The Trouble With Bachelors (Windy City Bachelors Book 1)

by Caitlyn Blue

  Gabby and Sarah exchange glances while Brynn shakes her head in dismay.

  “You’re not mad?” Gabby asks.

  Not yet. “Let me see the text.”

  It’s a single word. Sure. Finally I’m breathing easier. A knot had formed in my chest without me noticing, and now it dissolves. But before I let my cousins off the hook, I read Zach’s text before it.

  I don’t want those girls. I want you. Meet me at Gillies at eight.

  The thing about typed messages is you can’t pick up any subtext from tone of voice or facial expressions. If he’d said something like that to me in person, I would’ve had a better sense of what I was agreeing to.

  Is he being flirtatious? Serious? Neutral? Have I agreed to a hook up or the start of something? Needless to say, at the moment I don’t honestly know which of the two I prefer.

  “What are you going to wear?” Gabby asks.

  “Duh,” says the adorable, high school drama teacher. “Something totally slutty.”

  “Why would you go there?” Brynn jumps to my defense before I can open my mouth. “There isn’t a single slutty thing in her closet.”

  Sarah nods. “That’s why we’re going shopping in Gabby’s.”

  “I don’t have anything slutty.” Gabby looks at Sarah.

  “You know, the stuff you wear when you work at the restaurant,” Sarah says.

  “That’s not slutty,” Gabby protests. “Some of it might be low-cut and short and snug, but it’s all tasteful.”

  We’re all pretty similar in height and size with me on the curvier side, and it isn’t unusual for us to raid each other’s closets. Well, mostly we raid Brynn’s closet because she has the most sophisticated taste and the money to indulge it. Sarah’s wardrobe consists of slim-fitting pants in neutral colors, solid color blouses and sweaters. I enjoy pairing vintage pieces from the fifties with modern styles. It gives me a look that’s classic, feminine, and a little funky.

  “It’s all a matter of perspective,” Brynn says. “For a downtown restaurateur it’s normal, for a suburban antique store owner, it’s slutty.”

  While I see Brynn’s point, I’ve never borrowed any of Gabby’s work clothes. She’s built like my other three Callahan cousins, slender with small breasts and big feet. I’m curvy like my mother and probably fifteen pounds heavier than the weight I have listed on my driver’s license. The necklines that look sophisticated and edgy on her will scream look at my boobs on me. I need to wear an outfit that says: I’m available but not easy. Whatever that looks like.

  “He’s expecting me,” I say, “not Emma two point O.” Ignoring my cousins’ stubborn expressions, I hand Brynn the discarded decorations. “I will meet Zach, but I will go in my own clothes.” With that declaration, I head for the stairs.

  Both Gabby and Sarah stalk after me. I’m pretty sure they intend to dress me in clothes that will give Zach the impression I’m like all the other girls he dates. Or that I want to be. Don’t get me wrong. I’m tempted by the idea of hooking up with Zach. He’s been my secret crush for a long time. And that’s the problem. You don’t get over a decade-long infatuation with a days-long fling. At least, I don’t.

  It takes my cousins less than half an hour to bully me into what they deem the perfect outfit and despite my initial resistance, I can’t help but grin at my reflection. Maybe, my cousins are right and Zach needs a clear picture of what he’s been missing all these years. If so, this is definitely the look that will do it.

  4

  Zach

  At quarter to eight, I push open the door to Gillies bar and am hit by an unfamiliar rush of nostalgia. It’s not like me to look back. I’m the guy with my eye on the horizon. I’m obsessed with all things bigger, better, faster and newer. So why am I meeting my ex-girlfriend’s little sister in the neighborhood bar three blocks from where we grew up?

  A better question might be what the hell is with this infrequent eye twitch that started as soon as I suggested we grab a drink? I can’t possibly be nervous or anxious about meeting Emma. We’ve known each other forever. She’s familiar. A friend.

