"You wanted to see me, Jerry?" "Yeah." "Come on in." "The 25-year-old genius that runs our magazine is making some more changes." "Please don't tell me we have to use those productivity scooters again." "Hey, Andrew, I need to talk to you about..." "Any idea where the brakes are on..." "No, thank God." "But the new owners are shutting down the Denver office and firing half the staff." "The other half are being sent here." "So you now have an editorial assistant." "I don't need an assistant." "I'm very particular about the way I do things." "I mean, my files are alphabetized, color-coded, and prioritized according to relevance." "That's called OCD." "I don't need an assistant." "I mean, the last guy I had tried to organize my files chronologically." "I mean, chronologically, Jerry." "You've got no choice here." "I got one, too." "His name is Derek." "Yes, Mr. Dunham?" "Ah, hey, Derek." "Hey." "I'm good, I'm good." "You know what, hey, Derek, why don't you close the door on your way out." "Guy scares the hell out of me." "And he's got freakish hearing." "Just trying to do my job." "I love that guy." "Look, they can't force me to have an assistant." "I don't want one." "I don't need one." "My answer is no." "Mr. Carlson, your new assistant is here." "Hi." "I'm Amy." "My answer is maybe." "Hi." "I'm Andrew." "May I ask, where do you stand on chronological filing?" "It disgusts me." "I prefer color-coding and sorting by relevance." "Amy, welcome to the team." "And then someone named Bert called." "Bert's my personal trainer." "He's an artist, and this..." "is his canvas." "Oh, I'll get it." "It's kind of my job." "Andrew Carlson's office." "No, this is not Andrew." "I have a high phone voice." "Hold on, Mr. Richards, let me see if I can get him." "♪ Bum, bum-bum-bum, bum-bum, bum, bum-bum-bum... ♪" "He's gonna have to call you back." "Bye." "You just sang the hold music." "Wait, did you used to work for Dick Bergen?" "Yeah." "How do you..." "You're Amy from Dick's office." "I used to call him all the time when I was a fact-checker." "Oh, my God, I can't believe you're Andy from fact-checking." "Your fake hold music was legendary." "You used to harmonize with it." "Eh." "♪ Ba, ba-ba, ba-ba, bum..." "I used to always do that on the other side." "You couldn't see it." "I'm glad I could see it now." "Hey." "What are you doing?" "I'm at work." "Working." "What are you doing?" "I was in the neighborhood, buying a new humidor, so I thought I'd say hey and grab some office supplies." "You can't just come to my office and take things-- it's stealing." "It's built into the price of the magazine." "I didn't know you collected cigars." "I just have the one." "I'm saving it for a special occasion-- it's a Cuban." "My dad got it for my eighth birthday." "I thought the traditional gift for an eighth birthday was a prostitute." "No, that's 13." "Oh, here, let me help you with that." "Bert, this is Amy, my new assistant." "Bert Lansing." "Andrew's roommate-slash-trainer." "Oh, right." "My boss is your canvas." "I told you to stop telling people that." "It's weird." "Can I get you anything, Mr. Lansing?" "Just a bottle of water." "And a box of paper clips, and enough rubber bands to make a ball that big." "I'll see what I can do." "Wow, she's something." "Yeah." "She's the new laser printer." "Supposedly prints 40 pages a minute." "I'm talking about the smoking-hot girl carrying it." "Please tell me you're getting on that." "That happens to be my assistant, and it's completely inappropriate to date her." "Come on, office sex is part of the American Dream." "Why do you think I put an office in my gym?" "It is unethical for me to think of her that way." "There are entire handbooks written to prevent bosses from hitting on their employees." "Yeah, but those books were written back when assistants were ugly." "Diane, you've done it again." "This tuna casserole is fantastic." "Actually, it's chicken." "Then it might be going bad." "Oh, so, Andrew, I called your office today, and I love your new hold music." "That's something my new assistant does." "You know what else she does?" "She's smoking hot." "All I know is she's great at her job." "Yeah, I bet she is." "How are you making that dirty?" "Job?" "I don't want to talk about Amy, okay?" "You know, this guy is unbelievable." "He's got a ridiculously hot assistant, and he won't ask her out." "That's right, because a gentleman does not dip his pen in the company ink." "Well, you know what, Andrew?" "Janet and I went to the bathroom where we ate." "He's trying to say we met at work." "Yes." "Never been a problem for us." "What about the