Dating My Best Friend: A Second Chance Romance

by Annie J. Rose

Jay furrowed his brow. “Hey, I’m not that bad.”

  “Come here. I need to give you a hug. I feel like I know you already,” Ollie said.

  The man enveloped me in a warm bear hug, and I could quickly tell why he and Jay got along so well. They were cut from the same cloth, both warm, inviting, easy to get along with. I felt relaxed in his presence like I did with Jay. I hoped to see more of him as time went on.

  “All right, I’ve got hot coffees for now, and a nice bag of ground coffee for later,” Kent said as he came through the front door.

  “There he is! Ollie, this is my new partner, Kent,” Jay said.

  “And my boyfriend,” Quinn piped up with pride.

  “And my honorary best friend,” I said.

  Kent paused. “Wait, honorary? Since when?”

  I thumbed over my shoulder at Jay. “Since this guy kinda swiped the title away from you.”

  Kent snickered playfully. “Man. I’ve been replaced.”

  Quinn scoffed. “And what am I? Chopped liver? I thought you were my best friend now.”

  “Well, does that mean I don’t have a best friend?” Ollie asked.

  “You can be my new best friend,” Kent said.

  “Yep, chopped fucking liver,” Quinn said.

  “Sweetheart, language,” Mom said softly.

  “Oh, you fuckers are really gonna hate me, then,” Ollie said.

  Laughter rose from all of us as Kent started passing out the coffees.

  “Merry Christmas, man,” Jay said.

  He clapped Ollie’s shoulder, and I could’ve sworn I saw the two men grow teary-eyed.

  “Merry Christmas,” Ollie said. “And by the way? I’m glad I’m here. I can’t wait to see the two of you get married.”

  I paused. “Wait, you’re here until the wedding?”

  “I told you he packed way too much for only a couple of weeks!” Quinn exclaimed.

  “I packed to stay as long as I’m needed or wanted. But yes. I’ll definitely be back for the wedding,” Ollie said.

  “Actually, I wanted to talk with you about that,” Jay said.

  I furrowed my brow. “Talk about what?”

  “Uh-oh,” Quinn said.

  “What?” Kent asked.

  “If Khloe doesn’t know, then it hasn’t been approved. That’s how this works,” Quinn whispered loudly.

  “I can hear you,” I said.

  “What’s up?” Ollie asked.

  “Well, Khloe and I have been trying to figure out what to do with her home. She’s got this great little one-story cottage with a basement on the outskirts of town. It’s nestled in the woods. It’s quiet. It’s really a great place,” Jay said.

  I heard where he was going with this. “Yeah, but it’s terrible to rent out. It’s a bit of a drive to get into town. Or to the grocery stores.”

  “But there’s lots of hiking.”

  “And walkways.”

  “And running paths.”

  Ollie grinned. “Are you wanting me to move in? Is that what this is? You’re trying to sell me on a house!”

  Jay smiled. “All I’m saying is that there’s an empty house we don’t know what to do with, a town that has helped me through a great deal, and I’m looking at a friend who could use the same kind of healing power I’ve undergone these past few months.”

  “Plus, I need someone in it anyway. I’m tired of checking up on the place just to make sure it’s okay,” I said.

  “And it would be a great place for you to finish your recovery. Much better than that dinky old apartment you’re staying in.”

  Ollie nodded slowly. “How much is it to rent the place?”

  I shook my head quickly. “Nothing.”

  “Nothing?” everyone asked in unison.

  I giggled as I walked over to Ollie and settled my hand against his arm.

  “I don’t owe anything on the house. I mean, other than property tax every year. Pay that and the utilities, and we can work out everything else at a later date,” I said.

  “So, what do you say?” Jay asked.

  Ollie puffed out his cheeks. “That’s a lot to uh, to take in.”

  I rubbed his arm. “Well, you’ve got time to think about it.”

  “About two and a half months, judging by how much you packed up,” Jay said, chuckling.

  Ollie snickered. “You guys would be willing to do that for me?”