  I met Emma my junior year of high school. We were in the same speech class, and when the teacher put us together for a project about contamination of drinking water, I wasn’t exactly thrilled to be matched up with a freshman. But in terms of the class, it was the best thing that could’ve happened to me. As shy and awkward as Emma appeared most of the time, when she stood in front of the class, some sort of crazy metamorphosis happened. She became charismatic and inspiring.

  And today, when she pulled that condom out of her purse, it was speech class all over again. Only it wasn’t just admiration I’d felt for her. My body had lit up like a fireworks display on steroids. It was unexpected and I’ve trained myself to discover the potential in anomalies. Some of my best marketing ideas have come from embracing the unpredictable.

  “Look who’s here,” calls Chuck Sievers, Gillies’s owner. He’s behind the bar the way he’s been every night for the past thirty years.

  “Hey, Chuck.” I don’t need to ask how he’s doing. The bar is packed, so business is good.

  “What brings you back to the neighborhood?”

  I don’t come back often. My preferred stalking ground is the downtown bars near my renovated condo which serves the dual purpose of home and office north of the loop that overlooks the river.

  “I’m meeting Emma.”

  I don’t need to add a last name. Everyone around here knows who Emma is. Her family’s antique store is across the street and down the block.

  “Callahan?”

  I nod, unsure what to make of the amusement that flashes across the faces of everyone eavesdropping on the conversation. “She and I are standing up for Julie and Paul. We have…stuff…wedding stuff to talk about.”

  As if that explains everything, the group gives a collective nod and returns to their separate conversations. Even though I’m early, I weave through the tables, looking for Emma. She hasn’t yet arrived. I grab a booth in the back that has been recently vacated and slide in. A waitress stops by and I scan the list of beers, not surprised to see three of Paul’s Evolution brews listed. This neighborhood takes care of its own. Some people—most people around here—find that comforting. For me it’s claustrophobic.

  I’m halfway through my beer by the time Emma pushes through Gillies’s front door. She smiles and greets several people. Chuck points toward the back where I’m sitting. I watch her approach, noting she’s changed her clothes. I like what I see. Over-the-knee black leather boots and a black dress that hugs her abundant curves. It’s unseasonably chilly for early April and she’s wearing a leather bomber jacket with a bright blue scarf as her only splash of color.

  “Hey,” she says, sliding into the booth opposite me. Her luxurious brown hair is pulled back in a low side knot with wavy tendrils framing her round face. Red lipstick draws my eyes to her mouth. She’s not smiling. “Look, about earlier.” She puts her hands flat on the table and leans forward, all earnestness.

  “When earlier?”

  “The texts. I didn’t agree to meet you here. Sarah did.”

  I have no idea what she’s getting at. “I’m pretty sure that was your number I was texting.”

  “Oh, it was.” She unwinds the scarf from around her neck, exposing the hollow of her throat and a silver necklace displaying the word believe in flowing script. “And most of the responses were mine, but when you offered to meet here for a drink, Sarah had my phone and agreed for me.”

  “And you’re telling me this because you didn’t want to come?” Disappointment hits me hard.

  “It’s not that. I just didn’t want you to get the wrong idea.”

  I frown. “And what idea is that?”

  “That I agreed to meet you because I intend to sleep with you.” She stares at the scarf in her hands as she plucks at a loose thread.

  “Okay.”

  I’m not sure what just happened, but suddenly the a
nxiety I was feeling earlier fades. But my disappointment lingers. Did I really expect tonight would end with Emma and me in bed? No, not really. If I had, I would’ve chosen a bar closer to River North where I live because I’m pretty sure she’s not going to invite me back to her place with all her roommates there.

  “Sure,” I continue. “Whatever.”

  She looks relieved now that she’s cleared the air. Her white teeth flash in a grin. “You’re drinking beer? Gabby tells me you’re a whiskey guy.”

  “When the good stuff’s available. Besides, I like to support Paul whenever I can.”

  “That’s nice of you.”

