Romantic dilemma: you make the call

In My Humble Opinion
1

I’ll call her Isabel. She’s a barista at my regular Starbucks. And, in fact, she’s the only reason I have a regular Starbucks: I’ve got a thing for her. There’s no lurid backstory or tragic narrative: we are acquainted, but I don’t know her, and she doesn’t know me. We’ve been introduced a few times by a good friend of mine, Jacob, who happens to be her manager. Infatuation, plain and simple.

Lately Isabel has been going through a particularly difficult time, in the midst of a rather nasty divorce, with custody battles, the whole bit. A brief, unsteady marriage after a long, tortured relationship. There are problems at work, now, too, Jacob tells me. Trouble afoot at the local 'bucks. She had a car accident last week. Things just seem to keep getting worse, and it’s all taking quite a toll on Isabel.

Yet, somehow, we are not deterred. Assuming for the moment that we could muster the courage and invent the context to ask her out, the problem is that this could put Jacob in a very difficult position, or (perish the thought) Isabel in a very uncomfortable position…when of course it is only comfort we would wish to provide. At least in the short term, it’s problematic.

Yet our heart goes out to her. We…that is, I (sorry, been watching Elizabeth I) thought, I’ll send her flowers. Not roses. Anonymously. Or maybe with a note and a bit of verse (I know, I know…sickening, isn’t it? I should have put “TMI” in the thread title). Just some small counterpoint to the absolutely godawful time she’s been having.

The theory here being: flowers from secret admirer = pleasantly mysterious; flowers from tall skinny latte man who’s friends with your boss and whom you barely know = creepy. But maybe they’re both creepy…it’s hard to know, I’ve never gotten flowers (or sent them, apparently). Or maybe it’s sweet but just cowardly? Or even dishonest? Immature? Should I just damn the torpedoes and ask her out? Or mind my own business, since I really only know what I know secondhand, and she’s got enough trouble at the moment. But, I mean, it’s just flowers, innit? Overthinking the simple things = priceless :slight_smile:

2

You could always ask her out for coffee. :wink:

This is the only thing that would give me pause. Even if you preface your speech with, “I know it’s none of my business, but I heard you were having tough times and I thought this would cheer you up…” it still means that people have been telling other people her business. Depending on how she guards her privacy and her mood, this could be trouble for you.

Otherwise, I think it’s thoughtful of you to woo her this way. She may not be eager to add something else to her plate right now, but I wish you luck.

3

Lay your cards on the table by giving her options without pressure: indicate your general affection and interest, indicate that you understand that her plates are full right now, but that if and when she is available/looking, that you’d like an application (for her, not for Starbucks).

Don’t try too hard, don’t press.

4

Cerberus, you’re a genius. Ask her for an application. Fill it out as if you were applying for her. Give it to her and see what he says. Fake confusion- “Oh, that’s for a job? Oh, no, I meant an application to date you.” She’ll think it’s totally cute and original. That’s all it takes.

5

I have done this and it did not work, but that’s just me.

My two cents is that while someone who is going through all the unpleasant stuff you’ve mentioned can really use some good friends by her side, it’s not the right time to try starting a relationship with her. That sounds like it has “train wreck” written all over it.

6

It sounds like she’s an adult, though. This sounds a bit more appealing to a teenage demographic.

I’m with Valgard. If she’s having such a rough time of it, don’t impose, and particularly not in her place of work. She’s got nowhere to escape from you if she finds you odious. (Not that you are – you get what I mean.)

7

It’s all in the way you play it. You’re not supposed to act like a child/dope. You act your age, of course! It doesn’t matter how old they are, it’s still cute.

8

I agree on this one. However, as someone who has had someone do something totally unexpected during a personal crisis, I say buy her flowers and tell her that they’re just to brighten her day. Don’t explain, just smile and say “Have a nice day.” No strings attached, not romantic, just because girls like pretty things and she sounds like she could use something pretty in her life. Let her know, through actions, that someone hopes she’s having a good day.

~Tasha

9

40 year old married guy who never had much luck dating checking in, but I wouldn’t mention too much about her personal life, it comes off stalkerish. Also, it would kind of skeeve me out if someone was talking to my boss about me.

Can’t you just ask her out for drink after work?

10

Another vote for Valgard here. I came in to post exactly this.
Also, an even worse case to this scenario is that she accepts your advances under the midst of this traumatic time in her life. Then later after the smoke clears she realizes that she’s not that in to you.

Now, YOU"VE entered a world of heartbreak.

It sounds callous but you generally don’t want to get involved with a person who has a bunch of emotional garbage. They need to sort that stuff out (with friends or what have you) BEFORE they get in a relationship. (YMMV)

11

Could you possibly give your card to her manager, Jacob, and have him give it to her and say this guy would like you to call him if you’re interested? If she’s interested, she’ll call; if she isn’t in a new relationship place, or (unfortunately) not interested in you, she won’t. No pressure on any front.

