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How to Get the Truth Out of Your Man About His “Other Woman:” Part 1

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How to Get the Truth Out of Your Man About His “Other Woman”: Part 1Keegan had just given me the perfect birthday gift, and although he had spent the night and told me he loved me, I still had a feeling he wasn’t finished with dating other women. I had even asked him to be monogamous, but he never really gave me an answer. “I love you too,” I thought to myself. “But, honestly, where is this relationship even going?” Because Keegan was sending me some very confusing signals, I decided that I would figure out exactly what was going on. I logged into the dating web site, which I had helped him create the perfect profile for, and found that it had been active recently; he had been active on the site within the last two days!…

The post How to Get the Truth Out of Your Man About His “Other Woman:” Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.


How to Get the Truth Out of Your Man About His “Other Woman:” Part 2

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may december relationshipsKeegan dropped the big bombshell. “This other woman did manage to get me in bed with her, but I couldn’t get it up. She wasn’t who I wanted, and I am sorry.” He paused briefly before taking another step. “She started making threats. I was concerned she would try hurting herself or, even worse, hurting you. So I did what I thought was right, considering the situation. I wanted to let her down on a high note, and by that I mean I couldn’t just disappear or I firmly believed she would have hurt herself or someone else.…

The post How to Get the Truth Out of Your Man About His “Other Woman:” Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

4 Things You Need to Discuss with Your Older Man Before Things Get Serious

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age_gap_dating_may7_14Intimate relationships are never easy, especially in the early stages when you’re both trying to navigate through the rocky waters of getting to know each other. Sometimes the connection will spark immediately upon first contact, but other times, it needs a bit more work. As the early stages of your relationship progress, you should be able to determine if this is someone you can be with long-term. If you’re a younger woman dating an older man, it’s a given that the dynamics of your age-gap relationship will be a little different.…

The post 4 Things You Need to Discuss with Your Older Man Before Things Get Serious appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

How Sex with a Rich Older Man Landed Me in the ER (and Why I Didn’t Mind): Part 1

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may december relationshipsThere we were again—Keegan and I were back together and making love like rabbits. Things were finally back to normal; we were happy, together, exclusive, and finally on the same page about our relationship. His online dating profile was gone and his crazy stalker chick was out of the picture. So, we decided it was the perfect time for me to meet his friends. Would I pass their test? Would this hurt his career, or mine even? Only time would tell. As we got ready to head out and meet his friends, we decided it would be nice to have a little quickie before we left.…

The post How Sex with a Rich Older Man Landed Me in the ER (and Why I Didn’t Mind): Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

How Sex with a Rich Older Man Landed Me in the ER (and Why I Didn’t Mind): Part 2

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may december relationships“What if I can never give you the children you want?” I asked Keegan, scared and starting to cry. “You will, or I’ll trade you in for a newer model,” he said jokingly. He was always trying to make me laugh, especially at the most inappropriate times. It was his way of helping me to cope with things, to lighten the mood and make the situation at hand more manageable. The doctor did another scan just to confirm the location and twist before sending me back. Luckily, he found that the organ had already started turning and blood flow was starting to return naturally.…

The post How Sex with a Rich Older Man Landed Me in the ER (and Why I Didn’t Mind): Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The One Thing That Could Make You the Best He’s Ever Had in Bed

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may_december_relationships_may11_14If you’re dating an older man, chances are that you’ve been asked more than once about your sex life—is it as good as it is with a younger man? Can he keep up? If you’ve just started seeing your sugar daddy and things have progressed to the bedroom, it usually goes one of two ways: his experience will pay off, or it won’t quite match up. If sex with your older man just isn’t as good as you expected, it might be because there’s one important thing missing from your relationship—real, genuine feelings.…

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What to Expect When Your Wealthy Older Boyfriend Says You “Need to Talk:” Part 1

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age gap datingThe entire week after my big health scare (I had a cyst on my ovary), my older man Keegan nursed me back to health. He took care of me, fed me, and washed my laundry. (Well, he tried and ruined a few things, but he tried and that’s what matters.) Keegan went all out so that all I had to do was rest on the couch. It was way above and beyond for such a minor medical issue, but this was such a defining quality in him that I took notice. If we were to ever have kids, if I ever could have his children, I wondered if he would be so attentive, caring, tender, and helpful.…

