Spoilers: just ask her out
December 11, 2011 9:04 AM   Subscribe

I'm interested in a girl at work, it's of course a bit complicated, unsure how to proceed and/or need a push forward.

There's a girl at work (Stephanie!) who reports to a good friend of mine. A few weeks ago, they either fooled around or came darn close (either way, 99% sure there is nothing ongoing or since.)

I've grown to be friends with Stephanie even outside work, only to find she's pretty awesome and I'd like to ask her out. Problem is I have no idea how to gauge whether she'd be interested, how to move to that from friendship or if friendship is salvageable if i ask and she says no, or for that matter if she is still attracted to my friend. He might still be into her, too.

I am also friends with her best friend, and have considered asking her. I think she'd answer in confidence if I asked, but I obviously can't be sure and I don't know if that's really reasonable.

In any case, I'm concerned if I don't act on this somehow I might fall into stereotypical Internet Nice Guy™ behavior, so please help me pick a course of action!

Options so far:
1. Just ask her out and come what may
2. Flirt with her and see how she reacts (not sure how smoothly I can pull this one off, since it involves moving from simple friendship and I'm not the best flirt anyway)
2. Ask her friend
3. Steer clear
4. ?

Throwaway email (some colleagues do read mefi): mefirela@hushmail.com

Fake edit: Yeah, when I got to the title I had to write that. If you vote 1, please include some advice on saving the friendships involved if it goes south - there's a whole social circle there.
posted by anonymous to Human Relations (16 answers total) 3 users marked this as a favorite
 
I am guessing you're young, and I hope the two of you are working in a restaurant or call center or some other high-churn, fungible job right now.

Because if not, and if you're actually working in a long-term career-relevant place, listen: workplace romances are bad, bad, bad on about nine different levels. So unless there's an overwhelming and undeniable mutual attraction that is much bigger than either of you can contain -- and it sure doesn't sound that way here -- there are four billion other Stephanies out there, and you'll be a lot better off eating where you don't shit.

(Or shitting where you don't eat, or however that expression works.)
posted by rokusan at 9:14 AM on December 11, 2011 [7 favorites]


Just came here to nth what rokusan said. If this is a Capital-C Career job, look for romance elsewhere. Even if it's not, consider that the economy is kind of in the crapper and shooting yourself in the foot with workplace drama at your current (existing) job might be a shortcut towards losing it, which could be hard to recover from. I'd go with 3, steer clear. Sign up for okcupid. It'll be a boatload of drama too, but hopefully it'll be compartmentalized drama that won't screw with your job.
posted by Alterscape at 9:18 AM on December 11, 2011 [1 favorite]


Nothing more to say except to agree. Stop while you still can! I am the Ghost of Christmas Future!
posted by the jam at 9:36 AM on December 11, 2011 [2 favorites]


Disagree, sorta. If you're young, now is the time to make fun mistakes like this. Especially if its a relatively shit job that you can find a replacement for.
posted by softlord at 9:40 AM on December 11, 2011


Er...to answer your actual question: Ask her out to something specific, make it clear that it'd be a date (do you want a relationship? or just to fool around? probably good to be sure of your intent, too), also make it clear that it'd be totally fine if she doesn't want to (so she doesn't feel backed into a corner and says yes because she doesn't want things to be awkward at work after).

Be safe and have fun!
posted by softlord at 9:43 AM on December 11, 2011


I'm not as averse to dating at work as some people here are, but it is a factor. I think her interest in your friend is a bigger factor.

But look, it's not good to be pining away wanting more. Maybe you should do this. If you do, ask her on a date using the word date. If she says no, big deal, you're both grown ups and it doesn't need to cause awkwardness.
posted by J. Wilson at 9:43 AM on December 11, 2011


She works in the same place as you. If the job matters, don't do it.

Another friend of yours may be involved in some way. If there is a possible repercussion from attempting to ask her out, don't do it.

You don't know how she'll react. If a bad reaction could affect your job or other friendship, don't do it.

Bear in mind you may already have been 'friended', in which case you are out of the running.

Ask her friend, if there is a negative repercussion, it is limited, will probably not get around, and is probably of lesser impact than being rebuffed by your 'flame' directly.
posted by epo at 10:06 AM on December 11, 2011 [1 favorite]


I've met a few boyfriends at work (both in service and Career jobs). Most of the time, bad outcomes were averted by one or both of us leaving before the relationship ended. However, one ended while we were still colleagues and it was the WORST break-up in my life. The agony and drama of working with an ex lasted way longer than the actual relationship itself (which was a two/three month thing). And that was an amicable break-up--the problem was that we had to see each other every day and there was no way to have a healthy period of no-contact. It got pretty awful.

