“How Much for the Whole Night?”

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: Helena, 52 & Samantha, 27 A freezing street corner at two in the morning. A terrified young woman wearing the shortest leopard-print skirt she owned and heels she could barely walk in. A black limousine that unexpectedly stopped. And five little words from a wealthy stranger that began the most extraordinary night of both women's lives. HER STORY — HELENA, 52 Helena Blackwood had spent twenty-seven years accumulating a fortune that most people could scarcely imagine. At fifty-two, she controlled a successful international logistics company, owned substantial interests in several luxury resorts, and maintained residences in Beverly Hills, Manhattan, and London. Her personal fortune exceeded $320 million. She was tall, strikingly beautiful, with shoulder-length dark brown hair, an elegant figure, impeccable taste in designer clothing, and a weakness for expensive heels that bordered on obsession. Her staff described her as demanding, intelligent, and extraordinarily generous when she believed someone deserved her help. Her romantic history was considerably less impressive. Helena had divorced her husband twelve years earlier after finally admitting that she had always been more attracted to women. Her first serious relationship with a woman lasted four years. Her second lasted eighteen months. Both ended after Helena discovered that the affection she believed she was receiving depended heavily upon her willingness to finance expensive lifestyles. "I was becoming rather cynical," Helena admitted. "Whenever a beautiful woman showed interest in me, I immediately wondered what she wanted." S&S: And did you still date? Helena: "Occasionally. But I had begun to suspect that being extraordinarily wealthy was actually a disadvantage when it came to finding genuine affection." S&S: Surely money has its advantages? Helena: "Oh, enormous advantages, darling. Beautiful houses, wonderful holidays, spectacular jewelry, and the ability to buy whatever takes your fancy. Unfortunately, you cannot order someone who genuinely loves you." For nearly two years, Helena had lived alone. Her closest companions were her longtime housekeeper, her personal assistant, and her chauffeur, Daniel, who had worked for her for fifteen years. She attended charity galas, entertained business associates, and occasionally took beautiful women to dinner. But she invariably returned to an empty bedroom. "I was fifty-two, wealthy beyond reason, and thoroughly tired of sleeping alone." Then, at two o'clock one cold November morning, Daniel slowed the limousine at a traffic light. And Helena noticed a young woman standing on the corner. HER STORY — SAMANTHA, 27 Samantha Reed had never imagined that she would become the kind of woman who stood on a street corner in the middle of the night hoping that a stranger might stop. She had grown up in a modest but loving family in Sacramento. Her father was an electrician, her mother worked as a nursing assistant, and Samantha had been the first person in her family to graduate from college. At twenty-three, she accepted a position as an administrative coordinator at a successful medical equipment company. She was beautiful, cheerful, hardworking, and engaged to a man she had loved since high school. Then her father died unexpectedly. Six months later, her mother suffered a disabling stroke. Samantha used her savings to help care for her, eventually reducing her working hours and abandoning plans to marry. Her fiancé grew increasingly resentful. One evening, he told her that he had fallen in love with someone else. Samantha returned his engagement ring. Three weeks later, she discovered that he had been using her credit cards to finance expenses she knew nothing about. The debts were enormous. She hired an attorney, but resolving the financial problems was painfully slow and expensive. Then her mother died. "I remember standing in the cemetery thinking that I'd lost every person who had ever really loved me," Samantha told us. She moved to Los Angeles, hoping for a fresh beginning, but her new job disappeared when the company announced major layoffs. She found temporary work, then lost that too. Her savings vanished. Her credit was ruined. Eventually, she couldn't pay her rent. She sold her furniture, most of her clothes, and nearly everything else she owned. A friend allowed her to sleep on a sofa for several weeks, but the arrangement ended when the friend's boyfriend moved in. Samantha spent three nights in her aging car. Then the car was repossessed. "I had eighty-three dollars, a small suitcase, and nowhere to sleep," she recalled. "I was twenty-seven years old, and I couldn't think of a single person I could call." On the