The post What to Expect When Your Wealthy Older Boyfriend Says You “Need to Talk:” Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

Proof That Mother’s Day Could Be Bad For Your Marriage

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top_reasons_may12_14Mother’s Day comes around every second Sunday of May and every year, more women are left feeling disappointed and disgruntled. That’s why the Monday after Mother’s Day is when a lot of committed women seem to seek satisfaction outside of their marriage or relationship, like with an affair. A popular dating web site designed for individuals seeking out an extramarital affair has found that after Mother’s Day, there’s a significant spike in the number of women who are signing up.…

The post Proof That Mother’s Day Could Be Bad For Your Marriage appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.


What to Expect When Your Wealthy Older Boyfriend Says You “Need to Talk:” Part 2

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age gap dating“I want to have a large family with you, with a nice house in the suburbs, a wraparound porch, and a nice yard with two dogs to play in it,” I said smiling. “Vivian, that sounds lovely, but there is a reality here that I am worried you are not taking into consideration,” Keegan responded holding the bridge of his nose and crinkling his forehead. “I understand fully. I will be winding up my career, as you are winding yours down. I will be at the height of my career, when you are retired.…

The post What to Expect When Your Wealthy Older Boyfriend Says You “Need to Talk:” Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The Loser I Dated Before I Realized I Needed to Start Dating Older Guys: Part 1

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age gap datingAt the young age of 18, I met a guy named Jared while on a trip I took with my mom and sisters. At six feet with dark brown hair and eyes, Jared wasn’t exactly the dreamboat I wished for. He was a guy who didn’t finish school and was unemployed, still living with his mom. That doesn’t look good to any mother, especially one with a daughter who was unemployed herself; so my mom definitely had some doubts about us. But what my mom didn’t understand was that where she saw a good-for-nothing guy, I saw a potential “dreamboat,” just one that needed a bit of work.…

The post The Loser I Dated Before I Realized I Needed to Start Dating Older Guys: Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

This Is Probably Why You Want to Cheat on Your Older Man, According to New Research

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top_reasons_may15_14There has been so much research on the topic of affairs, specifically why some people are more prone to cheating than others. For instance, one study recently revealed that people who are narcissistic about their sex life and skills are more likely to have an affair. And other research by a dating web site for aspiring cheaters has found that more women tend to seek out affairs the day after Valentine’s Day and Mother’s Day, because they feel disappointed and underappreciated. Another dating web site for people seeking out affairs has done some research of their own into why women cheat, and the results are pretty surprising—almost three-quarters (73%) of the 6,000 female members polled said that they had an affair simply because their partner had certain character flaws and behaviors that annoyed them.…

The post This Is Probably Why You Want to Cheat on Your Older Man, According to New Research appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The Loser I Dated Before I Realized I Needed to Start Dating Older Guys: Part 2

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age gap datingMy spring fling with Jared slowly started to fizzle out. The lust we had for one another was just that, lust. No matter how hard I tried to reform him, he was still grasping hard on his immature side with no hope of ever growing up. School was a big issue for me and I didn’t realize how much of an issue it was until I saw how strong Jared was against it. The fact that he didn’t even graduate with a high school diploma was a major turnoff, not to mention embarrassing, for a girl who was planning to pursue her Master’s degree.…

The post The Loser I Dated Before I Realized I Needed to Start Dating Older Guys: Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The Shocking Thing My Sugar Daddy’s Grandma Said to Him About Dating a Younger Woman: Part 1

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may december relationshipsMy older man, Keegan, had just told me that it was time for me to meet his family and I was freaking out. Our relationship was great, but he made it very clear that they might not be very receptive to our big age difference. I decided to call my mom to ask for some advice about meeting his family. After all, there was a big age difference between her and my father, so I figured she could share some of her own experience. She wasn’t much help though, because she never had to deal with meeting the parents of her older men, most of them were dead by that time.…

The post The Shocking Thing My Sugar Daddy’s Grandma Said to Him About Dating a Younger Woman: Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

Beware: Dating a Man Your Age Could Ruin You

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Dating a Man Your Age Could Ruin YouIt had been a week since I left Jared, my spring fling. After spending two months in Oregon with him, I was ready to start getting my crap together. The first thing on my list was getting enrolled in school again. In the time that I was in Oregon, I had missed the deadline for re-enrollment. Hoping that there was something my counselor could do, I called and he only confirmed that I had to wait till the spring semester. So, there went that, another semester out of school missed. My moods were depressive every now and then, especially when I thought of all the plans that I had made with Jared.…

