How to ask a female colleague to spend time with me?

Question

Background

I met this colleague (let's call her Alice) at my new job that I started recently. We work in different teams, so I don't get to meet Alice every day, although I do see her in the corridor or the pantry during breaks. I usually smile at her and greet her. But I never had the opportunity to have a conversation with her since she would be out with her colleagues or on the phone and I wouldn't want to interrupt.

I have noticed that she tends to not talk very much with her male colleagues in the office unless spoken to, and hangs out with her female colleagues most of the time. She is not comfortable acknowledging me when she is with other people, so I don't greet her when she is with people or when I am around people myself.

The timings of our break from office work are quite different, hence I am not able to talk to her consistently. I don't want to coincide my break timings with Alice's, as that is not something I am comfortable doing and would make my intentions blatantly obvious.

I am in India.

Question

I am interested in asking her out eventually, but before I do that I would like to get to know her a little bit (find out if she is taken :) ) and warm her up to me. I may have to go to her work station to ask her, which brings me to my question.

How can I ask Alice to spend time with me?

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Would like to point out that I want to keep this interaction between us completely casual, so she wouldn't think much of it.

I have had prior interactions with Alice, but they were very short greetings with a "How are you?", since we pass each other in the corridor. I just would like to invite her to have a longer conversation with me.

I would like to clarify that I am not trying to ask her out after these short interactions previously mentioned, because I fully well know the outcome and I am aware it's completely inappropriate.

What I am trying to get at is how I can have longer interactions with Alice at work, where it is harder to approach people. Also, only if I feel that we share common interests will I proceed to ask her out.

Answer 1

Simply wait. At some point your work might give you an opportunity to get in contact with her. Maybe a project where you have to work with her or a company party or anything like that. There is also always a chance that you happen to make coffee at the same time and no one else is around and some silly conversation starts up. Perhaps, you do have a little leverage in making something like that happen - by choosing the projects you work on, what role you fill in or simply when you take your break, but don't let this influence important decisions about your professional career.

As long as no natural opportunity arises and she doesn't overtly flirt with you (i.e. smiles and/or greets encouragingly whenever you see each other very clearly) there is no appropriate way to start some private or even intimate talk. Be patient and wait if something happens. And if an opportunity - say at the break - arises, take things slowly.

Most importantly be prepared for the case that nothing ever happens.

While in other locations you can dive into a somewhat risky approach to get to know other people and try to inject yourself into their group, the work place is totally the wrong place for such experiments. You cannot easily leave if you embarass yourself (nor can she simply avoid you) and things can get awkward and affect your and her life pretty badly.

As an encouragement after all this discouragement, most (long-term) relationships are established at school or university, secondmost at work*. But in the latter case, it takes time, and it might not be her.

*according to a study I read a while ago, which was conducted in a western country. For the secondmost place the work place was rivaled by online dating, which was argued by the study authors to overtake the workplace in the near future.

Answer 2

Its a long process. First, identify her's along time and where she will be. And try to talk to her with very common question or comments, as both of you had short greeting. Find some common interest. Like talk about lunch if both of you take lunch from same source. Or it may be about a office activity.

After these kind of question for 1month (approx), you may ask talk something about her. Like, what she will do in this Durga puja or where does she live?

Try to impress her. If all goes right, then you can ask her out. But remember its a long time process.

Answer 3

Although there's already a chosen answer, I would like to throw in my two cents.

I'd suggest the same tecnique I suggested to a question similar to yours: have a light-hearted party were you invite a couple of colleagues thus legitimately enabling you to invite her too.

If she agrees to come, it might be a starting point.

Answer 4

What I have sometimes done when a woman doesn't want to talk to me is to talk to her friends, particularly "women" friends, instead.

From the sound of it, this woman declines to make judgments about you (or other men) on her own, and is highly influenced by her reference points, parents and friends. The latter could make and certainly can break you. Your hope is that her friends will give her "good reports" on you, making it more likely that she will want to talk to you on her own.

More to the point, by talking to her woman friends, you may find a suitable replacement for her from the same "demographic." And if this doesn't work, maybe it's a sign you're in the wrong demographic.

I am reminded of a story of a woman who spent a year "strutting her stuff" before a man's friends, while scrupulously avoiding the man himself (directly). At the end of the year, she did not get the (original) man, but had won the interest of several of his friends, allowing her to pick and choose among them.

Note: There are some critical comments below on an earlier version of this answer. This is the new, improved answer.