  My mouth goes sawdust dry as she peels off her jacket and reveals the insane curves of her breasts bared by the dress’s plunging neckline. Holy shit. Heat sears through me, setting my skin on fire.

  “He is my best friend,” I say.

  I tear my gaze away and swallow a large gulp of beer. How the hell am I supposed to keep my eyes to myself all night? Ah, shit. I polish off what’s left in my glass and signal to the waitress.

  “He’s lucky to have you,” Emma says, oblivious to my torment.

  Keeping my gaze above her neck, I study her as she chats with our waitress. I’m not surprised they’re friendly. One thing about Emma, she’s great with people. Always has been. She loves to talk, but more importantly, she listens with her full attention. During the days when I was dating her sister, she used to make me feel like what I had to say was really interesting. I sure didn’t appreciate that about her back then.

  “So, how are you doing?” she asks as soon as we’re alone again. “We didn’t get a chance to talk at the shower.”

  “Busy,” I say. While this is true, it’s also my go-to answer. Most people ask that question but don’t really care about the answer.

  “Doing what?” She sets her elbows on the table and props her chin on her hand, pinning me with her warm brown eyes.

  I sit back and give her a half shrug. “Work, mostly. I’m doing several webinars every week, and I have more consulting work with start-up companies than I can handle.”

  “Are you dating anyone?” Emma asks as the waitress sets down her Shiraz and another beer for me. “Thanks, Jess.”

  Jess flashes Emma a grin and heads off.

  “Nope,” I say. “I’m all yours.” And to my surprise, I mean it. My last long-term relationship was two years ago and lasted about six months.

  “You’re assuming I want you.”

  “Why else would you be here?”

  She cocks her head and regards me as if she’s unsure what I’m up to. I hope when she figures it out, she’ll let me know, because right now I’m swinging at the end of a rope with no idea how I got here.

  At long last she lifts her glass and touches it against mine. “We’re just two old friends getting together for a drink.”

  “Except we never had the chance to be friends.”

  “No,” she agrees, sipping her wine. Her eyes narrow as she watches me. “You probably didn’t know, but I had a crush on you.”

  I smirk. “It was pretty hard to miss.”

  “You never noticed. I’m pretty sure the whole time you dated Julie you didn’t even know I existed.”

  “Oh, I knew. You were the pesky little sister who we had to ditch if I had any hope of getting your sister to make out with me.”

  She wrinkles her nose. “And you were the first guy I saw naked.” It’s adorable the way she claps her hand over her mouth and regards me with big eyes. “I didn’t mean to tell you that.”

  And then her words register. Holy shit. “Tell me you didn’t watch us.”

  “Yuck.” She shakes her head. “No. It was that story you told today. About the time we all went up to our uncle’s cabin and you and Julie went skinny dipping.”

  “I don’t remember you being there.”

  “I snuck out after you and watched from the bushes.” Her laugh is self-conscious and charming. “I was such an idiot.”

  “Sounds like you were more curious than anything else. Nothing wrong with that.”

  Her head starts to shake before I’m done speaking. “Julie and her friends fascinated me. It seemed like there was way more than two years between us. Then in high school, the difference became so much more obvious. She was on the dance team and ran cross-country. Meanwhile, I was a member of the speech club and Harry Potter club. She dated the captain of the soccer team and I never made it to a single school dance.”

  “So you were a late bloomer.” I’m trying to make it sound like it’s no big deal, but from her frown I can see all I’ve done is annoy her. As an only child I don’t really get this whole sibling rivalry thing.

  “It’s hard to bloom when your sister is one of the most popular girls in school.”

  “It must have gotten a little better after she graduated. I heard you went to state in speech senior year. That’s not exactly easy to do.”

  “I’ve always been pretty good at talking.” She sits back and regards me with something like surprise. “You know I think this is the longest conversation you and I have had in years.”

