4 Things You Need to Know to Succeed at Online Sugar Daddy Dating4 Things You Need to Know to Succeed at Online Sugar Daddy Dating

If you’re one of the many younger women looking for older men to date, have you ever thought about going online to find a sugar daddy? An increasing number of sugar daddies are joining dating web sites in hopes of finding beautiful young women to
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The Best Way to Strengthen Your May-December RelationshipThe Best Way to Strengthen Your May-December Relationship

When you’ve been in a May-December relationship with the same person for a long time, it can sometimes start to feel like it’s fizzling out. That’s not to say that the relationship has gone completely sour—it’s just not as exciting as it may have been
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Scientific Proof That Sugar Daddy Relationships Really Do WorkScientific Proof That Sugar Daddy Relationships Really Do Work

Even though sugar daddy dating has gotten more popular in recent years, a lot of people still have doubts about the legitimacy of having a sugar daddy—many people assume that it can’t possibly be a healthy relationship if it’s based on money. But the results
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This Is What Older Men Are Really Looking For in a Sugar BabyThis Is What Older Men Are Really Looking For in a Sugar Baby

What's the first thing you notice about a man when you’re looking for a sugar daddy? If you’ve been in age gap relationships with older men before, do you remember what it was about them that attracted you so much? It turns out that a
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Insights From a Real-Life Sugar DaddyInsights From a Real-Life Sugar Daddy

Sugar daddies usually get a bad rap for their lifestyle—spoiling beautiful, young women with money and expensive gifts isn’t exactly everyone’s idea of a healthy relationship. But one real-life sugar daddy, Alan Schneider, wants the world to know that there’s nothing wrong with today’s women
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What Your Online Dating Profile Is Really Saying About YouWhat Your Online Dating Profile Is Really Saying About You

If you’re looking for a sugar daddy, dating sites are always a good option, especially one that's specially designed to match rich, older men with beautiful younger women. Sugar daddy dating sites are a great way to meet older men that you may otherwise have
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Why More Single Moms Are Looking For a Sugar DaddyWhy More Single Moms Are Looking For a Sugar Daddy

There have been several surveys showing that many female college and university students are turning to the sugar daddy lifestyle to cover costs. But there’s another group of women who are cashing in on the financial perks of having a sugar daddy: single moms. According to
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Can This Unusual Arrangement Improve Your May-December Relationship?Can This Unusual Arrangement Improve Your May-December Relationship?

Relationships aren’t easy, especially a May-December relationship. Dating an older man isn’t always just about the money—they require just as much, if not more, effort than regular relationships. Women who date older men are more likely to face issues about kids, marriage, and sex, which
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Do This If You Want a Hotter Sex Life with Your Sugar Daddy

All relationships will inevitably have their ups and downs, and age gap relationships are no different. In fact, the age difference can sometimes feel like it’s pulling you apart. But that’s why it’s especially important in age gap relationships to find a common ground. Rather
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What Happened When My Hot Older Boss Caught Me Reading a Naughty Book at Work (Not What I Expected): Part 2What Happened When My Hot Older Boss Caught Me Reading a Naughty Book at Work (Not What I Expected): Part 2

“Oh, I’m sorry! What are you reading there?” Brandon asked as he motioned to the paperwork I had put my book under. I was mortified, but I tried my best to hide it. “Uh, just a book you know, just to pass the time.” I waved
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How Do I Stop My Ex-Husband From Introducing Our Kids to His New Sugar Baby?

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QUESTION: My ex-husband has just started dating a much younger woman. He’s got our two kids for the holidays, and I’m nervous that he’s going to introduce them. She seems nice enough from what he’s told me, but I don’t know if I’m ready for that. How do I draw the boundaries?
CHELSEA SAYS: This is a tricky one, because things always get more complicated when there are kids involved. The good thing is it sounds like you and your ex-husband are on pretty good terms if he’s told you all about his new younger woman.…

4 Ways to Land a Rich, Sexy Older Man…And Keep Him: Part 1

4 Ways to Land a Rich, Sexy Older Man…And Keep Him: Part 1When I first met my older gentleman, I was extremely intimidated. He was a powerful man with a very strong character, but he also had a great personality. I’m not very outgoing, so I often come across as very shy at first. I still managed to land myself a great guy.
If you’re shy like me, you can actually use this to your advantage. When you’re first potentially looking for an older man or sugar daddy, always keep in mind that you don’t want to come across as being too forward. You don’t want to put it right out there that you’re on the market for an older man with money—you’ll just end up looking like a gold digger who’s only interested in his money.…

A Surprising New Place to Meet a Future Sugar Daddy

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If you’re on the hunt for a sugar daddy, you know it isn’t always as easy as walking into a bar, cuddling up to a handsome older man, and calling it a night. It usually takes just a little more effort to find a sugar daddy worth keeping, but it helps if you know where to look. The next time you’re invited to a wedding, you should join in the festivities because, as a new survey reveals, there’s a good chance you could meet someone. If you’re a younger woman on the hunt for a sugar daddy, weddings are a good place to start looking.…

