So I've never dated where I work, kind of always had a rule against it, but I've really developed a thing with this one co-worker. I think I'm willing to break the rule this time and pursue a new job if I have to. I have had a relatively unsuccessful dating career to this point so I'm reaching out for advice here.

A little background, I've worked with her for several months but only over the past few weeks have we really developed a bit of a bond. I don't see her everyday, probably 2-3 times a week. Whenever I see her she seems to go out of her way to smile, call me by some pet name, or whatever. IOI or friendly coworker?

We chat on the company instant messaging system everyday about various things, usually work related but we do go off-topic on our lives outside of work occasionally and/or talk about other office gossip. She teases and jokes with me all the time and I reciprocate.

She used to always tell me how I could never leave the company because I was too good, now she's telling me I should move onto another company because I am too good(I could make more $ elsewhere). Possibly she wants to date me but not if we are coworkers? I'm not sure.

On facebook there was some thread where I ended up suggesting if she does x I'll do y with her. She liked this(IOI?). Again this is facebook, I don't know if I should read anything into that...

I tried to get her out of the office for a drink a week ago but it didn't pan out because she had other plans. Now she did hint at doing it in the future, but we never got anything set in stone(we were both extremely busy with work stuff all this week) and the problem with this is, she was going to invite some other people as well.

Does she have any interest in me or am I screwing with my emotions over this situation? If she does have interest, any suggestions on how I can get her out of the office?

I think she does but perhaps act on it before the spark fades.

I had a similar scenario and we were hitting it off until i gave
Up n lost confidence n now we dont even talk.

As for her wantimg to bring some friends. That sounds normal
Dude, she probably doesnt want the akwardnesa being alone with u
Or shes just nervous. Go out wit her n her friends

want to get with a co-worker at work but don't want to risk losing your job? no problem, this will be addressed later in the post

does she have interest?, not important, could be friendly, could be interest, what is important is that you have interest, and you are sure of that

so, what's going on here?, she is not giving you a clear view of her intent

how to fix this? make your intent more clear, so she is forced to clarify her intent

how do you accomplish that? just be honest with her, and narrow it down, make things more specific, let her know you find her attractive and would like to take her out on a date if she is available (this is you leading, she doesn't have to think long and hard, just either give you a yes or a no)

if she has excuses, cut through them, once again be very clear in your intentions towards her, don't leave this up to ''im going to be aloof and flirt with her at the risk of losing my job if she isn't interested just because I don't approach often and right now this feels like the only thing I have going on''

so for example, if she says yes, followed by blah blah blah, im busy for reason XYZ, you say, well when are you free?, she gives you an answer, ask her if she is sure she will be able to make it that day with no other problems?, if she is wishy washy and can't give you a yes, ask her when she will be free on a day where it wouldn't be possible that something else comes up? (if she wants to know why, tell the truth, you don't like to clear your plans for other plans that may fall through)

that is all, she either wants to go on a date with you (you should call it that btw, don't say ''hang out'' or ''grab a drink'' or ''get a coffee'' in this situation, say ''date'') or she doesn't want to, if not, you have your answer, she is not interested and it is that simple, and if she agrees and meets you without problems, make sure to try to at least kiss her on your date and have a good time

doing this will save you a huge headache, as long as it is formal there is no way that this can be mis-interpreted as sexual harassment (unless you persist after she clearly shows dis-interest), you will know where you stand, and this has been field tested

GOOD LUCK

Thank you, this is very sound advice. I got her phone number today but I didn't give her any clue as to my intentions, I just asked for it and she gave it to me. I will be trying your direct approach over the phone in a few days. It's pretty much impossible to get her alone at work and I don't want to put either of us in an awkward position, especially her.

I'm still not sure about the signals she's been throwing around though... when I asked for her number today I think I might of caught her off guard, she seemed surprised maybe? She gave it to me immediately though.

Do you or anyone else have anymore insight as far as how I should handle the phone call?

Thanks again.

I find "social inertia" is always the overriding factor. If you've been just coworkers with someone for a long time, it's hard to change that. Same if she's your best friend's girl, or your girl's best friend, or any other scenario where she'd be off limits. Sure, in the early stages there would be interest. But rarely does that interest last for very long. And even then, when you finally find the guts to make a move, it just feels so weird, because you've been something else to her for so long.

A lot of the time you need a catalyst. An afterwork party with a lot of drinks. A change in circumstances where you no longer work there. Something like that. And even then, you gotta be smooth and discrete.

But if you're okay with the strong possibility of rejection, you could just go for it like you would any other girl you met at a bar.

don't avoid awkwardness, the more social pressure that is placed on the situation the better, it will allow you to demonstrate more confidence in the face of fear, don't ask her out over the phone, ask her out in person, go after her emotions not her logic, be ok with what happens and be proud of yourself for manning up, if she is not interested it won't be awkward unless you precieve it that way, girls get asked out all the time, it's not a big deal

So I was planning to talk to her today but she wasn't available. I'll attempt to again tomorrow. Any advice if she brings up the fact that we are co-workers and being worried about the potential consequences?

Pumpington already covered everything but I'm not sure if you thought about what he wrote... Are you interested in this girl because you think she has interest in you?

You started off by stating that your dating history isn't all that great. ^This dynamic might have something to do with it.
Always leave the girl a gracious "way out". By this, I don't mean for you to simply give up the moment a girl becomes a bit skittish but in this particular situation, you two already have a strong working relationship. No matter what guys say, they usually feel a little sting from a rejection and girls know this. Chaotic chicks love handing out the sting simply for their own amusement. Level headed women on the other hand will frame their rejections better . . . in a way that can be digested by the guy without chopping his psychological balls off. Look, if she's into you, she's into you. A girl will make it work even risking a professional career.

Just tell her, "I'm, willing to risk it to give 'us' a try." - If she states that she's not willing to do the same, let it go and tell her you respect her professionalism.

This is a pick up forum, not a "how to score on a girl that likes me" forum. Invest into your future love life by reading through some of the threads that pertain to open, routine, and close. (Yeah, how to secure a relationship with girls that interest you, regardless of who they are, how you met them, and your standing relationship with them.)

understood, thanks everyone.