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How to approach a shy co-worker in a touchy situation?


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Posted

I have my eye on this girl at work, but since I've only spoken to her one time, I really don't know how to proceed. The one conversation was in the hall many months ago with her and her friend, "Jen". After that conversation, I got the feeling that this was someone I wouldn't mind getting to know better. However, at the time, I was informed that she was married, so I thought that was that. Now I have learned that she is recently divorced, and I would like to talk to her to explore the possibility of hanging out. I am aware that it may be some time before she's comfortable with dating again, but I have the following questions:

 

1. Since I'm sure she doesn't even know my name, and because she is kind of a reserved girl, would I be better talking to "Jen" about this first? I've known "Jen" for almost three years, and though we aren't close friends or anything, it wouldn't be awkward for me to state that I have an interest in her friend.

 

2. If "Jen" and/or you all think it's a good idea to speak to this girl, how exactly do I do it? My office is huge, and she's on the opposite side of it - so it's not like I could stage a "coincidental" meeting at the copy machine, etc. Talking to her will pretty much mean walking over to her office and saying hi - much like many of you remember I did with my last co-worker interest, Rebecca, last Fall. I had help in that situation, something that prepared her for me before I spoke to her. And I'm wondering if talking to "Jen" will prevent me from blindsiding this girl, also.

 

and finally

 

3. If she does seem open to talking to me more, do you agree that doing office things for awhile would be best? By that, I mean getting lunch or going out for a walk during our breaks, etc? I certainly don't want to ask her out too quickly, and that's especially true if she's trying to get over a divorce.

 

I am not shy at all, and have no problem bypassing "Jen", but I really question if talking to this girl straight-on is such a good idea given the touchy situation.

 

As always, thanks for your input.

Posted

you don't even need to talk to "Jen". talk to the girl directly. come up with some B.S. work-related question to break the ice & just get you two talking. that way you'll give her a chance to get used to you & warm up to you. then maybe follow that up w/ something purely social. also, if you have inter-office email, using that could be a good way to get somebody's attention.

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Posted
Originally posted by Nomad

you don't even need to talk to "Jen". talk to the girl directly. come up with some B.S. work-related question to break the ice & just get you two talking. that way you'll give her a chance to get used to you & warm up to you. then maybe follow that up w/ something purely social. also, if you have inter-office email, using that could be a good way to get somebody's attention.

 

That sounds good on paper, but there is no B.S. work-related question I could ask her that would make sense. Anything that I would ask her I could easily ask the folks in my unit. I agree that e-mail is a good way to get someone's attention, but again, what do I say? I am not opposed to writing her a little something, but I fear that anything I send will come off as awkward.

 

I generally agree that speaking to folks directly is the best method, but I want to make sure I handle this carefully.

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Posted

Double post deleted.

Posted

why are you so worked up about just talking to this girl? are you nervous w/ every girl you approach? I'm shy & I think it's great when people reach out to me. Shy people usually WANT to talk, but feel they can't. If there's no work-related question you can ask, then just ask some benign personal question like, "Hey I saw you with a Wendy's bag the other day...is there a Wendy's near our office?" or some bull**** like that.

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Posted
Originally posted by Nomad

why are you so worked up about just talking to this girl? are you nervous w/ every girl you approach? I'm shy & I think it's great when people reach out to me. Shy people usually WANT to talk, but feel they can't. If there's no work-related question you can ask, then just ask some benign personal question like, "Hey I saw you with a Wendy's bag the other day...is there a Wendy's near our office?" or some bull**** like that.

 

I am not shy, nor am I nervous. However, I have been told that this girl is very reserved and I have found that people who like to keep their private lives private generally don't react well to direct interactions. Plus, I don't want to put any pressure on her if she is fresh out of a divorce and dating is the last thing on her mind. That's why I thought running this by her friend to test the waters might not be such a bad idea.

Posted

"Running it by" her friend could work, but it could also backfire in one of 2 ways:

 

1) her friend gets jealous (as girls often do) that a guy's interested in her friend & not in HER, causing her to badmouth you to her friend. ever try to mack on a girl w/ her friend right next to her, rolling her eyes & sh*t? it's not comfortable.

 

2) Jen will tell friend, "Hey, that [your name here] guy likes you &..." this might scare her off hearing immediately that you're interested, even if she's hearing it from Jen. if you approach her more casually first that'll give her time for her to warm up to you, letting you ease into something romantic.