The Outrageous Gift My Sugar Daddy Gave Me to Make Up For My Horrible Boyfriend: Part 1

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For days, I was in turmoil over breaking up with my boyfriend, Kirk. It’s funny, when everything was fine between Kirk and me, I was happy with my sugar daddy, Keith. But now it seemed like I didn’t want to be happy unless they were both in my life. Kirk couldn’t deal with knowing about my relationship with Keith, and that constantly led to arguments. And, because Kirk couldn’t handle the fights, he would just disappear.
After I decided to leave Kirk, he called consistently and kept asking people to speak some sense into me.…

IN THE NEWS: Michael Jordan marries Yvette Prieto, 15 Years Age Difference,

149137726If at first you don’t succeed, marry a much younger model.
On Saturday, April 27, 2013, 50-year-old basketball legend Michael Jordan and former Cuban-born model Yvette Prieto, 15 years his junior, married in Palm Beach, Florida, in front of a few hundred of their closest friends and family. The six-time NBA star and Prieto got engaged in 2011 after dating for three years.
Without question, the greatest basketball player of all time, Jordan helped popularize the NBA beyond its American borders throughout the 1980s and 1990s.…

Being Stabbed in the Back By My Best Friend Because of My Older Man

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I feel like you’re sleeping with my father; it’s just weird,” she said when I revealed the age of my older man. After years as friends, she never minced words. We had spent our college years together dancing, drinking and flirting with guys our own age and we were also, as the cliché goes, like sisters. 
I anticipated her skepticism when I told her I was dating someone 25 years older than me, but I was confident she would get over it. Not only did she help us plan our wedding, but over the course of five years, I could tell she had grown to like him; or so I thought.…

He’s a Liar, a Cheater, and Filthy Rich…Here’s How to Make Him Pay: Part 1

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Once I broke off the engagement with my older man, Derrick, I saw a completely different side of him. He became much more distant, and we went more days than ever before without seeing each other. I still had my car, house, handbags, clothes, and jewelry—all the gifts he had given me while we were together. In fact, now that he was being more distant, he actually bought me even more stuff.
As nice as it was, it just wasn’t worth it for me anymore. I was slowly falling out of love with Derrick.…

How to Talk to Your Rich Older Man About Your Sex Life (Or Lack Thereof): Part 1

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Each time I went to see my new sugar daddy Michael it was never for more than an hour or two. Each time he gifted me some combination of jewelry, money, and most importantly, attention. The attention I got from Michael was intoxicating; just as my friend (and his ex) Kate had said it would be.
All in all, he maintained gifts of money in the $3,000 range at minimum. I usually saw him two or three times a week, sometimes at midnight, otherwise around 2 or 3 o’clock in the morning. That was our unspoken arrangement, just as it was for Kate and surely many others before and after me.…

The Big Family Secret That Ruined My Chances of Marrying a Rich Older Man

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My older fiancé, Patrick, had three kids, and out of all of them, it was Michael I saw the most. Because he worked so closely with his father at the family business and lived downtown, his dad frequently wanted to socialize with him after work, usually at a sports bar. Patrick always wanted me there, too, so I frequently joined them. His son was no longer rude to me, like he was the first time we met. He tolerated me, and out of respect for his father, he treated me like a lady.
We would hang out with him for an hour or two and then leave him to be with his friends.…

What My Sugar Daddy Did to Make Me Want to Leave Him and All His Money: Part 1

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As the cruise came to an end, my sugar daddy, Marco, held me closely as if to say he was sorry for our fight, but without ever actually saying that he was sorry for yelling at me about bringing up the topic of marriage. Marco was in control; it was his way or the highway and he’s only ever apologized once during our entire time together. That’s just the way it was, but I didn’t know any better at the time.
After the cruise docked, I asked for some space from Marco while I walked the streets of downtown Seattle for hours.…

How Do I Take My Sugar Daddy/Sugar Baby Relationship to the Next Level?

