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male
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*1234X
writes: Six months ago my office hired a new administrative assistant. She is very beautiful and we hit it off great. As we got to know each other, I realized she was not just a pretty face, but that she had a great personality too. We talk on the phone and go out for drinks pretty often, but she has a boyfriend. She hints that things aren't going to well with him, but she still hasen't broken up with him. About a week ago, we went out for drinks and ended up making out. The next day, it was a little weird, mostly because she didn't want anyone at work to find out. She said the fact that we kissed took her by suprise. Since then, things have gotten back to normal, but I would like more. I have asked her out casually a couple times since last week, but she has had some reason she can't go out. I'm at the point now where I really want to make something happen, but I'm not sure what do to. Do I confess how I'm feeling for her in hopes that she will leave her boyfriend and explore possibilities with me? or, do I continue to play the flirting game and see where it takes us? Oh, and there's one more problem complicating the situation... not only do I have to work with her, but she just got promoted and we have to share an office! Help!!!
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reader, X1234X +, writes (2 August 2005):
Wow...I didn't think I would get such useful advice. Thanks! I think the more I thought about it, the more I realized that it doesn't make sense to poor my heart out, because if it's something she really wants then it will work itself out. So here's my follow up question: Do I continue to flirt and pursue her, or do I step back, try to move on, and cope with the fact that it might not be meant to be?
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reader, becky05 +, writes (1 August 2005):
The reason she cant go out is that she has a boyfriend!
I dont think it would be wise of you to take things any further for a fwe reasons 1) she is in a relationship. 2)She hasnt given you any signs that she is interested in you and 3) you work together.
I think it would be better for both of you if you found someone available.
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female
reader, Anastasia  +, writes (31 July 2005):
 Okay let's see what we have. Girl has boyfriend but flirts with co worker. Made out with co worker while she still has boyfriend. Kind of awkward situation now at work.
Are you sure you want this girl in your life. Infatuation it is I think. She has a boyfriend and even though she says it is not working out the way she wants it too...she is still there..that should say something. I think she is using you as an escape. Guard your heart and your feelings bro. Talking as a woman ...I think this girl is somewhat fickle and needs to make up her mind. And even is she hooks up with you...what are the possibilities that someone else won't catch her eye and you end up being
" the boyfriend who things are not working out well with" Food for thought amigo...good luck ana
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A
female
reader, Bev Conolly  +, writes (31 July 2005):
 Try to stay realistic: you can't "make" something happen. You know that, right? She's either interested - in which case it becomes a mutual decision - or she's not, in which case you do your best to accept that it's not going to happen.
If you mean that you want to make a declaration to her and hope that it pushes her into deciding to dump her boyfriend, you should also be exploring all the possible responses and estimate the likelihood of getting the one you desire.
Presumably, you want to tell her that you want her more than anything and then hear her say, "Oh, me too! I'll just break up with my boyfriend tonight - he really won't mind - so that we can begin our life together!"
Is that the most likely outcome?
Maybe the wording isn't exactly how it goes, but there's a good chance it's something similar. Now you have to ask how reasonable expecting that response is, and consider what other, less pleasing permutations might arise.
Don't forget all the (truthful!) warnings you've heard about workplace relationships, too. Even if you eventually get together, if things should ever break down between you, you're going to be stuck working in the same office with an "ex" every day of the week! Speaking from experience, that can be awkward, at best.
I'd say that you should play it cool for a while. The fact that you're going to be sharing an office is going to open up plenty of opportunities to have discreet discussions with her and see if anything more is possible. But I caution against you pushing it, because if she isn't ready or interested, you're going to be making both your lives uncomfortable.
Take your time and try to remember that no one has ever died from unfulfilled desire.
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A
male
reader, harshbutfair  +, writes (30 July 2005):
 First things first fella.. Make sure that her boyfriend is not capable of physically hurting you if you steal her from him (as would be his right). If that all checks out okay, I say that you should continue to try to seduce her, but not to the exclusion of other girls in your life.
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