“You're Fired. Now, Would You Like to Have Dinner With Me?”

SILVER & SAPPHIRE MAGAZINE Love Younger. Live Larger. THE DIRECT APPROACH — JUST ASK! Some women wait for romance. Others make it happen. In this recurring Silver & Sapphire feature, successful, wealthy women over 50 share how one remarkably direct question to a beautiful younger woman led to an unexpected night, an extraordinary offer, and sometimes a completely new life together. This Issue: Vanessa, 53 & Emily, 29 A hotel empire worth millions. A young employee dismissed for refusing a wealthy guest's advances. One furious businesswoman who decides to intervene. And a proposition that turns the worst evening of Emily's life into something neither woman could possibly have imagined. HER STORY — VANESSA, 53 At fifty-three, Vanessa Whitmore was beautiful, extraordinarily wealthy, twice divorced, and quite possibly the most intimidating woman in the American luxury hotel industry. She owned fourteen luxury hotels, maintained residences in Miami, New York, and Los Angeles, and had accumulated a personal fortune estimated at $145 million. Her employees described her as demanding but fair, although several admitted that her unexpected visits could reduce experienced hotel managers to nervous wrecks. Vanessa considered that a useful professional accomplishment. "I built my company from one struggling boutique hotel," she told us. "I expect people to treat our guests beautifully, our employees fairly, and our money responsibly. Apparently those are very demanding expectations." Her romantic life was considerably less successful. She had been married twice, first to a man who had found her ambition inconvenient, then to a woman who had found her money considerably more interesting than her personality. Her second divorce had been finalized two years earlier. Since then, Vanessa had dated occasionally, but she had become increasingly impatient with elaborate courtship rituals. "I wanted a beautiful younger girlfriend," she explained. "Someone affectionate, intelligent, adventurous, and capable of making me laugh. I didn't want another business associate pretending to be romantically interested in me." She paused. "And I certainly didn't want another woman who considered my bank account my most attractive feature." At fifty-three, Vanessa had no intention of becoming conservative, retiring from business, or apologizing for the fact that she preferred younger women. She dressed magnificently, favored short designer skirts, expensive jewelry, and spectacular heels, and had recently purchased a bright red sports car that her accountant considered an unnecessary extravagance. "I told him the accountant was an unnecessary extravagance too. That ended the discussion." HER STORY — EMILY, 29 Emily Carter had once been a promising young hotel-management graduate with dreams of managing a luxury resort. At twenty-four, she married a charming businessman named Jason, who persuaded her to leave her first management position and help him establish a restaurant. For three years, Emily worked twelve-hour days, handled the staff, managed the accounts, and developed a successful catering business. Then she discovered that Jason had been having an affair with their restaurant's hostess. When she confronted him, he told her that the business was entirely in his name and that she had no legal claim to its profits. The ensuing divorce consumed her savings. Worse still, Jason accused Emily of financial misconduct, allegations that were eventually withdrawn but nevertheless damaged her professional reputation. She struggled to find another management position. Then her mother was diagnosed with an aggressive illness. Emily spent nearly everything she had left helping with medical and household expenses, eventually moving back into her childhood home to provide care. Her mother died eight months later. "My mother was the last person who believed I could still have a wonderful life," Emily told us. "When she died, I felt as though the last good part of my world had disappeared." Emily inherited the modest family home, but outstanding debts forced her to sell it. At twenty-nine, she was divorced, unemployed, deeply in debt, and living in a tiny rented room. Eventually, she accepted a position as a guest-services assistant at one of Vanessa Whitmore's luxury hotels. The job paid considerably less than her former management position, but Emily was grateful to be working. Until the evening she met Vanessa. THE INCIDENT — THE WRONG MAN TO REFUSE S&S: Emily, what happened that evening? Emily: "I was assigned to assist a very wealthy hotel guest who had booked our presidential suite for an entire week. He was a regular customer, extremely demanding, and apparently accustomed to getting whatever he wanted." S&S: Including attention from female employees? Emily: "Unfortunately, yes. He'd been making inappropriate comments for two days. That evening, he asked whether I'd like to join him upstairs for a private drink after my shift." S&S: What did you say? Emily: "I declined politely." Vanessa: "As she had every right to do." Emily: "He became angry. He told me that women like me ought to be grateful when successful men showed