Secret Confession: I Dated An Older Guy

taylor swift is notorious for dating older guys

When Taylor was 19, she dated John Mayer who was 32 (and a jerk!) | Source: INF Photo

When I was 19, I was dating an older guy–and when I say older, I mean really older. He was 30!

Often when people hear this, they think he took advantage of me, or that he was preying on young girls–but the reality is that I sought him out. I saw him at a dance club one night and thought he was super beautiful. I marched up to him, told him I thought he was cute, and from the minute we started dancing until the end of that summer when I moved abroad for school, we were inseparable.

He was really popular in the club scene, so a ton of people knew him (or at least knew of him)–but a lot of people worried about me being with him, and not just because they didn’t like me dating an older guy! My elder Romeo had a pretty bad reputation. He’d been married and divorced already, was a recovering alcoholic, was known to do drugs, and it was rumored he’d slept with just about every girl in town. I knew all of this, and the truth is, that’s exactly why I wanted to date him.

Up until then, I’d only had two real boyfriends–both of them were super sweet and so good to me–but both of those relationships were so serious. I wanted to finally date someone just for fun–just to go out and make out and have it not be this whole dramatic epic romance. I thought with this guy, it definitely wouldn’t be. Plus, I loved how dangerous he seemed. He was exciting in a totally different way than the boys I’d dated before.

taylor swift and jake gyllenhaal he was the older guy

When she was 20, she dated Jake who was 29! | Source: INF Photo

Looking back, I definitely put myself in what could have been a scary situation. Being as inexperienced as I was (did I mention I was still a virgin?!), he could have totally manipulated me into all kinds of things–but lucky for me, this guy with his Big Bad Wolf reputation treated me like a princess. I was so determined to live on the edge for once, but instead of taking me up on it, he was uber-protective of me–making sure I never ever got into trouble or felt threatened. When we went to wild parties together, he’d whisk me away to the kitchen and cook for me–that man made great pancakes. And when I told him I hadn’t had sex, he respected that. Sure, he asked if we could (and I think he knew I was thinking about it!) but he never made me feel like I had to sleep with him.

It all made sense–and came to a very disappointing end–when he finally admitted that he’d fallen in love with me. That he hadn’t loved anyone as much as me since his wife. Here I was looking for my first no-strings fling, and Mr. Dangerous had turned into a big, mushy “I want a commitment” puppy dog. Woah. This was way more than I was looking for–and more than I could handle.

Luckily, I already had plans to leave The States and study abroad that September, so I had an easy out. Over the years, I’ve looked back on those few months with him and although I totally understand why I was into it, and what I was looking for in that relationship–I still can’t quite understand what was in it for him (of course, besides my sparkling personality and drop-dead looks–I kid! I kid!). Maybe I made him feel younger? I have no idea.

The bottom line is, I was really fortunate that he was so good to me at a point where some really bad things could have happened. A lot of guys who date girls that much younger than them are predators. I know girls who’ve dated much older guys and been completely taken advantage of.

Obviously I can’t tell you not to date an older guy after telling you a story like mine–but if you are, or if you’re thinking about it, just make sure he’s really respectful of you, that you never feel forced into anything, and that your friends or family know about him and know where you are. I don’t have any regrets, and I don’t want you to, either.

Have you ever dated an older guy? Are you dating an older guy right now? What do you think about an 11-year age difference? Tell me everything in the comments!

Are You Into Younger Guys? So Is This Girl!


Posted in: Love Advice, Relationships
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33 Comments

  1. avatarPhelisa says:

    It is wrong to date a sugar daddy because they bring lot of diseases

  2. avatarlenna says:

    One thing that I hate about my dating life is that Im 19 and my bf is 38 and noone knows that we are dating. Its frustrating because he met me at a younger age, but over the years we started falling in love with each other. He is sweet,smart,handsome and treats me so well never controlling or anything in that matter. I also never dated, he was my first bf and I feel like his family thinks im using him because they always see me with him. I dont know if i should be with him?

  3. avatarchastity says:

    Turning 15 I fell in love with this gorgeous guy who was 32. Many will find this ridiculous. A week before I turned 15, I lost my virginity to him. I was curious and adventurous and he wanted me sexually. I knew that because he told me. He was so sexy and I liked the way he took control and made me feel I was in heaven. I didnt mind experimenting sexually because I knew I was safe with him. It was extremely exciting and we had plenty of sex on a very regualr basis. I used to rush to his place everyday after school to have sex. Sometimes even before school I would lie to my mom that I needed to go early and I would go to his place.
    When I turned 16 he told me that he wanted me to be sure that he was the one I definitely wanted to be with and allowed me to go out and have fun and explore and date other guys just to understand if I still wanted to be with him or not. He asked me to promise him that I would make sure I was safe and would use condoms if I had sex with any other guy. I did have sex with 5 other guys. Two of them were my age and the other 3 were slightly older. I was 16 but I was having so much sex. I enjoyed it but something was missing. I felt a kind of emptiness and a longing for that something that was missing.
    Because of this, I was thoroughly disappointed with the younger guys and the guys my age. They were so immature and inept, had no way of making a girl feel good and didnt have a clue about what I needed.

    I longed for my older bf. After spending 6 months with various guys I went back to my good ol’ faithful. I have never missed him so much in my life. The love making was just divine, the sex just awesome, his whole manner and endearing, patient attitude towards me was so refreshing. I felt so guilty that I slept with other guys and I decided to introduce him to 2 of my best friends who also wanted to have sex. I knew they liked him because they used to come with me to his place and they really thought he was very attractive. We experimented with 3sums and a lot of other stuff.

    I am 19 now and am still with him. He is 36 but I dont care about his age. He is gorgeous still and to me I would never go for anyone my age. The younger guys are too childish and immature.

    My experience with an older guy has been the best. I will never change that for all the gold in this world.

    • avatarliana says:

      That is so sweet. He let you actually go with other guys? wow!! that is so cool.
      I dont mind age too. I started very early too and I was always with much older guys. Many of my guy friends have asked me why I dont go with guys my age. I just find older guys a lot more attractive and interesting. I know they like sex with us but I know guys our age like sex too. I dont see what the big deal is and why everyone makes such a fuss. Sex will happen if you like the guy. So what if he is older. Do those older guys not have emotions and feelings? So why is it wrong for an older guy to want to have sex when he has a younger girlfriend? To me it is not wrong.

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