Or just ask her out for a drink after work.

12

I was going to say this gave off a creepy “asking the manager’s permission to date one of his employees” vibe, but on re-reading the OP it sounds as if they’re all talking on quite friendly terms already, so scratch that. The OP would need to make sure she knows whose business card it is, and not just some random guy’s!

13

Agree with this.

Now isn’t the right time to try to start a relationship with her – but to let her know that you wanted to make her smile – that’s enough.

14

I like this idea the best of the suggestions made so far. Since for all you know she may be acting friendly with you just because it’s part of her job (who wouldn’t try to be friendly to their boss’s pal?), I think it’s best to try to be friendly and low-key until you get more indication from her that she really wants something more. I’d just give them to her rather than going the “secret admirer” route, which I do think has a risk of seeming like a stalker thing.
Good luck to you. :slight_smile:

15

I just want to third the “low key flowers” approach. Make sure it’s a small bouquet of relatively inexpensive flowers (daisys or the like). NO ROSES! And just be cool when you give them to her. Then, let it be. This will accomplish 2 things: first, it will brighten her day. Second, when she is feeling ready for a romantic type relationship, you will have one foot in the door. Let her make the next move though. If she continues to act merely professionally courteous, then follow her lead. Either she isn’t interested, or it just isn’t the right time. But if she begins to act more friendly, you’ll know she liked it and you can begin to (gently) take it further.

Right now probably isn’t the time to begin something with her, but it could very well be he right time to put a big star over your head that says “This Guy Is Sweet!!” which will be great for you when she is ready to date.

Good luck!
(p.s. don’t do the flowers anonymously, you want the “credit” for this)

16

I wouldn’t do anything. No flowers, no card, nothing. Given your current (non-) relationship with her, flowers are far more likely to send the message that you want to start dating and/or are a creepy admirer than make her happy. I think you’re right not to try to start dating her at this point, and if you make any gestures that can be perceived as romantic overtures, you’re going to kill your chances to date in the future.

Be friendly when you see her, give her conversational openings to chat about more than coffee if she has time and wants to, but otherwise be low pressure. When you sense she might be up for it, ask her out. Don’t make a big deal out of it (no flowers), just ask. Don’t indicate that you have any knowledge about her personal life that she herself hasn’t given you.

17

As someone who has done this very thing, my advice to you is… Don’t. You’ll come across as a fool.

Give her a nice little gift, in person. Smaller than flowers, but meaningful. Or just be friendly and be the high point of her days.

18

Former Barista:

If you actualy order “skinny” lattes, she thinks you’re gay.

19

Couldn’t agree more. Flowers would be OK if she weren’t essentially a prisoner in a cage who will be forced to react to you and in some sense answer you for the flowers the next time she sees you. That’s the problem: if she’s really not interested, she can’t possibly just avoid you unless she leaves the job. Whether you want to or not, you’re putting her in a bit of a tough position by giving her flowers. She’s got nowhere to hide, if that’s what she feels like doing.

A lot depends on her personality, of course. I’m just thinking of my own reaction. I’m stuck behind the counter, someone comes in and declares their love (and that’s what you’re doing, whatever the type of flowers, and however low-key you try to make it), and now I know they’re going to come back, and I know I have to say something, and deal with the person, and I really just don’t want to. But as I say, that’s me. Maybe she’s different.

Giraffe’s strategy seems much more likely to work.

20

:smiley: Drink names have been changed to protect the innocent (former Barista, here, too).

Well I’m not sure what to do, but I am glad I asked. I like tashabot’s suggestion, which was probably closest to what I had in mind to begin with. It’s not meant to be a romantic overture, but, as Giraffe points out, it can’t really help but be interpreted that way.

I’ve ruled out just asking her out because, as explained, it’s really the wrong time, plus it doesn’t really fall under the category of doing something nice for someone, if I’m asking her to make some decision about me. I didn’t want it to be about me at all (as much as I’d love that gold star, I don’t really need the credit), really, but perhaps it’s folly to pretend that as well.

Agreed that I should rule out anonymity being any part of it. I can’t really say what’s wrong with it, but it strikes me as less than honest in some way, and it sounds like most of you feel uneasy about it, too.

The beauty of Giraffe’s suggestion is that it requires no effort on my part and won’t get me into trouble. As conducive to my lifestyle as that is, it leaves something to be desired here.

Keep in mind that we don’t see eachother often, and I don’t really need to be going to $tarbucks anyway (especially these days), so if it makes a difference, I could just make the gesture and then make myself scarce for a few months.

Or maybe a different gift, something small and less…loaded with meaning?

Or maybe nothing at all; no good deed goes unpunished, they say. It seems cynical but maybe it’s true. I’d hate to think that by doing this I’m only going to make myself feel better…