them attention." S&S: And then? Emily: "He complained to my supervisor, claiming I'd insulted him and deliberately embarrassed him in front of other guests." S&S: Was that true? Emily: "Absolutely not." Vanessa: "The security footage subsequently confirmed that." Emily: "But my manager didn't want to lose an important customer. He called me into his office and told me my employment was being terminated." S&S: Immediately? Emily: "Yes. He told me to collect my belongings and leave through the employee entrance." S&S: That must have been devastating. Emily: "I had eighty-six dollars in my bank account. My rent was due in four days. I couldn't believe it was happening again." THE ENCOUNTER — JUST ASK! S&S: Vanessa, how did you become involved? Vanessa: "I happened to be visiting the hotel unexpectedly. I was walking through the lobby when I noticed a young woman crying near the staff elevators." Emily: "I was trying to pull myself together before leaving." Vanessa: "I asked whether she was all right." Emily: "I told her I'd just been fired." Vanessa: "Then I asked why." Emily: "I explained what had happened, although I didn't know who she was." S&S: You didn't recognize the owner of the hotel? Emily: "I'd seen photographs of her, but she looked completely different in person. She was stunning — dark shoulder-length hair, a beautiful purple designer outfit, diamonds, and the most incredible heels." Vanessa: "I'm delighted somebody appreciates the effort." Emily: "She listened to my story, became very quiet, and asked me to accompany her to the manager's office." S&S: What happened there? Vanessa: "I introduced myself and asked the manager to explain why he'd dismissed an employee for refusing a guest's personal advances." Emily: "I thought he was going to faint." Vanessa: "He attempted to explain that the guest was extremely valuable to the hotel." S&S: And your response? Vanessa: "I told him that an employee's dignity was rather more valuable." Emily: "Then she asked him to arrange for the security recordings to be preserved and reviewed." Vanessa: "And I informed him that he was being relieved of his management duties pending an investigation." S&S: So Emily got her job back? Vanessa: "I offered to reinstate her immediately, with full back pay for the interrupted shift and a formal investigation into the incident." Emily: "I was completely overwhelmed. I kept thanking her." Vanessa: "And I kept telling her that she hadn't done anything wrong." S&S: And then came the outrageous question? Emily: "Oh, yes!" Vanessa: "I was looking at this lovely young woman, and suddenly I realized how attractive she was." Emily: "She asked whether I had plans that evening." S&S: What did you say? Emily: "I told her I was going home to cry, eat instant noodles, and worry about my rent." Vanessa: "Which sounded like a perfectly dreadful evening." Emily: "Then she said, 'Emily, you're no longer expected to work tonight, and I would very much like to take you to dinner.'" S&S: That seems fairly innocent. Emily: "It would have been, except she wasn't finished!" Vanessa: "I told her that because I owned the hotel, I could hardly pretend there wasn't an awkward professional situation. So I offered to arrange dinner somewhere entirely separate, with no expectations and no consequences for her employment if she declined." Emily: "Then I asked whether she was inviting me to dinner as an apology." Vanessa: "And I said, 'No, darling. I'm inviting you because I think you're absolutely gorgeous, and I'd like to kiss you before the evening is over.'" S&S: Good heavens! Emily: "I nearly dropped my handbag!" Vanessa: "She looked so astonished that I thought I'd made another terrible managerial decision." Emily: "I asked, 'Are you seriously asking me out?'" Vanessa: "I said, 'Entirely seriously. And if you're interested, I'd be delighted if dinner turned into breakfast tomorrow morning.'" S&S: What did you say? Emily: "I asked whether she was married." Vanessa: "No." Emily: "'Do you have a girlfriend?'" Vanessa: "No." Emily: "'And you're actually fifty-three?'" Vanessa: "Yes." Emily: "Then I said, 'Well, I'm twenty-nine, completely broke, and haven't been on a decent date in three years. Are you absolutely sure you know what you're getting yourself into?'" Vanessa: "I told her, 'Darling, I own fourteen hotels. I rather enjoy a challenge.'" Emily: "And I started laughing!" THE DATE — DINNER WITH THE BOSS S&S: Where did you go? Vanessa: "To a beautiful restaurant overlooking the ocean. I called ahead and arranged a private table." Emily: "She also had a car waiting outside. A beautiful black Rolls-Royce!" S&S: Were you nervous? Emily: "Terribly. I'd never been on a date with a woman before, let alone someone twenty-four years older who owned the hotel where I worked." Vanessa: "She spent the first twenty minutes apologizing for practically everything." Emily: "I was so intimidated!" Vanessa: "Which was ridiculous. I thought she was wonderful." They ordered dinner, talked about Emily's previous marriage and professional ambitions, and eventually moved to a secluded terrace overlooking the Pacific. Emily: "Vanessa asked what I'd wanted to do before everything went wrong." S&S: