Is Her Valentine’s Day Plan Cute or Creepy-Stalkery?


A reader named Charlotte has a crush on her local bartender (what is it with those guys and crushes? Is it the fact that he washes the dishes? The access to quality alcohol? What is it?) She’s got an idea for a Valentine’s Day gift, and she’s wants to play that game show that’s been sweeping the nation…
CUTE!
OR!
CREEPY!!!!
Let’s spin the big wheel, shall we?
Hi Jeff-
Big fan of your site! I’ve whiled away countless hours at work gleaning your pearls of wisdom. So here’s the deal, there’s this bartender that I have a HUGE crush on.
He flirts with me.
I flirt back.
Sounds fun so far…
I’m not sure whether he’s flirting because he’s interested or if he’s flirting because he’s a bartender and probably flirts with tons of women.

He is most likely aware that I like him since I’ve mentioned it to a couple of his co-workers.
Mmm…don’t be so sure. If his co-workers are dudes, maybe not. We don’t always, always share that kind of information. You know, at the man meetings.
I’m too chicken-shit to ask him out though. I figure if he was interested, he’d ask me out. This has been going on for about eight months though.
That brings me to question - what with Valentine’s Day coming up I thought why not send him something? I was thinking about sending a really cool bouquet of Origami flowers with a little note to the bar where he works.
Something along the lines of, “Happy Valentine’s Day from your somewhat secret (and hopefully not creepy) admirer!” Signed with my first initial.
So here’s the question Jeff, is that gesture creepy and stalker-ish ?
Or cute?
Your opinion would be greatly appreciated.
Dear Charlotte,
Ok, let’s look at your plan, and see if it comes up cute or creepy. Well, no. Whatever the result, it won’t likely be the PLAN that is either one. Lemme ’splain.
MALE GIFT RECEPTION ‘SPLAINED
Here’s the thing, it doesn’t matter what you do for him or give him. If a guy likes the idea of dating you, it won’t matter what you got him. In that situation, everything is cute. He’ll just be happy that you like him. (Unless it’s a severed head or a creepy picture you took of him sleeping alone in his apartment or something.)
And the opposite is also true. If he isn’t at all interested, there will be no gift that won’t freak him out a little.
Just like when a guy checks you out. If you think he’s hot, it’s sweet. If he’s creepy, how DARE he!? Right?

SO…CUTE? OR CREEPY?
Given all of that, here’s my assessment of the situation. I think the secret admirer thing is likely not a good idea. This could just be a bias that I have against secret admiration, sure. But here’s why I think it’s not necessary, and potentially a lousy idea. Here are the possible reactions, if he figures out it was from you:
  1. Hurray! It’s from HER! — In which case, the secret part wasn’t really necessary in the first place.
  2. Oh crap! It’s from HER? — In which case, WOW, will it seem creepy-stalkery.
And what if he doesn’t figure out it was from you right away? Well, it’s going to build up and up and up. And he’s then gonna find out the truth. And either he’ll be…
  1. Just as totally psyched as if it hadn’t been secret in the first place, OR…
  2. Just as NOT psyched as if you had sent him a severed head.
Now, maybe it’s just the coward in me, but that seems like too much potential for weapons-grade awkwardness. Awkwardness of the “I can never set foot in there again” variety. And unnecessary awkwardness.
NO MORE SECRETS
Here’s what I say. Don’t be a secret admirer. Be a proud admirer. Keep your whole operation as is, but change it slightly so that it’s:
“Happy Valentine’s Day from your no-longer-secret (and hopefully not creepy) admirer!”
And then sign your actual name.
Why? Because it’s less weird. If you go the “secret admirer” route, it builds it up. Maybe too much, given that you don’t even know where he’s at with the whole thing.
Remember, if he’s interested, the lack of a secret won’t diminish the fun. And if he’s not interested, well, it certainly ain’t gonna make it less creepy. And given that you’re not 9 years old, the secret WILL have to be un-secret-ed at some point, right? So I say, pre-un-secret it.
I know, I know. You’re too chickenshit to do it. Yeah, well, believe me, whatever bad result you’re afraid will happen if you are direct with him? Yeah, it’s pretty much got the potential to be 10 times worse if you build it up as a “secret” and it doesn’t work out, so you’re not any “safer.”
Just do it. Because a.) you’ll find out right away what’s what, b.) if it’s not what you’re hoping for, it will be less awkward, and c.) if it’s exactly what you’re hoping for, it will be exactly as awesome.
Just do it, Charlotte. Leap before you look. Worst case? He’s not interested. At least you’ll be in close proximity to some soothing booze.
Do you agree, ladies? Secret Admirer is cute or creepy?

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