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.
Oh, like it can’t be both?
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:
- Hurray! It’s from HER! — In which case, the secret part wasn’t really necessary in the first place.
- 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…
- Just as totally psyched as if it hadn’t been secret in the first place, OR…
- 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?
Posted: January 28th, 2009 under Reader Requests.
Comments
Comment from AnneZ
Time January 28, 2009 at 9:29 am
Sign your whole name, yes. What if he does feel creeped out by some OTHER girl with the same first initial? Or semi attracted to one? you could really sabotage yourself forever before you’re even out of the gate. A) he sets the origami on fire and moves to Puerto Vallarta B) he lovey doveys all up to someone else, she doesn’t really know why but on their silver anniversary it’s a story they tell their grandkids.
I would also scale back the gift. In fact, I’d make it a card. Hopefully a very witty or funny one. Then it’s not creepy and don’t write that part. Just say “you’re so cute–funny–talented–doublejointed. I really would like to see more of you.” Something like that. So he can laugh it off and back off if he’s not really interested and your head won’t explode in flames. And if he is interested, he flirts back with more vigor and plans get made to “see more” of him.
Good luck!
Comment from thursdaynext
Time January 28, 2009 at 11:27 am
Please. Don’t send him origami flowers. Yes, i see where you’re coming from (and it’s a cute gift) but it will come across as creepy and freak him out. I guarantee it. I think guys are weird when it comes to giving them presents. I used to work at a record label & I grabbed a bunch of (free) CDs from work and gave them to a guy i was dating. He said “I think you have more invested in this relationship then i do”. Ok, he was a jerk. But anyway, you’re better off giving him a cool card, then a present. And definitely sign your name. Good Luck 
Comment from The Seductress Within
Time January 28, 2009 at 11:49 am
Forget sending him anything. How will you feel if it doesn’t go well? Silly? Stupid? Embarrassed?
I’m not saying you ‘should’ feel any of these things, but realize it’s possible and why set yourself up or put him on the spot.
What is your goal? To send the message loud and clear that you want him to ask you out?
You can accomplish that in a less risky and sassy, playful, flirty way.
You said you flirt all the time and that you figured if he wanted to ask you out he would. Yes, that’s probably true.
As a bartender he probably does flirt with everyone because:
1. He’ll get better tips
2. It’s just plain fun
3. Bartending is very social and flirting just goes with the territory
4. He thinks you are cute but so what?
5. He thinks you are cute and would like to ask you out.
If it’s #5, turn up the flirting fun dial in a more direct way.
Say things like “I wish you weren’t working right now so you could join me for a drink”,
or in your most playful, cute voice with fluttering eyes, “So do you ever date your customers” followed with a wink…
You get the idea, send the message you are open to his advances that way.
It’s cute, fun and WAY less risky….
If he doesn’t ask you out after that, his reasons for flirting are #1 thru #4.
The Seductress
Comment from Liz C
Time January 28, 2009 at 11:55 am
Ah, Jeff, where were you when I was embarrassing myself in my 20s?
Oh yeah. You were in grade school.
As someone who made that mistake, I think your advice was absolutely correct. And now I have to go crawl under my desk, reliving the shame of that event 25 years ago….
Comment from Charlotte
Time January 28, 2009 at 1:14 pm
Thanks so much for all of the wonderful advice!
Since posing this question to Jeff I purchased his book – BRILLIANT! BRILLIANT! BRILLIANT! by the way.
Anyway, flowers don’t do cool stuff.
Ergo, not a good man gift.
See! I’m learning, Jeff!
I agree that the secret admirer thing is most likely creepy/stalky.
I also think though that putting myself out there like that is absurd.
I have what I think is a good idea…
Why don’t I just do in on Valentine’s Day and wish him a happy holiday?
You know, and like flirt a lot.
Jeff, I’m thrilled that you chose to answer my question.
I hope you don’t think me ungrateful for not following through on sending the flowers.
Comment from murray
Time January 28, 2009 at 1:48 pm
I agree with Seductress. Don’t send him anything at all. Valentine’s day is a while away yet, and it’d be better, I think, to use the time to flirt a bit and get some real sense of what he’s like and whether he likes you in a face to face way, than be preoccupied with a secret communiocation that is weeks away. I’m a guy, and I’d infinitely prefer that scenario to any puzzling card or gift.