And? Emily: "I told her I'd dreamed of managing a luxury resort someday." Vanessa: "Which impressed me enormously. She clearly understood the hotel business." Emily: "Then I asked about her romantic life." S&S: What did she say? Vanessa: "I told her I'd been married twice, divorced twice, and had developed a rather unfortunate habit of falling for beautiful women who didn't necessarily appreciate me." Emily: "Then I said, 'Well, perhaps you've been choosing the wrong women.'" Vanessa: "And I asked whether she was volunteering to improve my judgment." Emily: "I said, 'Possibly.'" S&S: Who initiated the first kiss? Emily: "I did!" Vanessa: "Rather unexpectedly." Emily: "We were standing on the terrace, looking at the ocean, and I suddenly realized that I wanted to kiss her. So I asked." Vanessa: "And I told her I'd been waiting all evening." S&S: And the rest of the night? Emily: "Wonderful. We went back to Vanessa's private penthouse, talked for hours, and eventually spent the night together. She was affectionate, romantic, and incredibly considerate." Vanessa: "Emily reminded me what it felt like to be wanted for myself." Emily: "And Vanessa made me feel beautiful again." THE MORNING AFTER — AN IMPOSSIBLE OFFER S&S: Vanessa, apparently dinner wasn't the end of your extraordinary generosity? Vanessa: "Not remotely." Emily: "I woke up in this magnificent bedroom overlooking the ocean. Vanessa was sitting beside me wearing a silk robe, drinking coffee and reading the financial news." Vanessa: "Some habits are difficult to abandon." Emily: "She kissed me good morning and asked whether I'd slept well." S&S: And your answer? Emily: "I told her it was the happiest night I'd experienced in years." Vanessa: "Then I asked whether she'd like to repeat the experience." Emily: "I said yes immediately." Vanessa: "Then I asked whether she might enjoy spending an entire weekend together." Emily: "I said yes again." S&S: And then? Vanessa: "I told her I'd like to date her properly, if she was interested." Emily: "Then she asked the question that completely changed my life." S&S: Which was? Vanessa: "'Emily, how would you feel about becoming my girlfriend and eventually sharing my homes, my travels, and my life?'" Emily: "I thought she was joking!" Vanessa: "I assured her I was perfectly serious." Emily: "Then she said she'd like to help me return to hotel management." S&S: Through her company? Vanessa: "I suggested that Emily pursue a management training program, but at another hotel group, where she could develop independently and nobody would be concerned about our personal relationship." Emily: "That impressed me more than anything. She wasn't trying to make me dependent on her." Vanessa: "Then I told her I had a beautiful guest suite at my Miami residence, and she was welcome to stay temporarily while arranging her finances and housing, whether or not our relationship continued." Emily: "I started crying." Vanessa: "I told her there was absolutely no reason to rush into anything. I wanted us to spend time together and discover whether we could make each other happy." S&S: So what did you say? Emily: "I told her I couldn't promise forever after one night." Vanessa: "A very sensible answer." Emily: "But I could promise that I wanted to see her again." Vanessa: "Which was precisely what I wanted to hear." WHERE ARE THEY NOW? Twenty-one months later, Vanessa and Emily are still together. Emily completed an accelerated management training program with an independent international hotel company and now holds a senior guest-experience management position at a luxury resort in Miami. She initially stayed in Vanessa's guest suite, but according to Vanessa, the arrangement became rather unnecessary after six weeks. The couple now divide their time between Miami, New York, and Vanessa's beachfront property in California. Emily has become a familiar presence at Vanessa's charity events, and Vanessa occasionally attends hospitality-industry conferences alongside her younger girlfriend. Vanessa: "I thought I was rescuing an employee from an unfair dismissal. Instead, I discovered the woman I wanted to share my life with." Emily: "I thought I'd lost everything that evening. Instead, I found someone who believed in me before I could believe in myself again." S&S: And what happened to the manager who dismissed you? Emily: "He was eventually dismissed following the investigation." Vanessa: "Which was entirely unrelated to my romantic interest in Emily. His behavior had violated several company policies." S&S: Do you still joke about that first evening? Emily: "Constantly!" Vanessa: "She has a particularly irritating sense of humor." S&S: How so? Emily: "Whenever Vanessa gets too bossy, I look at her and say, 'Careful, darling. You already fired me once.'" Vanessa: "And I remind her that I wasn't the one who fired her." Emily: "Then I say, 'Well, perhaps you should make it up to me anyway.'" S&S: And does she? Vanessa: "Usually." Emily: "Always!" THE DIRECT APPROACH — JUST ASK! Another love story from Silver & Sapphire Magazine — where successful women discover that sometimes the shortest distance between loneliness and happiness is one simple question. Love Younger. Live Larger.