  “Yes,” we all said in unison.

  Ollie patted his hand against my own. “Jay, you got yourself a good one here.”

  I smiled. “He knows.”

  Jay chuckled. “Yeah, I know.”

  “Does this mean we can bust out celebratory drinks now? Because this coffee could use some peppermint schnapps,” Quinn said.

  Ollie pointed at my sister. “That sounds wonderful. What do I have to do to get me one of those?”

  Jay grinned. “Accept our offer.”

  Ollie rolled his eyes. “Well, if you’re gonna twist my arm like that…”

  “Yay!” I exclaimed.

  “So, we didn’t have to haul all of his stuff inside?” Quinn asked.

  Everyone started laughing as Jay and I hugged his best friend tight.

  “Merry Christmas, Ollie,” I whispered.

  The man sniffled. “Merry Christmas, you two.”

  “Oh, and let me know when you have time to talk later. You know, about being my best man and everything,” Jay said.

  “What the fuck? Hell, yeah, I’m gonna be your best man!” Ollie exclaimed.

  As my father started gathering up our coffees to turn them into rich, delectable drinks, I felt my heart filling with warmth. With compassion. With love and support. Finally, I felt grounded again, rooted in a reality that suited me instead of a reality that felt like a play I was forced to participate in. I had an adoring fiancée I woke up to every morning, a house full of family on Christmas, and my fiancée’s best friend moving into my old house.

  “Do you even know how much I love you?” Jay asked.

  I smiled up at him as he blanketed me with his arms.

  “I love you, too, Jay.”

  Piper barked, and I reached my hand down to ruffle her head.

  “I love you too, beautiful. Don’t you worry,” I said.

  It didn’t get any better than this.

  The End

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  Pretend Wife (Preview)

  Chapter 1

  Josh

  “It’s not that I won’t play another stripper if the role is good, but could you at least find me one with some character motivation?” I asked.

  “Listen, Josh,” my agent, Caitlyn, said, “you’re a star. You’re on everyone’s sexiest men list. You know how you got there.”

  “I’m glad Say It with Flowers was such a big hit. It opened a lot of doors for me, but they all lead to movies where I play a stripper or a gigolo!”

  “We have to hope lightning will strike twice. The way America loved you before was playing a well-meaning, dimwitted escort. You can’t just switch from that kind of role to playing Einstein,” she said.

  “I don’t need to play a genius. But, hear me out. Look at the scripts you sent me.”

  “I’ve looked at them.”

  “Your assistant looked at them,” I countered.

  “Okay, Clive looked at them. They’re good possibilities. Mid-budget studio flicks, summer comedies.”

  “The descriptions both read ‘attractive but shallow white male late twenties.’ ”

  “That’s you,” she said, taking a drink from her water bottle.

  “Thanks,” I said with a heavy ounce of sarcasm.

  “Being that guy has made you millions,” she said, “and don’t forget the endorsement we got you modeling men’s underwear in Europe.”

  �
��Yes. But look at this, Caitlyn. If you could get them to write in some motivation for the stripper—like he has a sick kid or something, I’d do that. I’d love to show off my acting chops, and I’ll do that in a comedy. I’ll take my shirt off. I know what they go to the theater to see. But I’d like a little more meat to my part.”

  She snickered. “Your part is what they pay to see. You’re famous for being sexy, not a family man or some self-sacrificing hero. If you want to change the type of role you’re considered for, you have to shift your image. You don’t wanna play the hot, single playboy type? Stop looking like one.”

  “Are you suggesting I quit working out?”

  “No. God, no. Tell me that was a joke.”

  “It was a joke. But can I do an interview, talk about changing directions and going for more mature roles? I know I can get Max to set me up with some late-night show for an interview. James Corden? I love that guy. We could sing!”

  “First of all, your singing isn’t going to get your fans to do anything other than change the channel. Don’t you remember when you auditioned for that Mamma Mia sequel?”

  “I nailed the dancing,” I said grudgingly.

  “Right. It was a musical. You insisted on trying out against my advice. Remember?”

