This is a major lesson we can learn from Taylor Swift’s relationships and lyrics.
Taylor’s love life has been on full display since 2006, which means we have about two decades worth of lessons to consider.
Avoid dating with too big of age gap.
As in, what happened in Taylor’s relationships with John Mayer and Jake Gyllenhall. Taylor is currently engaged to marry Travis Kelce who was born in the same year as her (1989), but in the past, she’s had relationships with men who probably shouldn’t have been traumatizing her with their older ages and manipulation. She dated John Mayer when she was 19 and he was was 32, and their 13 year age gap did a number on her. In her song “Dear John,” she sings, “Dear John, I see it all now that you’re gone. Don’t you think I was too young to be messed with? The girl in the dress, cried the whole way home. Dear John, I see it all now, it was wrong. Don’t you think nineteen’s too young. To be played by your dark, twisted games when I loved you so? I should’ve known.”
The reality is that she shouldn’t have known. At 19 years old, you’re young and naïve. You live your life with childlike wonder, naïve beliefs, and unrealistic expectations about what a fairytale happily ever after might feel like. Older men know this about younger women, and so therefore, they often prey on younger women who they see as easy targets. It’s easy for older men to get exactly what they want from younger women because they know the way younger women idealize situations, hope for the best, and look at everything through rose-colored glasses. Taylor used those lyrics to highlight the mental games John Mayer played with her, describing his actions as a chess game where he would change the rules every day.
She also described her blind optimism, which is something young women tend to have before getting exposed to manipulation from their first relationship with a master manipulator. Now let’s talk about her relationship with Jake Gyllenhaal. They met when Taylor was 20 and Jake was 29, which means they had a nine year age gap between them. In “All Too Well” the 10 minute version, she sings, “You said if we had been closer in age, maybe it would’ve been fine. And that made me want to die.“
Based on the lyrics, it sounds like Jake felt like their relationship could’ve gone further if they didn’t have nearly a decade of an age difference between them. From her perspective, she was still willing to try and make it work, even though their age gap meant they were at completely different stages in life. At another point in the song, Taylor sings, “I was never good at telling jokes, but the punchline goes: I’ll get older, but your lovers stay my age.“ Although her relationship with Jake ended, he continued dating girls who were much younger than him, even though he complained about that being an issue he had while dating Taylor specifically.
His current girlfriend is a French model named Jeanne Cadieu, who is 16 years younger than him. She’s currently 28 as of this video publication and he’s 44. So, just like Taylor sang in the song, his girlfriends have remained much younger than him as years have gone by, even though Taylor has continued to grow and evolve beyond their failed connection. And that’s not to say Jake hasn’t grown and evolved too, he just hasn’t explicitly expressed his feelings about everything the way Taylor has done in such an open and vulnerable way in the lyrics of “All Too Well.”
From personal experience dating much older men in my early 20s, I do personally feel that young women can avoid a lot of heartbreak and turmoil if they avoid dating older men who have so much more life experience. When I was 19 years old, I dated a man who was in his early 30s, and he ended up being the most toxic, manipulative, and abusive partner I could’ve ever dated. He used charm to weasel his way into my life, and once he got me completely isolated, his true colors came out after I felt like I didn’t have friends or family to turn to anymore. After that relationship ended, I dated another man who was 20 years older than me, and that relationship didn’t turn out very well either. I was 22 and he was 42 years old when we met.
I reflect back on both of these relationships with a lot of regret and sadness that I allowed myself to be in those types of relationships in the first place. Fast-forward to today, and I’m married to a man who’s my own age. Being married to a man who’s my age mate is really special to me because we share so many things in common, including our matching life experience level. We went to middle school at the same time, so we both enjoy the same era of music and entertainment. We have the same energy levels when it comes to traveling together, going to nightclubs for date nights, and generally socializing with friends, which is something I didn’t experience when dating much older partners.
I do also want to throw it out there that it’s possible to have a healthy relationship with someone who is much older if both people are healthy-minded individuals. I just attended one of my close friend’s weddings, and she actually married a man who is about 20 years older than her, and he loves her so passionately that their marriage makes so much sense and they wouldn’t have it any other way. She respects him and he adores her, and their age difference is nothing more than a minor detail in their love story. So while it’s probably safer for young women to avoid relationships with much older men in most cases, it is still possible to find those rare golden gems where it actually works out for the best and the relationship is genuinely healthy and happy.






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