I'm not saying it has to end horribly, but be aware of how very awkward even a fling can make things. I say maybe ask her out to something friendly and innocuous just to get to know her a bit and see if there is chemistry. I would also avoid flirting at work because it could easily make her uncomfortable even if she likes you. Tread carefully and slowly. If things work out, agree to keep work and personal stuff as separate as possible, and please DO NOT tell anyone (except maybe HR if you have to) that you are dating until things are serious and difficult to conceal (like at more relaxed work functions).

Honestly though, I think the weirdest thing is that she almost (or did?) fool around with your friend, whom she also reports to. Putting you into the mix might be a little...much, but it's not impossible, especially if you're all fairly young. Good luck!
posted by swingbraid at 3:29 PM on December 11, 2011 [1 favorite]


Leaving all the work stuff aside, I actually would ask her best friend for advice -- she knows the situation better than we do, and if Stephanie is secretly into you also, the friend is probably aware of this. At the very least, she ought to be able to give you some guidance.

I know this can feel kind of 3rd grade, but I seriously think 50% of relationships -- especially between people who are still kind of young -- happen in part thanks to a Kind Mutual Friend who helps things along. See what the Friend thinks.
posted by Countess Sandwich at 3:40 PM on December 11, 2011


In general, I think it's not a great idea; I've done it, and what salvaged the situation was that the dating was brief and we didn't work together, and didn't run in the same circles. If you work side by side and it doesn't work out, it's going to be a problem. The fact that you are friends who are in the same social circle is a problem. Also, the fact that she has hooked up with or may be into your friend (who I assume is in the same social circle) is a problem. An even bigger problem is that your friend is the superior of at least one of you, and you don't know how he feels about her, or how he'd feel about you trying to date her.

So to sum up, this sounds like a horrible idea but if you are determine to do it, what you probably should be doing is talking to both HER friend (first, to know if there's interest) and YOUR friend (second, to see if there'd be fallout) and getting some facts or impressions before you proceed any farther.
posted by sm1tten at 4:29 PM on December 11, 2011


I don't go after people my friends have hooked up with--there's always someone else out there and the karma potential is bad. The fact that I have feelings for someone doesn't mean I need pursue them.
posted by Ironmouth at 6:40 PM on December 11, 2011 [2 favorites]


Forgive me for being crass, but I think you shouldn't shit where you eat.
posted by easy, lucky, free at 11:28 PM on December 11, 2011


I'm going to be a bit contrary here. I work in a large organisation (>600 people) and can count probably somewhere over 10 relationships that have started between people here. Some of them are now married, some are long term partnered, some have broken up, some no longer work here, some were never more than faintly titillating one night stands that somehow we heard about, etc. I can't think of any that have crashed and burned too badly for anyone.

So maybe consider the risks, go in with your eyes open and see what happens.
posted by deadwax at 11:42 PM on December 11, 2011


1- Ask her out in a way allows both of you to walk away happy no matter what the answer is. Don't wait so long that you get into the thing of where you get invested in her saying yes, and you get inappropriately bummed or angry if she isn't interested. Don't do that thing where you organize work outings as cover for trying to pretend-date her, it creeps people out. Just be casual and upfront about it. When friendships go bad because one wants to date the other, it's almost always because the asker did it the wrong way.

2- Workplace relationships go badly when one or both of the parties don't compartmentalize properly. It is an absolute must! Work stuff is work stuff, and relationship stuff is separate.

3- Workplace breakups seem to go badly when people don't break up the right way, where things are left unresolved. If you ever have to do this, always make sure you have that covered. If anger and resentment start to even have a glimmer of appearance, sit down and talk it out.

4- Ironmouth makes a good point.
posted by gjc at 6:53 AM on December 12, 2011


If this is a Career job - you can also wreck other lives. Staffing projects around known couples is a nightmare and I certainly do not enjoy having a getting a spot filled by a person whose options are limited not by skill or travel pref, but by a requirement that they not be staffed on a project with or involved with their other half. A couple in the workforce makes merit take a backseat to compliance. That's outside of all the drama if it doesn't workout.
posted by Lesser Shrew at 9:50 AM on December 12, 2011


My husband and I met at work. Why I think it turned out ok:
- Completely seperate departments, never actually worked with each other
- Completely seperate bosses who were just some random guys as far as we were concerned.
- Hardly anybody knew we were dating except for extremely close work friends, none of whom either of us ever fooled around with

Just the fact that she fooled around with your friend who is her boss makes this a possibly toxic no-go zone. Sorry so my vote is for #3 until either of you leave your job. And even then, preferably when she leaves the job because if you leave, she'll still be reporting to your good friend.

The world is big, go live in it.
posted by like_neon at 4:46 AM on December 13, 2011


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