The post Beware: Dating a Man Your Age Could Ruin You appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The Shocking Thing My Sugar Daddy’s Grandma Said to Him About Dating a Younger Woman: Part 2

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may december relationshipsAs we settled into the guest bedroom of his grandparents’ condo, Keegan was feeling frisky, but I wasn’t into it. For the first time, something was completely suppressing any resemblance of my libido. Keegan thought it was hilarious, but I certainly did not. I had no idea what was going on! Normally, I didn’t give a hoot what other people thought of me, but for some reason, I started to care about his family, what they thought of me as his partner and  someday his wife. We weren’t engaged yet and I knew that we never would make it to that stage if his family disapproved.…

The post The Shocking Thing My Sugar Daddy’s Grandma Said to Him About Dating a Younger Woman: Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.


Why I Was Absolutely Terrified After I Broke Up with My Sugar Daddy: Part 1

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age_gap_dating_may26_14After his cousin Richard’s wedding, my older man, Keegan, and I were so loved up and comfortable because of and in spite of our age differences. We both knew that marriage, kids, and a house were in order for us, but it didn’t come in quite that order. We had been house hunting together, but since I was well seated in my career, I insisted that I absolutely had to buy my own first home, by myself, without his money or jointly with him, in case things didn’t work out due to our age difference. I had an offer accepted on a duplex in a small community with a good school district; we were both very excited about it.…

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Is Your Older Man Naturally Wired for More Sex?

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age_gap_dating_may27_14Age-gap dating isn’t always easy, and adding sex to the mix can sometimes make May-December relationships a little more complicated. A lot of people assume that the only reason an older man is interested in dating a younger woman is because of the sex—the assumption that the younger and hotter she is, the wilder she’ll be in the bedroom. That’s hardly the case. For a lot of age-gap couples, sex might be part of it, but it’s hardly the foundation of the relationship. Through dating different people, you may have come to realize that the value of sex differs from one relationship to the next and from person to person.…

The post Is Your Older Man Naturally Wired for More Sex? appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

Why I Was Absolutely Terrified After I Broke Up with My Sugar Daddy: Part 2

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Why I Was Absolutely Terrified After I Broke Up with My Sugar Daddy: Part 2I was pregnant. I was pregnant, single, and living in a crappy little apartment. I was terrified. The entire next day, I just slept. I was probably exhausted because of the pregnancy. I had scheduled a doctor’s appointment to begin prenatal care and was thinking of ways to tell Keegan he was about to become a father out of wedlock. That evening, I started to bleed. Immediately taking myself to the ER, I texted Keegan to please meet me there. He beat me there, but because we weren’t married, security wouldn’t allow him back without my permission.…

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How My Best Friend Set Me Up For My First Sugar Daddy/Sugar Baby Relationship

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How My Best Friend Set Me Up For My First Sugar Daddy/Sugar Baby RelationshipThe holiday season was soon coming to a close, and with that, so was my seasonal position at a retail store in the mall. As my first job and first step in getting over my summer heartbreak, I was ready to go back to school. With one week before January, my enrollment appointment was fast approaching, and soon I would be able to go back and finish the spring semester of my freshman year in college. But before I went back to school, I needed to make sure that I had my best friend back. How was I supposed to go through college without having Melinda there right beside me?…

The post How My Best Friend Set Me Up For My First Sugar Daddy/Sugar Baby Relationship appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

The Most Incredible Surprise My Rich Older Man Ever Planned For Me

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The Most Incredible Surprise My Rich Older Man Ever Planned For MeIt was dark, it was the middle of winter, and me and my older man, Keegan, were cold, but we snuggled on a bench overlooking the water. All we did was talk and laugh, but it was perfect. The entire time, Keegan was anxious and edgy. It was starting to creep me out. There were tourists taking pictures and the next thing I knew, there was a quartet of violinists playing on the balcony of a home across the street from where we were sitting. I immediately started crying, as I realized upon turning around that Keegan was proposing to me.…

The post The Most Incredible Surprise My Rich Older Man Ever Planned For Me appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

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