time you guys got in trouble for fooling around in an empty office at the museum?" "See?" "Your sister doesn't have a problem banging her employees." "I thought we were never gonna tell anyone about that." "It was supposed to be a secret." "I just told Andrew;" "he's my brother." "I should be able to tell him things." "Not secrets." "That's why you call them secrets and not "tell your brother-isms."" "Oh, excuse me." "Hello?" "Oh, I'm sorry, ma'am, I have the wrong number." "No, Jerry, it's me." "I have a high phone voice." "What do you want?" "One of our interviews fell through, and I need something from you by tomorrow to replace it." "I can't write an article by tomorrow." "Well, fish something out you wrote a couple of years ago and rework it." "I'll have Amy meet you at the office." "No, I don't need Amy to..." "Oh, shoot, Derek's coming." "You know, the guy has a tattoo of a scarecrow with no mouth." "That can't be good." "Jerry, wait, I need..." "Ah, well, I got to go back to work." "Is Amy gonna be there?" "Yes, she is." "Oh, yeah..." "You know, I'm not like you." "Every encounter with a woman is not a Barry White song." "My relationship with Amy is strictly business." "The business of "Oh, yeah..."" "Hey, Andrew." "Hey." "Hey." "Sorry about my outfit." "I was on the way to yoga when Jerry called." "Oh, is-is that not what you usually wear to work?" "'Cause I picture you without clothes." "As in, I don't notice what you normally wear 'cause I see you as just another human working person." "Good, because I see you as a human working person, too." "Okay, well, I, uh... get to work." "I need to find a thousand-word article to recycle by tomorrow." "What about that great article you did a couple years ago?" ""Let's Give the Goatee Back to the Goats."" "How do you know about that article?" "I'm a fan of your work." "You're part of what inspired me to become a writer." "This is embarrassing, but it's kind of why" "I asked to be on your desk." "That's not embarrassing." "I'd love to have you on my desk." "Professionally." "Uh, so you want to be a writer?" "Yeah, actually I have a couple of ideas that I thought would be great for the magazine." "Maybe we could grab coffee sometime, and you could read them over?" "Oh, that would be great." "But I'm allergic to coffee." "What?" "Yeah." "I throw up blood." "So... not a good idea." "Uh, but you could e-mail them to me." "And, um, I could forward the best ones on to Jerry." "Wow, that would be fantastic!" "That's really cool of you." "Oh, yeah..." "Oh, what are you working on, Janet?" "Electronic mails to Andrew, revealing my most intimate secrets?" "Look, I tell Andrew stuff;" "he's my brother." "Well, I'm your husband." "Husband-wife trumps brother-sister." "Unless you marry your sister, and then it's a draw." "This is so embarrassing." "There's nothing to be embarrassed about." "I don't tell Andrew everything, just important stuff." "Did you tell him about the time with the sex puppet?" "I'm sorry, I needed to know if it was normal." "Of course it's normal!" "It said so right on the box!" "Doesn't mean I want your brother knowing about it." "He's my go-to person." "Don't you have a go-to person?" "No, we don't have go-to people in New Zealand." "If you got a secret, you tell it to a sheep." "Then you throw it off the cliff." "That's where they get the saying," ""Dead sheep tell no tales."" "Hey, Bert." "Have you seen my..." "Shh..." "Is your cigar sleeping?" "This cigar is almost 30 years old." "It needs to be handled delicately." "Like telling somebody you broke their blender." "By the way, wear shoes in the kitchen." "Wait, so you've had that cigar for 30 years, and you've never found an occasion special enough to smoke it?" "Nope, just never felt right." "Maybe because that cigar is one of the only things my father ever gave me." "Wow!" "Really?" "!" "Well, that and the ability to push my emotions way down where I can't feel them." "That's kind of sad." "Not for me." "So how'd it go last night with Amy?" "Did you put your article in her in-box?" "Nice." "You must have been the funniest kid in fourth grade." "Yeah, two years in a row." "So why don't you just admit you like her?" "Because that wouldn't be appropriate." "Look, do we have things in common?" "Sure." "Do we have a nice rapport?" "Yes." "Did I have a dream last night where the two of us moved to Paris to co-write a cookbook for lovers?" "Maybe." "But there's nothing I can do about it." "Amy." "Hey." "What are you doing here?" "Oh, I called to tell you some good news, and Bert said I should come and tell you in person." "Oh, yeah." "Amy called while