  I’m pretty sure she’s right. How is it we’ve been around each other these last few years but never spent any time talking? I suppose what happened between her sister and me has something to do with it. Paul told me once that Emma took my breakup with her sister really hard. I felt bad about that. While I dated Julie, I thought of Emma as the little sister I never had.

  “You haven’t been around the old neighborhood much,” she continues. “Paul said you couldn’t wait to get out of here. I’m actually a little surprised you kept in touch with anybody from high school.”

  “I probably wouldn’t have if it wasn’t for Paul. He’s pretty hard to get rid of. Ask Julie.”

  “In a little over two months it will be even harder for her because she’ll be married to the guy.”

  Emma’s smile is potent and I’m struck by sudden breathlessness.

  “Does she know what she’s getting into?” I let my eyes widen in mock concern.

  “They’ve been dating for six years,” she says. “I would think so.”

  “Okay, so we talked about me and we’ve talked about high school. How are you doing? How’s business at the antique store?”

  Three generations of Emma’s family have run Cedar Park Antiques. It was started by her grandmother and great aunt in the early sixties and then passed down to her mother. Soon it would be Emma’s turn.

  “Things are great. The store’s doing really well.” She goes on to talk about the new direction she’s taking with the inventory displays, but my gaze and mind are having a hard time staying focused. “What?” she demands a few minutes later.

  “Would you mind putting your scarf back on?” I say, rubbing my eyes. “Those are beautiful and terribly distracting. I’m having a really hard time hearing what you’re saying.”

  Damn if her grin doesn’t have the slightest hint of evil in it. Of course she dressed like this on purpose. She had to know I’d be completely blindsided.

  “Better?” she asks as soon as she’s covered up.

  “Yes and no.” While my brain is no longer fogged by lust, my thoughts continue to linger over how perfectly formed her breasts are and how much I’m dying to get my mouth on them.

  “We should talk about the combined bachelor/bachelorette party,” she says, guiding us to a safer topic. “I think we could talk them out of it if we come up with a really bad idea.”

  I’m not sure I want to talk them out of it. I like the idea of Emma and I planning a combined party. Mostly because I like the idea of spending lots and lots of time with Emma.

  “What sort of bad idea did you have in mind?”

  “A museum outing? We could go to the Museum of Science and Industry. It’s pretty cool.” That she’s able to say this with a straight face is pretty impressive.

  “Bad. Okay, I get it. How about an evening of bowling and karaoke?”

  She
shudders. “Oh, and we could add a scavenger hunt.”

  “Now that actually sounds like fun.”

  “Not if we make everyone pair up and we get to choose the teams.” She has a wicked sense of humor that I find damned appealing. “Or we could do a game night. Exploit Julie’s competitive spirit.”

  Her sister is more than just competitive. She’s cutthroat. “She might actually go for that, and no one is going to have fun playing Pictionary or Balderdash with her.”

  “We’ve moved on to no one wanting to play Exploding Kittens or Telestrations with her.”

  We each have another drink and I try to make mine last so she’ll feel obligated to stick around. But eventually she gives me a clear signal that it’s time to go.

  I find myself reaching for her hand as we exit Gillies, but all my fingers find is air. She’s sidestepped away, skittish and on the verge of bolting. Moving decisively, I snag her arm and step close.

  “Where’s your car?” I murmur near her ear.

  She looks up at me with wide eyes. “Over there.” She points to the far end of the lot, a dark corner where the streetlights don’t reach.

  “Come on.”

  “You don’t need to walk me.”

  “What sort of gentleman would I be if I didn’t escort you safely to your car?”

  “Wait.” She leans away and stares at me in feigned surprise. “You’re a gentleman?”

  “Always.” The next few minutes would determine that.

  We reach her car, a ten-year-old Subaru Outback. “This is me.” She has her keys out and is ready to make a fast exit.

  “Thanks for coming out tonight. I had fun.”

  “Me too.”

  A light breeze blows strands of her soft hair across my knuckles as I cup her cheek. “Feel like doing this again?”