Are Secret Admirers Freaky Or Fantastic?

NY Post columnist Ashley Dupre gave some advice to a man who wants to impress a co-worker he has a crush on. She says

[Y]ou should try something creative to let her know how you feel. Since you’re friendly and have gone out before, you’re probably aware of some of her favorites: flowers, lunch spots, snacks, etc. I think you should send her things spread out over the course of a week. Sort of like a secret admirer. Start on Monday by leaving her an arrangement of her favorite flowers. In the card, write something like. “You know me and I know you, but I’d like to get to know you more.” Let her be curious for a day, then on Wednesday, leave her a little something from her favorite lunch spot or a coffee place she goes to for a midday pick-me-up. With this one, get a little more personal in the card, and also give her some clues as to who you are. Finally, on Friday, leave a simple Post-It on her computer when she’s not looking that says something like, “Have I driven you crazy enough? Let’s meet so you finally know who I am (unless you’ve already figured it out!)” Tell her you’ll be waiting on a certain day and time at a certain place with a single red rose. (I know this sounds cheesy, but I’m telling you, women go crazy for this stuff!)

The girls over at Jezebel claim that this is Ashley’s worst advice ever and “if by “crazy” she means “scared that I’m being stalked at work,” then she’s right on.”

I don’t actually hate this advice as much as the people at Jezebel do. I once had a secret admirer who sent me poetry and flowers in college. It was pretty cool. Trying to figure out his identity was like trying to solve a mystery, a romance mystery where no one died. He wasn’t really that into me once we actually went on a date. I think we both liked each other more when there was no actual interaction between us, which stuck me as being the biggest downside to the whole “secret admirer” thing.

Lilit hasn’t had one, but she thinks the biggest downside is probably “they’d turn out to be ugly. If they weren’t ugly, why wouldn’t they just approach you straight out?” Because there’s this thing called romance. And they want you to love them for their words, maybe.

Meanwhile, our intern Jillian says, “In second grade I got a letter and a key-chain from King’s Dominion. Then my gym teacher found out and said “this is not okay.” That gym teacher watched his afterschool specials.

Our marketing director Amanda says that “My freshman year of high school my friend gave me a drawing he had done of me to the boy I was dating. It wasn’t really a secret admirer, but he was stalk-y drawing me.” Then he chopped off his ear and sent it to her, because that’s what artists do.

Admittedly, a lot of these things have to do with nuance. You’ll probably be more receptive to a letter that doesn’t allude to “driving you crazy.” Maybe secret admirers could make a joke and sign it “your super stalker!” No, maybe that wouldn’t be funny. You don’t know that the girl has never been stalked. I don’t know. Have you ever had a secret admirer? Was it creepy? Do you think there’s a way to make it non-creepy? Let us know, and maybe we’ll send some anonymous flowers to your workplace.

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    • porkchop

      I think not-so-secret-admirer is the only way to keep from being creepy. I once told a coworker that I was sad and cranky because I missed breakfast, and he bought bagels for the entire office. It was a really nice gesture and only I knew that it was for me. It was really nice.

    • lj

      I find secret admirers creepy and loathsome and the fact that this is at work makes it worse. Work is supposed to be your safe place so the fact that you can’t tell this person to stop just seems like some form of abuse. You can’t follow up with HR, should you want or need if it crosses the line because how would you report it?

      Besides, if a guy doesn’t have the guts to approach me with his name, why would I be interested?

    • Judy

      Keychain? I must have missed the after school special that explains it…

    • Pali

      This is a tricky one. I think it can be super sweet if it doesn’t get too intense and doesn’t last too long. Her suggestion of doing it for only a week is probably a good idea. And don’t reveal yourself by making her confront you in person; leave a card or a note (or something more creative) and wait for her to contact you. Basically, make it small but sweet, not too stalker-ish, and easy for her to ignore, and it could go over well. Depending on the girl. And maybe don’t do it at work.
      I had a sort of secret admirer once. He was sending me anonymous poetry on my Facebook Honesty Box (hey, we were still in high school). At first I was flattered (even though the poetry was kinda bad), but the poems kept getting more and more intense and I started getting worried. After a while I came to my senses and recognized the writing style as a friend I knew had had a crush on me for years, someone I unfortunateky had NO interest in whatsoever. This became super super awkward and difficult for me.