  “Yes,” I said.

  “And I give excellent advice. I’ve shepherded your career from playing a waiter on a soap opera to ten million a film.”

  “Yes, you have. And because you have such good instincts, I’m asking your advice on how to transition to a more mature image. Like where I should do the interview.”

  “You can’t do an interview to announce you are ready for more serious roles. Unless you want to play the stern but loving blue-collar dad in one of those Lifetime movies where the kid has cancer.”

  “That isn’t what I want. I want Bradley Cooper's roles. I know he’s older, but he didn’t start out doing serious stuff. He was in The Hangover and crap like that. He played a raccoon in a comic book franchise for Christ’s sake.”

  “You mean the highest-grossing franchise of all time? That didn’t do him any harm. But my point is, if you want more serious roles, you can’t tell people. You have to show them. This is where you talk to Max about reshaping your image. My opinion is you need to get married.”

  “What?”

  “If you want to play an adult, and you want to project the image of an adult, follow the traditional milestones accepted in middle America. Buy a new house. Get married. Have a kid. Tweet about how much you love your wife. You know how Ryan Reynolds is a catch now? It’s not all Deadpool. It’s being married to Blake Lively and having two adorable kids.”

  “I don’t think she’ll leave Ryan for me. And that would make me a homewrecker. That can’t be good PR.”

  “Tell me you’re joking again,” she said, shaking her head.

  “Of course I’m joking. But I love that you think I’m that stupid. I’m not a moron. I just play one on the big screen.”

  “A sexy moron with a sick body,” she corrected. “Talk to Max about an image overhaul before you ask me for a type of film that’s inconsistent with your brand.”

  “So I’ll change my brand,” I said. “Because I’m not excited about playing a bumbling plumber who stumbles on a heist while pissing.”

  “It was a funny setup. You’ve got full nudity from the back, and because it’s comedy you can get PG-13,” she said.

  I felt tired just trying to explain why it was wrong for me. I was past that. I’d grown up. If I told her that, she’d mention that Adam Sandler grew up and had to make TV movies because he wasn’t cut out for juvenile comedies any longer. That wasn’t what I wanted. But I was a sex symbol, while he was a comedian. Meaning he at least was seen as funny and talented, while I was just blessed with good looks and the self-discipline to work out every day. I sighed.

  “Look, if you do a play—Shakespeare preferably—and you focus more on charity work than on partying, that’s the first step. But really, talk to Max. He’ll tell you. He’s a smart man. He knows you need a reboot to get what you want. And I don’t mean some quickie Vegas marriage. I mean a new house, redecorated for your new lifestyle, in Vogue or Architectural Digest or something. Cute pets—Labs, not potbellied pigs and shit—that can chase after you while you stroll the newly landscaped grounds with your wife in pictures.”

  “That’s very specific,” I said, “but I guess I asked for it.”

  I called Max on the way down in the elevator. The damn thing got stuck again, but only for a few minutes. I keep forgetting to heckle my agent about her unreliable private elevator. Anyway, Max took my call right away, which was always reassuring. At least I knew he was still willing to work with me.

  “Hey, buddy,” he said. He was fifty but he always talked to me like I was his nine-year-old nephew or something. Still, he was the best at his job.

  “Hey, Max. I just left Caitlyn’s office, and I wanted to talk to you about what she said. I’m hoping to do more mature roles—not like Gandalf mature, but serious and dramatic. She thinks the reason I’m not getting those offers is—”

  “Your image? I mean, hell, everyone wants to be you. I want to be you. You’re at every party in Vanity Fair. For the last four years, your name’s been linked to everyone from Emma Stone to the latest Sports Illustrated swimsuit model. Those pictures of you and the Italian girl on the deck of that superyacht—I’d be lying if I didn’t tell you they were PR gold for sexy roles. Nothing but passion and no tan lines anywhere. But if you want Oscar contender films, you’ve got to clean it up.”

