“Wait, your boyfriend is the same age as your dad?”

By: Laura C. Anderson

Let’s talk about sex. Let’s talk about sex and relationships. Let’s talk about sex and relationships for the couples out there that aren’t exactly dating within their generations. You know what I’m talking about here – the Hugh Heffner’s and Mary-Kate Olsen’s of the world. It's no surprise when we see a couple with a significant age gap we can’t help but be overly curious why they’re together. Is it for money, for sex, dare we say for love? I needed answers so naturally I went out got them. Read below to learn what it’s really like dating men and women significantly older or significantly younger. I won’t lie; some of these experiences are a little spicy. 


The Cougar

Meet Sharon. She’s 46 and she’s dating a 29 y/o former student named Ben*.

So Sharon, how did you and Ben transition your relationship from teacher/student to girlfriend/boyfriend?

“Well, I’m a professor at USC and a few semesters ago while teaching one of my masters courses I had a grad student who I noticed would spend a little extra time getting his things together before leaving class. He was always first to arrive and always last to leave. A few times he asked if I could privately tutor him, and before your mind goes to some porn fantasy, we were always in the tutoring center surrounded by other professors and students. It wasn’t actually until after the semester was over that we saw each other out downtown. He approached me while I was heading into a store and though I was excited to see one of my former students I couldn’t help but notice there was something different about the way we were interacting. I never thought in a million years a young, attractive guy in his twenties would be interested in dating a much older woman but before we knew it we had plans to grab dinner together later in the week – and, well – the rest is history.”

Do you ever feel like his mom?

“No. He’s actually the dominant one in the relationship. He pays for me and takes me out and takes care of me just like he might for any girl his age.”

What does your family think?

“I actually have a daughter who’s 26 and made sure I discussed the situation with her before pursuing anything at all with Ben. If she was uncomfortable with the idea of her mom dating someone close to her age, I never would have considered it.”

What do you have to say for other older women interested in dating a younger man?

You shouldn’t let age determine who you do or don’t date. Everyone is at different maturity levels and everyone has their own desires or expectations from a relationship. If the two of you click then go for it.”

'Hugh Hefner'

Meet David. He’s a 55 y/o orthodontist dating one of his 26 y/o patients named Jess*.

This is quite the age gap, David, do you ever notice people staring or making comments about you two in public?

“Absolutely. I’m pretty positive everyone thinks I’m Jess’s Sugar Daddy, especially because I’m an orthodontist.”

Are you her Sugar Daddy?

“Ha, no, not by any means. I buy her things and pay for our dates the way any man might spoil or treat his significant other.”

What does her family think of her dating someone old enough to be her father? Better yet – what does her father think?

“To be honest, it took months before we broke the news to her family. Her father was in the military and very traditional in his ways. He saw me as a friend when we first met and asked me to play golf with him. I respectfully declined and the next day we told him the news. I thought he was going to get me fired but over time he saw how respectful I was toward his daughter and how great I took care of her so he came around, sort of.”

And how’s the sex? 

“For me, amazing. I get to enjoy a bubbly, energetic, tight 26 y/o! She says it’s great for her because I’m experienced and I know what I’m doing but I know I don’t last as long as most boys her age.”

'The Pool Boy'

Meet Nicholas. He’s a 24 y/o electrician dating a 44 y/o business-owner named Deborah*.

So Nick, can I call you Nick? What's it like dating a cougar?

“Ha, it’s different for sure. Older women are like fine wine in my opinion.”

Meaning they only get better with age?

“The right woman will, yes. Deb is vivacious and she acts young for her age. Ugh, I hate even saying ‘for her age.’ Age shouldn’t be a factor. She looks 30.”

Does anyone ever say anything negative about the two of you being together?

 “Not at all. I think it’s a little more taboo and controversial for a younger girl to be with an older guy. No one thinks twice about a younger guy with an older woman.”


 “Our experiences together have been nothing but positive. I think girls have it harder than guys.”

Tell me about your sex.

“It’s through the roof. I’m great in bed, or so I’ve been told, and she’s beautiful and maternal and so focused on pleasing me and making sure it’s enjoyable for me. We’re crazy about each other, how could the sex not be amazing?”

Ever live out any role-playing fantasies?

“Honestly our whole relationship feels like a giant fantasy so…”


Meet Jennifer. She’s 23 and dating her 40 y/o boss, Craig*.

Alright, Jen, let’s be real, usually everyone gives the young doe-eyed girl shit for dating an older, well-off man. Is that the case for you?

 “It is and it isn’t. Some people are definitely judgmental and they’ve made up their minds about why I’m with him. I’m not going to waste my time convincing anyone of anything. I’m with Craig because I’m happy with him. End of story.”

What do your friends say?

“They know I feel so protected with him. I’m always telling people he looks good for his age, which he does. My girlfriends call him my ‘Salt & Pepper’ or ‘Silver Fox’ and it always makes me laugh.”

What does your family think of you with someone twice your age?

“They are surprisingly supportive. They know I wouldn’t date someone who didn’t treat me well. Plus we just work well together. Our personalities compliment each other.”

 What do you notice are the biggest challenges dating an older guy?

 “I think we have less in common. We come from different generations. A lot of the time I feel like the young club-hopper who wants to stay out until 2 a.m. and Craig will have work early in the morning and want to hit the sheets by 9:30 p.m.”

What do you notice works in your favor?

We appreciate each other. I know Craig feels so damn lucky to be with me. I’m young and hot and he knows the chances of getting a younger woman like me again are slim to none. Meanwhile, I adore how well he treats me. He’s old enough to know a good woman when he has one, unlike the douchey guys my age.”

Tell me about your sex.

It’s not mind blowing but it’s also still satisfying. He doesn’t last as long as I’d like and he isn’t that well endowed but he is passionate and responsive and I love the way he handles me. Overall it’s a 7/10.”

Laura C. Anderson | @s0mebl0nde



Contact Us                       Magazine Advertising                  Our Team                              Subscribe  

Careers                            Privacy Policy                               Clients & Affiliates                 Media Kit     

Model Safety                   Cookie Policy                               Services                             



© 2014 Creative Demand Network., All Rights Reserved