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QUESTION: I met this older guy at a bar and we hit it off right away. We went on a few dates and there was a lot of great chemistry—there still is. He’s in his mid 40s and had spent most of his life building his business. So, now that he has the money to sit back and enjoy life, he says he just wants to have fun. I never thought of myself as a sugar baby, but that’s kind of where the relationship went, and I was fine with that because that’s what I thought I wanted too. But it’s been a couple months now, and, even though I love having him as my sugar daddy, I’ve realized that I want more out of this relationship.…

Why The Sex Is So Much Better with a Man Almost Twice My Age

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Let’s talk about my sex life with my older man. Sam was 46 and I was 24. By the time we got together, he had years of sexual experience “under his belt,” with his marriage, with extramarital affairs, and with using his creative mind and spirit.
My young husband and I had never ventured outside of traditional intercourse. We were both shy and inexperienced, and I guess we just didn’t desire to venture into those waters. So imagine my first experience of it with Sam. Wow! Where had THIS been all my life?…

How I Made My Millionaire Boyfriend Want to Marry Me: Part 1

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So, it began. My older man Marco flew out early Monday morning and I started my new job as a strip club bartender that night. I trained four nights that week and made less than half of what the dancers admitted to making, but more than what I made working full-time for two weeks at the grocery store. That was good enough for me, although between school, my work, and Marco’s travel, the house was empty and lonely. So, after some coaxing, Marco and I got a dog, a big dog. He weighed more than me, but was great for me while Marco was away.…

Sex with My Older Man Isn’t as Hot as It Used to Be—What Happened?

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QUESTION: I’m 34 and my boyfriend is 59. We’ve been together for about seven years now, and at first, the sex was amazing. We couldn’t get enough of each other. But now, it’s different. He doesn’t seem as interested anymore and I’m not sure if it’s me, another woman, or if it’s impotence starting to creep into our sex life. What do I do?
CHELSEA SAYS: Just because you’re not having sex as often as you used to, it doesn’t mean he’s having an affair. If he is cheating, there will be other signs, like sneaking off to answer a phone call, never leaving his phone unattended, all of a sudden having to work late and take business trips, and suddenly spending more time on his appearance.…

The Epic Disaster I Made of My Chances at a Life with a Rich Older Man: Part 1

The Epic Disaster I Made of My Chances at a Life with a Rich Older Man

I had just had an abortion because I didn’t know if the baby was my husband, Robert’s, or my lover, Derrick’s. And after having gone through the traumatic procedure, here I was, standing at Derrick’s door, ready to end our May-December relationship once and for all.
When Derrick opened the door, the look on his face was shock. I must have looked like hell. He grabbed my hand and walked me to the living room. Then he gave me tissues and brought me a glass of water with lemon. I took a sip and set it down.…

Should I Get My New Sugar Daddy a Christmas Gift?

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QUESTION: With the holidays around the corner, I’m left wondering whether I should give my sugar daddy a Christmas gift. We haven’t been in a relationship for a long time (about two months) and, being married with kids, I don’t think that we’ll get much time to plan something special together. Do I get him something? If yes, what? I realize that I could plan a little something special, but not having been together long, everything is still special. Help!
CHELSEA SAYS: This is always a tough question with sugar daddy relationships, especially when they’re new.…

What I Did to the Sugar Baby Who Tried to Earn the Necklace From My Sugar Daddy Before Me: Part 1

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Mrs. Roberts had just told me that she used to be Mr. Brown’s lover before I was in the picture. As upset as I should have been, I was just angry. I got up out of my seat and walked over to Mrs. Roberts. I looked her right in the eye and told her that I really didn’t care about the affair that she and Mr. Brown had in the past. He was with me now and that was how it was going to be. There was nothing she could say to scare me away.
Mrs. Roberts, without so much as even flinching, told me that she could destroy me, and that she had the power to ruin my career.…

Why It’s Always a Good Idea to Flirt with a Hot, Rich, Older Man at Work: Part 1

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I had just left my sleazebag boyfriend and had moved back home. To try and get my life together again, I decided to get a retail job in the mall until I could re-enroll in school again. My hours were very limited at the new job. And since it was seasonal, I did my best to make sure I was being noticed so that it would hopefully lead to a permanent part-time position. I slaved away at the register, did as many closing shifts as I could, and even covered shifts for half of the girls that were newly hired with me.…

The X-Rated Trip My New Sugar Daddy Planned for Our Second Date: Part 2

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As usual, the Greek God’s secretary phoned me not too long after I spoke with the Greek God. She said that I would be going back to Las Vegas and if I wanted to take Tori along, she would make the flight and room reservations. I couldn’t wait to give her a call to invite her for yet another fun weekend. Tori accepted the invitation and my Greek God was waiting at the suite when we arrived. He always made sure we were in the nicest suites that Las Vegas had to offer.
The moment we looked at each other, our eyes locked.…

How an Expensive Gift Made Me Feel Better About Settling For a Much Older Man: Part 2

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The best part of this trip with the Stetson man was that we extended it through the weekend. He made the whole weekend all about me; the world was my oyster. On our first free day, he rented a limousine to drive us to Atlantic City. My heart warmed remembering the weekend. I had purchased a magazine for the drive that contained a quiz pertaining to marriage and compatibility. I had persuaded him to take the quiz with me. We both answered the questions; we laughed and teased each other about our answers, and finally agreed that we would survive marriage, except marriage was never an option for us because, even to this day, his divorce isn’t final.…