Comment from Glen
Time January 28, 2009 at 2:06 pm
Why is it that girls continue to give us guys things that they would want, not us? You don’t see guys giving girls a box of beers or some motor oil!
8 months of crushing on this guy is just stupid – he’s a bartender so flirts with every woman, because it helps get them back next weekend, and sells more drinks. It’s worked on you hasn’t it (8 months at least).
Valentine’s Day is the worst day to do anything about it – it’s so predictable. Stop being a dumb schoolgirl about it, and just suggest you 2 hook-up somewhere that’s not the bar sometime. If he goes for it then he’s interested in you – if he says anything else (“I’m too busy”, maybe some other time” etc etc) then he’s not into you.
Origami flowers would be gay (in the ‘it’s a stupid idead’ way, not the ‘I like the same sex’ way).
Comment from K-Rod
Time January 28, 2009 at 3:30 pm
I totally agree with Seductress. Do that, save your $, and you’ll know. I’m kind of surprised Jeff agreed with the flowers at all (as you mentioned, his book is very clear on the stuff that “does” things vs. kinds of things we gals like). That book is my Bible now.
Comment from Ann Wesley Hardin
Time January 28, 2009 at 8:27 pm
This is so weird. I’ve had an eerily similar thing going on with a bartender too. The guy slipped me his number one day, I texted him back so he’d have my number, and…he did nothing. No follow through. Nada. Zip.
But I still go in there, we’re still friends, although there’s no more flirting. I don’t know what’s going on in his head and the truth is, I don’t really care. All I know is if he was interested, he’d want that face time out of the bar. End of.
Hope it works out for you though!
Comment from mmagnolia
Time January 28, 2009 at 11:58 pm
All Hearts!
Yep…JMdear’s “Leap before you look” is exquisite advice altho’ canB excruciating2!
Aha! The Girlz Cave today is of 10% self-proclaiming *guys*.
Yipes, GlenDear: This ex”dumb schoolgirl” rates Your text as truetrue+tough!
Origami = cool; maybe t’is MissingLink;
99 Bouquets on the wall…or Bartenders!
Comment from Melissa
Time January 29, 2009 at 11:32 am
I also agree with Seductress…less is definitely waaaaay more.
Do NOT send flowers or a cute card.
Flirt with him in a more DIRECT way, to indicate you are giving him the green light to ask for your number, or ask you out. Men still like the feeling of accomplishment when they pursue you and you are receptive. If he doesn’t get the hint, remember he just might have a girl-friend. (I assume you checked to see if he had a wedding band long ago 
Again, like a dance…he leads, you follow.
All my best,
Melissa
Comment from Eric the BeehiveHairdresser
Time January 29, 2009 at 4:06 pm
I like Jeff’s idea of not making it a secret admirer, and I don’t think that any gift from a gal who I often flirt with would be stalkerish – unless it was a box full of my old cut nails or something.
Also, eight months!!! I hope that all this time the crush hasn’t caused you to cancel out the opportunities for welcoming and getting to know other men.
We only live once and eight months is a loooooong time.
Best of luck with your gift giving.
Comment from Andy
Time February 1, 2009 at 9:39 pm
Anything that means you’ve put a lot of time into it (origami flowers) will totally freak him out (he wouldn’t spend that much time on anyone unless he thinks she’ll say yes to marriage).
Just be upfront – buy him a drink on V day and tell him you like him, ask him if he likes you (without crying or puppy dog eyes) be ready for a yes or a no. Just be straightforward – men, generally, hate the games we feel women make us play: especially in courting. True – he’ll enjoy the chase but after 8 months if you’re not feeling pursued, maybe it’s time to look elsewhere. Do check in with him though – he might THINK he’s pursuing you even if you dont.
Comment from Sassy
Time January 28, 2009 at 8:33 am
I think Jeff’s right on (as usual), and I think I would actually re-think the whole origami flower thing. It’s a little too much for a stud bartender. And he could get a lot of grief from the guys. How about something less showy, like a small, special piece(s) of chocolate? Something that can fit into a pocket, rather than sit on the bar?
Just a thought. Guys don’t want to stick out, especially on V-Day.
Good luck!