turn down coffee, especially if someone else is paying.
“So, does your time outside the office include a boyfriend?” He leans into me while we’re standing at a high-top table waiting. The barista calls out his name and he goes to pick them up and sets them on the table.
My mind is reeling and though I know the question is somewhat inappropriate, it’s not as though I don’t like him. I do. I really do.
“Does yours?” I retort. He nearly chokes on his coffee as he busts out laughing.
“I’m not gay,” he says, putting his coffee down and holding his hands up in surrender.
I giggle and take a sip of the piping hot liquid. “I know. But that was funny.”
He smiles at me and shakes his head.
“I don’t have a boyfriend right now,” I answer. But I don’t tell him it’s been years since I’ve had a real boyfriend.
“Really?” He cocks his head as he responds.
“Yes, really. Is it that hard to believe?”
He rakes his eyes up and down me as if he’s surveying me. “Hell yes, that’s hard to believe,” he murmurs.
I take a long sip and swallow, wishing I laced it with whiskey to calm my nerves.
“I mean—never mind.”
“What?” I ask him.
He locks eyes with me before responding, “Moving on.”
Baker changes the subject, and we chat while we finish our coffee before heading back. Once we’re in the car, he turns to his phone, answering emails and ignoring me.
When we’re back at the office, he places his hand at the small of my back leading me into the elevator. As soon as the doors open on our floor, I head straight to my desk, refusing to look back and see where Baker is going.
A few minutes later, he’s back standing in front of my desk. “We should do this again sometime.”
“You say that like it was a date,” I say.
“If that’s what you want—let’s do it.”
I immediately lock eyes with him and get lost. I know he’s teasing me, that’s who he is.
“Okay, Baker Hayes.”
His voice is gravelly when he responds, “I mean it, Red.”
Then he turns and walks away.
Open Eyes
Capricorn, Cupcakes & Cocktails
Today has been LONG & insane. The guys had some issues, and we had people coming in and out of the office all day. Since they don’t plan very well, it means I had to order food, make sure there were enough chairs in the conference room, and play organization queen. Not to mention we were out of coffee, so that meant a quick run to Starbucks. Since the company was paying, I grabbed one for myself.
Between meetings, I spent the day doing expense reports. Have you ever tried to read mileage, dates, account numbers written on tiny receipts while driving down the road? No? Well, try it. I’ve come to guess close enough that I keep a log for each guy, so I can make sure I don’t go backward. The best part of my day was seeing B. He is extremely good looking and equally kind. It’s terribly sad that he’s off limits because we work together. Plus, I’m sure he still looks at me as the kid he met when he joined the firm.
He’s exceedingly thoughtful and anytime he goes out for coffee he brings me one back. That makes him one of the good guys. With the number of men in this office there has to be at least one good one and that’s B. Most of them are married but cheat or divorced with a harem of women or just old and crotchety. Do you hav
e guys like this in your office or am I the only one?
Then there’s B. Six foot four with sandy brown hair, blue eyes and thick dark lashes. The combination of kindness in his eyes and his mischievous smile could melt my panties right off. Though he’s never been inappropriate with me—not even a questionable post it or email. He smiles when he sees me and always compliments my outfits. I did wonder for a while what was up because he commented on my shoes so often, so I asked how he knew so much about shoes. I was surprised to learn that his sister is a fashion designer, so she tortures him at family events. That is a great brother who will one day be a wonderful husband.
The more I let myself type about B, the worse it gets. I have my guys on the dating site, but I’m still wickedly attracted to him, even more than before. He could be just being friendly, but I can’t deny the look he gets sometimes.
Ironically, I keep the horoscope on my desk that I read and convinced me to take the chance on stepping out and doing the online dating. It reads:
If you’re on the quest for love, you must step outside of your comfort zone. This is the time to break free from your protective armor and embrace your ability to love with authenticity. You should no longer allow anyone to discredit you or convince you that you’re on the wrong path. When your detractors notice you living a bold life, enjoying an openness you’ve never had before, they’ll question their own limited visions of love. Drawing on your ethical code will make you more fearless. You’ll be motivated to take a personal risk that has intimidated you in the past—including pursue romantic pleasures. This suggests a sudden love connection is on the horizon for you, Capricorn.