Dear Annie,

I have a bad habit of dating men who are 10 to 20 years older than me. But they break my heart every single time *surprise surprise.* I am intimidated by guys my age because I feel like I’m not good-looking enough for them. Older men just approach me more, but they seem to have no respect for me at all. How do I continue seeing older men and keeping my emotions safe?

Help,
Taylor Swift, All Too Well Fan

Dear Taylor Swift, All Too Well Fan,

For better or worse, nearly anyone with a beating heart can relate to global superstar Taylor Swift’s music. Her discography includes a plethora of songs about older men breaking her heart, but she also has ballads about men her own age upsetting her. Whether they’re your “Dear John” or “Mr. Perfectly Fine,” dating anyone can lead to heartbreak.

But the power imbalance that hangs over a rendezvous with an older man can create a new source of problems that you need to be prepared to handle. With age comes wisdom, or so they say, and an older man could be quick to assume he can set the terms of your relationship. You may find their actions easily influence you, falling under the spell that age equates with knowledge. They have decided to approach you after all. Would you have gone for these older men if they blinked at the first glance?

If you choose to see older men, hold them to higher standards when it comes to valuing your time and emotions. Be picky about communication style and which activities you do together. Let him know from the beginning that your student schedule matters just as much as an adult’s. Do not let him patronize you. Clarifying the level of respect you deserve enhances your agency – though they may approach you, you have the power to choose whether or not they stay in your life.

If they’re at least in their late twenties or thirties, you should expect them to take you out on the town. Dating young suggests they may lack the maturity needed to find partners their own age, so expect them to compensate. The least he can do is plan public dates to show he takes pride in you. Jake Gyllenhaal and Taylor Swift were “always skipping town,” so do not make the mistake of falling for a guy who hides the fact that he’s dating someone still on GWorld. Keeping your affair secret suggests nefarious intentions – he’s not in it for you as much as a private confidence boost. Signal self-respect by refusing to let him hide you away in his love nest.

Beyond the dates they plan, expect them to be more gentle with your feelings and respectful to your needs than a college boy. While college boys are not inherently insensitive, an older man has had more opportunities to develop empathy. College guys may enjoy leading you on to affirm their self-confidence, but an older man should understand you do not exist for a personal ego boost. Never let them shame you for skipping a date to study for your Spanish final or claiming you spend too much time with your friends! Just because they may have a job does not mean your responsibilities as a student and social life independent of the relationship are less important.

Age gaps can make the younger partner feel like they are doing the doggy paddle at the Olympics. Like Taylor Swift in the “All Too Well” short film, you might feel like it’s just an adult thing for him to toss you the car keys instead of driving. But really, that means he likely doesn’t even care enough about you to ask if you want the driver’s seat. Higher criteria may not save you from the pain of a breakup, but it could make the men that break your heart a little better than the douchebags preying on insecure college students.

Forever and Always,
Annie<3

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