you were in the shower." "Thanks, Bert." "I wanted to thank you for forwarding my ideas to Jerry." "He liked my writing, and he gave me an assignment." "Wow, that's amazing." "Oh." "Yay!" "So, what's the assignment?" "To visit the five most romantic places in Chicago in one night." "And the magazine is paying for it." "That's awesome!" "You should invite Andrew." "What?" "Why would she do that?" "You can't have a romantic night by yourself." "I mean, you can, but it's nothing people want to read about." "Okay, sure." "What do you say, Andrew, do you want to go?" "Uh..." "I don't think so." "There's something in the hallway I need to show you." "What?" "Uh... a dead animal." "What is wrong with you?" "You have the chance to go out with a beautiful girl and have someone else pay for it." "Like on my 13th birthday, when my dad..." "Don't tell me the rest of that story." "And I can't go out with her, because it's basically a date masquerading as work." "And she is my assistant." "You find something wrong with every girl:" "she's you're assistant, she works at your favorite coffee shop, she used to be a dude." "That was valid." "That girl had his own fantasy football team." "This girl Amy is the total package for you." "If you don't ask her out, someone else will." "I'm sorry, I have my rules." "Without them, I am nothing." "Okay, fine." "Good luck dating your rules." "Amy, I got good news." "I found someone to go with you." "Bert, I already told Amy I can't go." "Yeah, I was talking about me." "What?" "What?" "Well, since Andrew can't make it," "I'd be happy to help you out." "I spent half my life here." "I'm more Chicago than Mike Ditka's mustache." "Uh, sure." "Why not?" "I can't think of a single reason." "Okay, I'll see you at work." "Buh-bye." "Bye." "So, how's that gentleman thing working out for you?" "Hello?" "Oh, hi, Amy." "Is Andrew there?" "This is Andrew." "Sorry." "Well, look, good news for you, you're my new go-to person!" "But I'm already Janet's go-to person." "Well, I'm going to need you to double up." "She embarrassed me, and now I'm going to embarrass her." "Uh, I don't know if I feel comfortable being in the middle of this." "Did you know, hair only grows on one of Janet's legs." "Yes, and it may or may not run in the family." "Well, here's a good one." "After a few wine coolers, she has an alter ego named Jonathan!" "Yes, Jonathan Gundersen." "I've been his designated driver." "He has a last name?" "has whole family." "I have to go." "Tell me more about the Gundersens!" "Okay, I'm going to head out, if you don't need me for anything else." "Yeah, no problem." "Wow, you look nice." "Oh, Bert and I are going out to research my article tonight." "Uh, yeah... about that." "I don't know if that's the best idea." "Uh, you know, he's not really a guy you bring to a romantic place." "I mean, maybe if you were writing an article about the top five topless steakhouses in Chicago." "Are there really five of those?" "Well, I know there's one-- Bert took me." "You know how annoying it is when the waiter puts his thumb in your food?" "This is worse." "Hey, Amy, you ready to go?" "Sure." "Let me just grab my purse." "I cannot believe you are going through with this." "You know I like this girl, and..." "Is that my blazer?" "I didn't come here to debate whose blazer I'm wearing." "It's mine." "I came here to teach you a lesson." "If you like a girl, go out with her." "If not, something bad could happen." "And it doesn't get much worse than this." "Hey." "Oh, where's Bert?" "Is he coming tonight?" "No, he's out with my assistant, Amy." "The one that you like but you're scared to ask out?" "I'm not scared, it's just unprofessional." "Anyway, she's doing an article on romantic places in Chicago, and Bert volunteered to go out with her." "Oh, dear." "Sucks for you." "Oh, he's going to get on that." "It's not a date, he's just doing it to teach me a lesson because he wants me to ask her out." "So, he's going to have sex with her?" "No, Mike, he's not." "Well, of course he is-- it's not much of a lesson if he doesn't have sex with her, is it, Andrew?" "Bert can't just decide a woman is going to have sex with him." "He's not Colin Firth." "What is your obsession with Colin Firth?" "I'm not obsessed, he's objectively handsome." "Oh, I think Bert's better-looking." "Oh, yeah, and Bert's the real deal." "If you think about it, Bert's probably the last person you want going out with a girl you like." "He is not going to sleep with her, okay?" "Okay." "Okay." "He's going to." "I don't see what makes this place so romantic." "All the waitresses have their shirts on." "You're