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Posted
Originally posted by Nomad

"Running it by" her friend could work, but it could also backfire in one of 2 ways:

 

1) her friend gets jealous (as girls often do) that a guy's interested in her friend & not in HER, causing her to badmouth you to her friend. ever try to mack on a girl w/ her friend right next to her, rolling her eyes & sh*t? it's not comfortable.

 

2) Jen will tell friend, "Hey, that [your name here] guy likes you &..." this might scare her off hearing immediately that you're interested, even if she's hearing it from Jen. if you approach her more casually first that'll give her time for her to warm up to you, letting you ease into something romantic.

 

Hmmm, good points. Don't have to worry about # 1 - her friend is married. # 2 is a legitimate concern for me. That has happened in the past. I've had the "running it by" thing work before, but it's always a risk.

Posted

Life is short...just go for it. The worst that's gonna happen is the girl says, "No thanks." And look at it this way: if things get awkward, she's all the way on the other side of the office, so you don't have to deal w/ her. Good luck, man.

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Posted

Any other thoughts? I will probably do something sooner rather than later. I'm just thinking...if it were me, I would feel better knowing someone was interested before they actually came over. It wouldn't completely catch me off guard or anything.

Posted

If you work in a huge office and don't run into her much I would just go ahead and ask her to lunch one day. Even if she says no its not like you have to talk to her all the time. Just go for it. What have you really got to lose?

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Posted
Originally posted by Hund1976

What have you really got to lose?

 

Nothing really. So I can ask someone who is essentially a stranger to lunch just like that?

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Posted
Originally posted by WhereSpiritsRoam

Nothing really. So I can ask someone who is essentially a stranger to lunch just like that?

 

What about inviting her and her friend at the same time so it doesn't seem as forward or as obvious?

Posted

Ummmmm... What about just arriving at the same time she does in the morning and 'accidentally' happening to walk into the building at the same time she does? Wouldn't that be a perfect way to strike up a conversation and begin to get to know her if that happened a time or two? Or at lunch time? (Don't accidentally leave at the same time and strike up a conversation as you're leaving, though, because that could be a little scary.)

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Posted
Originally posted by sleeplessindallas

Ummmmm... What about just arriving at the same time she does in the morning and 'accidentally' happening to walk into the building at the same time she does? Wouldn't that be a perfect way to strike up a conversation and begin to get to know her if that happened a time or two? Or at lunch time? (Don't accidentally leave at the same time and strike up a conversation as you're leaving, though, because that could be a little scary.)

 

It's a good idea, sleepless, but it won't work. I don't know what time she gets in, and I suspect it's later than I do, and I'm not going to alter my schedule just to "accidentally" bump into her. Lunchtime might be more feasible, but it would probably be a matter of luck, as my office is huge and I have no idea when she leaves. That's why I thought about inviting both her and her friend out with me sometime - that way I could be guaranteed to see her.

Posted

stop trying do date your co workers. especially this one.

 

going through a divorce is a traumatic thing and work may be the last thing on her mind so she may be trying to concentrate on it more than normal. she does not want a distraction. plus you do not want someone coming out of a trauma. they won't know how they feel about you.

 

meet women somewhere else. dating co workers is not a good policy.

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Posted
Originally posted by prisoner

dating co workers is not a good policy.

 

I generally agree with you, except for large offices such as mine. Meeting people at work is my best opportunity, since it's only a matter of time before I find someone in an office of 400. I am being sensitive about her divorce - as we speak, someone is speaking with her to gauge her feelings about meeting someone new. How I proceed will be based entirely on that feedback.

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Posted

Apparently finding out that someone is interested in her has raised her spirits, which I'm happy about. Hmmm...what to do...what to do???

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Posted

I probably need to get some cajones!

Posted

this is dating not tradecraft.

 

and just because there are alot of people in your office does not make it a safe environment for anyone but you. be careful is too light a phrase for the advice I have.

  • Author
Posted
Originally posted by prisoner

this is dating not tradecraft.

 

and just because there are alot of people in your office does not make it a safe environment for anyone but you. be careful is too light a phrase for the advice I have.

 

I am not exactly a babe magnet. I have to try for folks whenever I get the chance.

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Posted

I may just do something big tomorrow. What the heck? You can't win big if you don't roll the dice.

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Posted

While I want to do something, I know I probably have to tread warily here. But for those of you who know me, treading warily isn't exactly my forte`. I am definitely not going to win any awards for subtlety. How can I talk to and spend time with this girl without coming on too strong? Should I only hang out with her at work for awhile, and if so, for how long?

 

Signed,

Confused and don't want to screw up again

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Posted

This is a major-league BUMP.

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Posted

Another BUMP for the usual weekday crowd.

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