Introducing: Ask a Fuck-up

Our new advice columnist refuses to learn from her mistakes, but maybe you can.

Introducing: Ask a Fuck-up

Our new advice columnist refuses to learn from her mistakes, but maybe you can.

Brandy Jensen, The Outline’s social media editor, has made a lot of mistakes in her life. Has she learned from them and become a wiser person as a result? Hahaha oh gosh no. But it does leave her uniquely qualified to tell you what not to do — because she’s probably done it.

Dear Fuck-up,

I fear I’m unintentionally the main character in a messed-up Nicholas Sparks film.

I’m in college and work part time at a whiskey bar (it’s like hooters but with cowboy boots) and I’m falling in love with one of my regulars. He’s in the Air Force and is about 10 years older than me. He’s handsome and kind, generous, gentle but masculine, super funny and affectionate. He is super intelligent, and has two masters degrees (history and education). He’s a gem!!!! I didn’t think men like this actually existed.

I on the other hand am a junior in college, intending to pursue dental school following graduation. I live with my parents, lol, and am super boring because school is my whole life.

The caveat: he moves back to Italy, where he’s stationed, in a month and a half.

I don’t know what to do?? I’m totally in denial about my impending heartbreak. My best friend adores him but thinks I need to cut ties prematurely so it doesn’t hurt so bad when he leaves. But I love him. I haven’t told my parents about him because they’re incredibly overprotective and wouldn’t like the age difference, though I think they would like him as a person. I’m at a loss. Any advice?

All the best,

Dear Stuck,

What a perfect question for the inaugural Ask a Fuck-up. It references so many things I myself have made a complete and utter mess of in the past. Falling for charming bar regulars! Older men! Guys who live far away! I once followed a man to Australia only to be promptly informed he had a girlfriend. Hopefully that’s the last time I will cross the International Date Line to fuck something up, but who knows. Anyways, onto your question.

Here’s the good news, Stuck: You are most assuredly not in love with this man. In a few years’ time you will not look back on this man as one of your life’s great romances. How do I know this? Well, that your romantic frame of reference is a Nicholas Sparks movie is a pretty big clue. Do they even fuck in those? No, they just hide away in little hamlets where only white people live.

But right now you think you’re in love so me telling you that isn’t true won’t make you feel any differently. Had you been writing to ask if you should start dating this man I would have told you no, but that’s not your question. Your question is if you should stop. And who are we kidding here? You are not going to stop. So, much like hangovers in your thirties, this situation is no longer about how you can avoid the pain but how you can mitigate the damage that has already been done.

Luckily, there’s another bit of good news: This man you are not in love with lives in another country. I know you think this is the root of your problem, but it’s actually the solution. Enjoy your month-and-a-half of flinging with a charming older man and then, once he leaves, tell yourself that he has found love with an Italian model or joined a monastery. He does not exist to you anymore. Trust me when I tell you that a dramatic but definitive end to a relationship is preferable to the slow accretion of anxiety when he starts taking more and more time to respond to your emails or to watch your Instagram stories, or to acknowledge your existence at all.

And yes, this is going to hurt for a while. But then it won’t as much, and you will realize that heartbreak doesn’t kill you, and you will go out and break your heart again, hopefully with someone who lives in the same time zone, or even zip code, and is able to make the same cultural references you are. Because the final bit of good news I have for you is that this man is nowhere near as wonderful as you find him to be right now.

I am going to share an insight it took me altogether too long to realize. When you’re in your early twenties and older men are interested in you, it is not a flattering reflection of your own wit or intelligence or maturity. Rather, it’s more likely an indication that these men have neither the ability or the inclination to date women who have figured out what they want and how to ask for it. There are exceptions, of course, but here’s the rule: you’re not exceptionally interesting, they’re just tedious. Keep that in mind and a lot of the older-man charm wears off.

A Fuck-up

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