  “What am I? A junkie? I haven’t been arrested, no one has died at the club I own, and I never harassed anyone. I was pure as the driven snow even during Me Too!” I said, frustrated, “It’s like I’m being punished for being a good-looking single man.”

  “So you’re handsome, successful, a celebrity—and you feel persecuted? I think before we do image alterations, you may need to go to therapy. Because you’re at the top of the privilege heap. Start slow with charity work. Inner-city kids, the arts, something like that. Then get a steady girlfriend. Someone over twenty-one.”

  “Mimi was twenty-three,” I said.

  “Like I said. She needs to be somewhat close to your age. Ideally someone not in show business, but at least not a model or an actress. That way you seem down-to-earth and avoid the perception that it’s going to be a roller-coaster affair.”

  “I have never had a roller-coaster affair. I have relationships, maybe short ones, but it’s never ugly. We never have to deal with a scandal or a tell-all.”

  “Buddy,” he said, “I feel like you’re wanting a pat on the back for managing to reach the age of thirty without a criminal record or a sexual harassment lawsuit. That makes me feel old and depressed because that should be the norm—just be a decent person to start with. And you are, so it shouldn’t be too hard. There are plenty of guys out there with paternity suits against them and messy divorces and tabloid headlines. You’re ahead of the game by not engaging in any of that. But we are going to have to change your image drastically if you want this shift in roles.”

  “Caitlyn said I should get married.”

  “She’s not wrong.”

  “I had hoped for a more creative and less permanent solution from you,” I said.

  “It’s not the only way. It’s just the easiest way. Redo a house together, coo and cuddle in the magazine spread about your lifestyle being so different and how it’s going to show in your work onscreen. How she’s changed your life. America loves a fairy tale. The only thing studios love more than a fairy tale is a good profit. If you’re trending for being an adoring family man, you’re going to find your name attached to some more heavy-hitting projects. No more alien robots.”

  “So getting married is the short answer?”

  “Getting married is the short answer. The long answer is to do charity work. Get on as one of those goodwill ambassadors and tour impoverished countries talking abou
t land mines or potable water and shit like that. Build a public persona as someone deeply committed to working for the greater good over a year or so with multiple interviews and at least one headline-making donation of your own.”

  “I donate to several charities regularly,” I said.

  “And?”

  “I’ve never publicized it. That’s not why I do it.”

  “It would be wise to align yourself publicly with at least one if for no other reason than to use your celebrity to gain attention and donations for the organization.”

  “I can do that. I’ve never been comfortable getting attention for donating to charities though. It feels like congratulating myself.”

  “Don’t look at it that way. Look at it like someone using his famous face to get people to click through to the foundation web site and make a donation,” Max said.

  “Okay. I’ll look into it.”

  “Let me look into it. Send me a list of your patronages. I’ll have my office contact them to see if they’d like to set up a public appearance at a fundraiser. I expect a yes from all of them unless they’ve already got Angelina Jolie or—no, pretty much just her.”

  “Thank you.”

  “You’re welcome. You don’t have to thank me for doing my job, Josh. But you always do. That’s one of the reasons I took you on years ago when you were starting out. You’ve always been very respectful, which is more unusual than you’d think in this business. Give the marriage idea some thought.”

  “But I’m not dating anyone and can’t see myself falling head over heels in the next month.”

  Max sighed his frustration. “It doesn’t have to be the love-of-your-life-forever kind of marriage.”

  I was starting to understand. “So more like a business arrangement?” I asked.

  “Most of them are in Hollywood. They’re power couples, actresses who marry directors, screenwriters who marry actors, producers who marry other producers…”

  “Oh. Okay,” I said. “I get it now.”

  After I spoke to him, I kept thinking of all those Tiffany bowls I’d bought for weddings in the last few years, the cast and coworkers whose ceremonies I’d attended. How many of those had been sincere and how many were just mutually beneficial arrangements? Max himself had married his second wife, a producer, in Hawaii three years ago. I was an usher. I was afraid to ask him about it. I didn’t want to know. Because somehow, after all these years, show business had just managed to disillusion me even more.