evening everything changed, Samantha spent her last twelve dollars on food and a bus ride into an unfamiliar part of the city. She had noticed women standing along certain streets after midnight. Men occasionally stopped their cars. Money changed hands. Samantha had never done anything like that. She didn't know how to approach anyone, what to charge, what might happen afterward, or how to protect herself. But she was desperate. That evening, she opened her little suitcase and selected the shortest skirt she owned. It was leopard-print, barely reaching the middle of her thighs, a remnant from happier days when she and her girlfriends had enjoyed dressing up for nights out. She paired it with a tight black top and the highest heels she possessed, inexpensive black stilettos she'd bought years earlier for a nightclub party. She applied makeup in the restroom of a twenty-four-hour diner. Then she stood in front of the mirror and began to cry. "I looked ridiculous," she admitted. "I was freezing, the shoes hurt, and I didn't have the slightest idea what I was doing." At approximately 1:40 a.m., Samantha walked to a street corner and waited. She watched cars pass. She watched other women disappear into vehicles. She tried to imitate their confidence. But whenever a car slowed, she became frightened. Twice she nearly ran away. Then a magnificent black limousine approached. THE ENCOUNTER — FIVE WORDS THAT CHANGED EVERYTHING S&S: Samantha, what do you remember about that street corner? Samantha: "The cold. More than anything else, I remember being terribly cold." S&S: What were you wearing? Samantha: "The shortest leopard-print skirt I'd ever owned, a tight black top, and ridiculously high black heels. I thought that was what women were supposed to wear." Helena: "She looked absolutely frozen." Samantha: "I was! My legs were shaking so badly I could barely stand." S&S: Had anyone approached you? Samantha: "Two cars had slowed down, but I panicked both times. One driver shouted something unpleasant when I wouldn't approach his window." S&S: And then the limousine appeared? Samantha: "Yes. This enormous black car slowed down, and I thought the driver was probably looking for directions." Helena: "I was returning from a charity dinner. Daniel was driving, and I happened to notice Samantha standing alone." S&S: What caught your attention? Helena: "She was extraordinarily beautiful, but something wasn't right. She looked terrified rather than inviting." Samantha: "I was trying desperately to look as though I knew what I was doing." Helena: "She wasn't particularly successful." Samantha: "Thank goodness!" S&S: What did you tell your driver? Helena: "First I asked him to slow down. Then I asked him to stop." S&S: And then? Helena: "I lowered the window." Samantha: "I looked inside and almost fainted. There was this magnificent older woman wearing a short black designer dress, spectacular jewelry, and beautiful heels. I thought she must be a movie star." S&S: Did she introduce herself? Samantha: "No!" Helena: "I was rather direct." Samantha: "Rather direct? That's the understatement of the century!" S&S: What did you say, Helena? Helena: "I asked, 'How much for the whole night?'" S&S: Just like that? Samantha: "Just like that! I nearly fell off the curb!" Helena: "She looked so shocked that I immediately suspected she had no experience whatsoever." S&S: What did you answer, Samantha? Samantha: "I had absolutely no idea what to say. I didn't know what anyone charged for anything!" S&S: So what did you say? Samantha: "I sort of whispered, 'A hundred dollars?'" Helena: "I stared at her." Samantha: "She didn't answer immediately, and I thought I'd asked far too much!" S&S: What did you do? Samantha: "I panicked! I said, 'Fifty? Would fifty dollars be all right?'" Helena: "I couldn't believe what I was hearing." Samantha: "I thought she was going to drive away. I was standing there freezing, my feet were killing me, and I was about to lose the only chance I'd had all night." S&S: Did you lower your price again? Samantha: "I was about to! But then she opened the door." Helena: "I looked at her and said, 'Get in.'" Samantha: "And I practically jumped into that limousine!" S&S: What happened next? Samantha: "I sat down very carefully because I'd never been inside a car that expensive. The leather was beautiful, there were little lights in the ceiling, and I was terrified I'd get something dirty." Helena: "She was shaking from the cold." Samantha: "Then Helena said something to her chauffeur." S&S: What was that? Helena: "I asked Daniel to give her a hundred dollars." Samantha: "He opened his wallet, took out a hundred-dollar bill, and handed it to me. Just like that!" S&S: And your reaction? Samantha: "I stared at the money. I couldn't