funny." "Okay." "Excuse me." "Yes, Andrew, why are you bothering me on my date with your hot assistant?" "Did you perhaps grow some nuts?" "You made your point, you can go." "You ready to break your stupid rule?" "I don't have to; my rule is that I won't date my assistant." "So, here's my plan." "I mentor Amy, help her get a few more articles, and talk her up to the powers that be, and eventually get her promoted to writer." "Then, in six months, when she's no longer my assistant, boom, I suddenly swoop in and ask her out." "So... you can go." "Look, I'm your friend;" "I'm trying to help you out here." "But if I need to sleep with this girl to do that, I will." "Wait, wait, wait, wait." "What?" "Please don't?" "I got another call;" "I got to go." "Hello?" "Bert, it's Mike." "I understand you're probably on the verge of having sex with Andrew's assistant, but if you could just give me a moment." "Yeah, what do you need, Mike?" "Well, fantastic news for you." "Congratulations, you're my new go-to person!" "Yeah, I can't do that." "Aw, why not?" "I'm fully booked." "I'm already the go-to person for Andrew and my buddy Rollo, and a guy from my fantasy football league who likes Andrew." "Well, that's too bad, I guess." "Do you know anyone else who might be keen to..." "I got another call;" "I got to go." "Well, look at that, I do have another call." "Hello?" "Okay, Bert, I didn't want to have to do this." "This is your last chance to leave, or else." "Or else what?" "You'll shorten your mentor plan by three months?" "Check your phone." "My cigar." "What are you doing?" "Listen closely." "If you ever want to see your cigar again, you will follow my directions." "Tell Amy you had a great night, but you have to go." "Then leave a generous tip-- 18 percent is customary, 22 if the service is exemplary." "Then I want you to bid her goodnight and go home." "Face it, Bert, I have you by the cojibas." "I think you're bluffing." "You would never smoke a cigar in our apartment." "You're right." "But you forget we have a balcony." "Don't hang up, I'm on my way." "If you had just asked her out, this all could've been avoided." "I am not going to give up being a gentleman." "I think you hide behind this gentleman crap because you're afraid." "Afraid of what?" "Afraid of putting yourself out there." "Your stupid rules are preventing you from enjoying life." "Oh, yeah?" "Well, you are doing the same thing." "How dare you!" "Hold that thought, I'll be right up." "Keep the change." "Show me the cigar so I know it's safe." "All right, how do I do the same thing?" "You're not letting yourself enjoy this cigar because of your stupid rule about waiting for a special occasion." "But think about it." "You were all-state wrestling champ in high school." "You opened your own business." "You have accomplished a lot." "Now, stop making excuses and smoke the damn cigar." "Holy crap." "You're right." "I'm awesome." "Good for you." "And you know what?" "When I'm done with this cigar," "I'm gonna go back and try and bang your hot assistant." "You're not banging anyone." "I am." "And of course, by banging I mean politely asking out and hoping she says yes." "Amy." "There's something I have to tell you." "Can I get a water?" "Andrew, is everything okay?" "Bert rushed out of here so fast." "Is his friend Stogie all right?" "He's fine." "He's a cigar." "Okay..." "What are you doing here?" "I have to tell you something." "I have never met anyone as obsessed with grammar as I." "Well, I've never met anyone with whom" "I can harmonize as well as I can with you." "♪ You..." "♪ You..." "I like you, Andrew." "You do?" "Yeah, way better than my last boss." "That must have been... weird." "Yeah." "And I have this rule about not dating people I work with." "Course you do." "Although, sometimes, that rule is... kind of hard to stick to." "Yeah, I... get that." "But I think it's good to have rules, don't you?" "Yeah, I do." "Definitely, a big rules guy." "I love rules." "I mean, where would we be without rules?" "We'd be animals." "We should probably go." "Separate cabs?" "Yeah, absolutely." "What were the chances she'd have the same stupid rules you do?" "I know, and the irony is the fact that she has that rule makes me like her even more." "You know, it's like my uncle used to say." ""Love is like trying to fit a two-inch pipe adapter into a one-inch check valve."" "Is your uncle a plumber by any chance?" "Yeah, how'd you know?" "Lucky guess." "Well, at least you put yourself out there." "And you got to smoke your cigar." "How was it, by the way?" "Awful." "I should've smoked that thing when I was eight."