Don’t look at it so negatively. It’s not that you shouldn’t do nice things for people. It’s that you need to have the right kind of relationship with someone for the nice gesture to accomplish the goal (making them happy) without any unpleasant side effects (creeping them out).
If you were friends with this girl and never wanted to take it further, getting her a gift or flowers or something at a rough patch in her life would be lovely. Or, if you were acquaintances and circumstances were such that you were both available for whatever might follow, that would be a cool way to indicate you like her and want her to be happy.
Your ideas for a gesture are very thoughtful. You’re just not the right person in her life to carry them out right now.
You asked, I will offer my opinion. Flowers from some secret admirer during nasty divorce proceedings = exceedingly creepy and possible attempt by soon-to-be-ex to discredit. Flowers from skinny latte guy who is friends with your boss with a note that says “looked like you could use a pick-me-up” = sweet gesture likely to get special attention (and depending on skinny latte guy’s personality/looks, a date).
Honestly, though – flowers from a stranger-ish guy are usually creepy. I would recommend going with a “hey, wanna go out for ice cream sometime? You look like you could use some fun right about now.”
I think you should be completely honest and straightforward just tell her what you think, not what you think she wants to hear.
You need not necessarily be utterly forthcoming though - no need to go way over the top and tell her your plans for the next thirty years of your lives together, but you could, I dunno, tell her you like her.
I don’t think anonymous flowers are a good idea at all. I’m not sure that non-anonymous gifts are a great idea either, at this stage.
I honestly don’t see the harm in asking her out - sure, she’s got a lot on her plate right now, but a)you’re not supposed to know all about that, are you? and b)it lets her know you’re interested - she can always say “I’ve got a lot on my plate right now”, and you can smile, nod and sensitively understand. What harm could that do?
[ol]
[li]Using your left hand, make a circle with your thumb and forefinger. Keep it ready at your side.[/li][li]With your right hand, point at her. Then point at your chest.[/li][li]Finally, rapidly and repeatedly insert your right index finger into the circle you made with your left hand in step 1.[/li][/ol]
But he DOES know about the problems she’s having and that this is probably not the ideal time to be complicating her life.
Look at it from the lady’s point of view - she’s going through a divorce (stressful), with children involved (more stress). She’s not at the highest paying job in the world. Her #1 priority right now absolutely must be looking out for herself and her kids. Now some guy who has ordered a few coffees from her and who is a friend of her boss says that he’d like to date her.
Sequent may be the most stand-up guy in the world but this is really the wrong thing to drop on her at the wrong time. Even with the best of intentions and the best approach he may be adding a ton of stress to her life when she least needs it, and that’s the harm that it could do.
Maybe telling the person “Hey, you look a little stressed lately” and getting them something innocent like a Dancing Hamster that sings “Don’t worry be happy” that you found on sale at the corner store for $5 would be OK (I’m winging it here, that was the silliest thing I could think of) but anything that smacks of romance (like roses, a date, etc) doesn’t seem like the right thing, IMHO.
Please read this again. You’re a close enough friend of her boss that he’s told you a ton of her personal business. What if she feels (no matter what you intend) like she’s possibly jeopardizing her job if she doesn’t go out with you?
Do you really want to put her in that position at this time in her life?
I have to go with Giraffe and say leave her alone for now. Just be a normal friendly guy.
“Isabel, wait! Come back! It was a joke…I…I…I don’t even know what that means! I love you! No, don’t go! I want you to be my wide receiver and take it in the end zone!”
Hmmm… she knows that you’re friends with her boss, Jacob, right? She knows you’re a regular, right? How about you simply go up to her and say something along the lines of, “I understand that things have been a little rough recently; I’d just like you to know that you never fail to brighten my day.”
For all the reasons mentioned by other posters, if you are going to do something, this is probably the best approach. No biggie, low-key, no reference to knowing her situation, simply an observation and a casual “wanna hang out?”
Gets my vote. Now - while you are out for ice cream, then I gotta go with the black rabbit approach. I also recommend that you make a V for Victory sign and stick your tongue between your fingers - it’s a universal sign of empathy when you see someone who is down - so I hear…
One of my fundamental rules of life is “Never hit on someone who can’t run away screaming.”
She is being paid to be nice to you. Do not forget that. It is her job to make your visit pleasant.
However, if SHE wants to modify that relationship, I would leave it up to her. No matter what you do, if she isn’t interested, it will be awkward and you might have to start drinking real (Dunkin’ Donuts) coffee.
If she’s old enough to not crap her pants, she probably realizes that you are interested in her. That sort of thing really isn’t as subtle as you’d think.
That being said, if you and her boss are in a social situation or “non-work” related situation, suggesting a get together is a safer bet. But be aware of the “Oh crap, I have to date this guy because he is my bosses friend.” dynamic.
Gotta agree with Mangetout on this one. IME, women appreciate honesty and directness in these matters. There’s nothing wrong with just saying, in a non-threatening way, “Hey, I like you, I’d like to take you out on a date sometime, no pressure, just let me know later if you’d like to.” She’s a big girl; if now isn’t the right time in her life, she’ll tell you that. No harm no foul. If you beat around the bush forever, either she’ll get tired of waiting and lose interest in you, or some other dude will ask her out first.
Oh I think not, Auntbeast. Things would have to get a sight worse before that becomes an option. But, alas, I reluctantly have to agree: it’s a good rule. It has the Dread Ring of Truth. Damnit.
Well, I guess the simplest solution is the best one, at least until I know more, or feel more certain about the situation. Wait for the right moment, instead of trying to create it, and maybe then the unadorned truth won’t seem so scary. Thanks, all
You’re good. This almost exactly what I was going to suggest, but maybe something like “You looked a little down yesterday” to go with it. Either statement might work.
I’m not sure I’ll do a good job explaining it, but there’s a big difference between a flower and flowers. They send totally different messages, somehow. A flower is thoughtful and seems much more spontaneous. It’s nice to know a guy you’ve had a casual acquaintanceship noticed you were blue, remembered the next day, and had the impulse to make you smile. Flowers imply more time thinking about you, which could be nice or it could be creepy.
In my limited experience with them anonymous flowers are sweet, but puzzling. If you’re not willing to own up to sending them, you won’t get anywhere with the girl. Not being a mind-reader, she’ll probably never figure out who they’re from. IF you are just eager to cheer her up, being puzzled probably won’t out-weigh the pleasure she’ll get from knowing that someone cares. You’d have to be one of those people who is nice simply for niceness’ sake. They exist, don’t they?