believe it. A hundred dollars was more than I had left in the entire world." Helena: "She looked utterly bewildered." Samantha: "I didn't know what I was supposed to do! Nobody had explained anything to me. I'd never done anything like this before." S&S: So what did you do? Samantha: "I put the money in my handbag, took a deep breath, and started unfastening my top." Helena: "I nearly jumped out of my seat!" S&S: Good heavens! Samantha: "I thought that was what she expected! She'd asked for the whole night, she'd paid me, and I assumed I was supposed to start immediately!" Helena: "I caught her hand and said, 'Good Lord, darling, what are you doing?'" Samantha: "I said, 'I'm sorry! Am I doing it wrong?'" Helena: "I told her to leave her clothes alone." Samantha: "Then I asked whether she wanted me to take my shoes off first!" Helena: "At that point I genuinely didn't know whether to laugh or cry." S&S: What did you say to her? Helena: "I said, 'Samantha, listen to me carefully. You don't have to take anything off, and you don't have to do anything for that money.'" Samantha: "I thought she'd changed her mind." Helena: "I explained that the money was hers to keep and that I wanted to get her somewhere warm and safe." Samantha: "Then I asked whether she still wanted me for the whole night." Helena: "And I told her, 'Yes, darling. I'd very much like you to come home with me, but you're going to have a hot meal, a shower, and a comfortable bed of your own.'" S&S: How did Samantha respond? Samantha: "I asked whether she was serious." Helena: "I assured her I was." Samantha: "Then I looked down at that hundred-dollar bill sticking out of my handbag and asked, 'But what am I supposed to do for the money?'" Helena: "I said, 'For heaven's sake, darling, nothing! Put it away before you lose it.'" Samantha: "And that's when I started crying." S&S: Why? Samantha: "Because I suddenly realized that I'd been standing on that corner, terrified of what a stranger might demand from me, and this beautiful woman had just given me more money than I'd hoped to earn without asking me to do anything at all." Helena: "I took off my cashmere coat and wrapped it around her." Samantha: "Then she asked Daniel to turn up the heating." Helena: "And finally I told him to take us home." S&S: Samantha, what were you thinking as the limousine pulled away? Samantha: "That I must have misunderstood something. Nobody had ever handed me a hundred dollars, wrapped me in an expensive coat, and told me I could have a comfortable bed without expecting something in return." Helena: "She kept looking at me as though she was waiting for the real conditions." Samantha: "I was!" Helena: "And I kept telling her there weren't any." Samantha: "I didn't really believe her until much later that night." THE LIMOUSINE — A VERY UNUSUAL NEGOTIATION S&S: Helena, did you know what Samantha was going through? Helena: "Not initially. But I realized very quickly that she wasn't accustomed to being approached like that." Samantha: "She asked how long I'd been working on that corner." Helena: "And she told me it was her first night." S&S: What did you think? Helena: "I thought I'd made a rather dreadful mistake." Samantha: "Then she asked why I was there." S&S: Did you tell her? Samantha: "Not everything. I was embarrassed. I told her I'd lost my job, my apartment, and my car, and that I needed money." Helena: "Then I asked where she was sleeping." Samantha: "I said I didn't know." Helena: "That was when I understood how desperate she was." S&S: What happened next? Helena: "I asked whether she'd eaten." Samantha: "I told her I'd had a sandwich that afternoon." Helena: "And I told Daniel to take us home." S&S: What did Samantha say? Samantha: "I asked what she wanted me to do when we arrived." Helena: "I told her she could have something to eat, take a hot shower, and get some sleep." Samantha: "Then I asked whether she was still expecting me to spend the night with her." Helena: "I told her she was welcome to stay in a guest bedroom, and that she didn't owe me anything." Samantha: "I couldn't believe it." S&S: Did you believe her? Samantha: "Not completely. I'd spent months discovering that almost everything in life came with conditions." Helena: "Which was precisely why I wanted her to have an evening without any." THE FIRST NIGHT — THE $100 QUESTION S&S: Samantha, what was your first impression of Helena's home? Samantha: "I thought we'd driven into a palace." Helena: "She's exaggerating." Samantha: "I'm not! There were enormous gates, fountains, gardens, marble staircases, chandeliers, and a driveway longer than the street where I'd been standing!" S&S: What happened when you entered? Samantha: "Helena introduced me to her housekeeper, Margaret, and asked her to prepare one of the guest bedrooms." Helena: "Then I asked whether Samantha wanted something to eat." Samantha: "I was starving." S&S: What did you have? Samantha: "Scrambled eggs, toast, fresh fruit, and the most wonderful hot chocolate." Helena: "She ate as though she hadn't had a proper meal in days." Samantha: "I hadn't." S&S: And then? Samantha: "Helena showed me a beautiful guest suite. The bathroom was bigger than my last apartment's bedroom." Helena: "Margaret had put out fresh towels, a robe, slippers, and some toiletries." Samantha: "Then Helena wished me goodnight." S&S: Was that all? Samantha: "I stopped her at the door." Helena: "She looked extremely nervous." S&S: What did you say? Samantha: "I asked, 'Helena, aren't you going to want your hundred dollars' worth?'" Helena: "I nearly choked." S&S: How did you answer? Helena: "I told her, 'Darling, I'm not going to ask you to earn a bed for the night. You're safe here. Please get some sleep.'" Samantha: "And I started crying again." Helena: "She'd had a very difficult evening." Samantha: "Then I did something unexpected." S&S: What? Samantha: "I hugged her." Helena: "A very enthusiastic hug." Samantha: "I told her nobody had been kind to me in such a long time." Helena: "Then I kissed her forehead, wished her goodnight, and left her to rest." S&S: So nothing romantic happened that night? Samantha: "No. And now I understand why that mattered." Helena: "I wasn't going to turn a desperate young woman's need for shelter into an obligation." Samantha: "But I went to bed thinking that Helena was the most beautiful woman I'd ever met." THE MORNING AFTER — THE IMPOSSIBLE OFFER S&S: Samantha, how did you wake up? Samantha: "At almost eleven! I hadn't slept that long in months." S&S: Where was Helena? Samantha: "She arrived a few minutes later wearing a gorgeous cream silk robe and fluffy high-heel slippers, carrying a breakfast tray." Helena: "I thought she deserved breakfast in bed." Samantha: "I nearly cried again!" S&S: What was on the tray? Samantha: "Coffee, orange juice, fruit, croissants, eggs, and a little vase of white roses." Helena: "Margaret had rather outdone herself." Samantha: "Then Helena asked whether I'd slept well." S&S: And your answer? Samantha: "I told her I'd never felt so safe in my life." Helena: "Then I asked whether she had anywhere to go." Samantha: "I said no." Helena: "So I made her an offer." S&S: Which was? Helena: "I told her she could stay in the guest suite while we arranged something more permanent. I also offered to help her find appropriate legal and financial advice so she could begin resolving her debts." Samantha: "I thought she was joking." Helena: "I wasn't." S&S: And then? Samantha: "I asked why she was doing all this for me." Helena: "I told her that she'd been very brave to admit how desperate she was, and that I was fortunate enough to be in a position to help." Samantha: "Then I asked whether she found me attractive." S&S: Really? Samantha: "Yes!" Helena: "I told her she was beautiful." Samantha: "Then I asked whether she liked women." Helena: "And I said very much." S&S: What did you say next, Samantha? Samantha: "I asked whether she'd consider taking me to dinner sometime." Helena: "That was a surprise." Samantha: "I told her I didn't want another arrangement or another favor. I wanted to know whether we might actually like each other." Helena: "And I told her I'd be delighted." S&S: But you didn't start a relationship immediately? Helena: "No. Samantha needed time to recover and regain some independence. I wanted her to be able to make decisions without feeling she owed me anything." Samantha: "Which made me fall for her even more." THE SECOND INVITATION — THIS TIME FOR FREE Two weeks later, Samantha had settled into Helena's guest suite, begun receiving help with her financial problems, and secured an interview for an administrative position with a company unconnected to Helena's businesses. She had also spent many evenings talking with Helena over dinner. They discovered a shared love of old films, Italian food, and long conversations that continued well past midnight. Then one Friday evening, Samantha appeared in Helena's sitting room wearing a beautiful blue cocktail dress and a pair of elegant heels. S&S: Samantha, what happened? Samantha: "I found Helena reading in the sitting room and asked whether she had plans that evening." Helena: "She looked absolutely gorgeous." Samantha: "Then I asked whether she'd take me to dinner." Helena: "I agreed immediately." S&S: Was it your first actual date? Samantha: "Yes. We'd spent plenty of time together, but this was the first time we'd both acknowledged that it was a date." They dined at a beautiful restaurant overlooking the Pacific and returned to Helena's mansion shortly before midnight. S&S: Who made the first romantic move? Samantha: "I did!" Helena: "She was becoming remarkably confident." Samantha: "I looked at Helena and said, 'Do you remember what you asked me the night we met?'" Helena: "I told her I would never forget it." Samantha: "Then I asked whether she still wanted me to spend the night with her." S&S: Oh my! Helena: "I asked whether she was absolutely certain." Samantha: "And I said, 'Darling, this time I'm asking because I want to. And just so we're clear, there's no hundred-dollar charge.'" Helena: "I laughed so hard I almost spilled my champagne." S&S: And did you spend the night together? Samantha: "Yes. It was wonderful. Helena was affectionate, romantic, and made me feel genuinely beautiful." Helena: "And Samantha made me feel desired in a way I hadn't experienced for years." THE SECOND MORNING AFTER — THE REAL PROPOSITION S&S: Helena, apparently the following morning you made the most extraordinary offer of all? Helena: "I did." Samantha: "I woke up beside her and found her watching me with this wonderful smile." Helena: "I asked whether she'd enjoyed our evening." Samantha: "I told her it was the happiest night of my life." Helena: "Then I asked whether she'd like to do it again." Samantha: "I said yes." Helena: "Then I asked whether she'd like to spend the following weekend with me in Santa Barbara." Samantha: "I said yes again." Helena: "Then I asked whether she'd consider becoming my girlfriend." Samantha: "I nearly fell out of bed!" S&S: After only two weeks? Samantha: "Exactly! I thought she couldn't possibly be serious." Helena: "I told her that I wasn't asking for an immediate commitment. I simply wanted to know whether she'd consider building something meaningful together." Samantha: "Then she said something I will never forget." S&S: What was that? Helena: "'Samantha, I have spent years wondering whether anyone could love me without wanting my money. You spent your first night here worrying that you had to give me something in exchange for kindness. Perhaps we've both been asking the wrong questions.'" Samantha: "I started crying." Helena: "And then I asked whether she'd like to find out what a real relationship between us might become." S&S: And your answer? Samantha: "I said yes. Then I kissed her." Helena: "A very enthusiastic kiss." Samantha: "And then I asked whether she was planning to charge me three hundred and twenty million dollars for the privilege." Helena: "I told her I might be persuaded to accept breakfast instead." WHERE ARE THEY NOW? Eighteen months later, Helena and Samantha are still together. Samantha completed a professional development program and now works as an administrative manager for an independent healthcare services company. She initially remained in Helena's guest suite but moved into the master bedroom several months after they began dating. The couple divide their time between Beverly Hills, Manhattan, and occasional extended holidays in Europe. Samantha has rebuilt her credit, accumulated her own savings, and begun volunteering with an organization that assists women facing housing insecurity. Helena says the mansion has finally become a home rather than an expensive place to sleep. And the famous leopard-print skirt? S&S: Samantha, whatever happened to that extraordinary outfit? Samantha: "Oh, I still have it!" Helena: "Unfortunately." S&S: Unfortunately? Helena: "She occasionally puts it on simply to embarrass me." Samantha: "The heels too!" Helena: "Ridiculous shoes." Samantha: "Which is rather amusing coming from a woman who owns several hundred pairs!" S&S: Do you ever joke about the hundred dollars? Samantha: "Constantly!" Helena: "She has an absolutely dreadful sense of humor." Samantha: "Last month Helena bought me a beautiful diamond necklace. I looked at the price and told her she'd apparently decided to pay for the next several thousand nights in advance." Helena: "I nearly choked on my champagne." S&S: One final question. Do you regret stopping that limousine, Helena? Helena: "Not for a moment. I thought I was rescuing a frightened young woman from a terrible night. Instead, I met someone who eventually taught me what genuine affection feels like." S&S: And Samantha? Samantha: "I stood on that corner believing my life was over. I had no idea what I was doing, what would happen, or whether I'd even survive the night. Then this beautiful woman stopped and asked the most outrageous question imaginable." S&S: And what would you say if she asked you again? Samantha: "I'd tell her the price has gone up." Helena: "Darling!" Samantha: "Now she has to love me forever!" Helena: "An outrageous demand." Samantha: "And your answer?" Helena: "Get in, darling." 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.