What should my strategy be? Falling for a coworker.

[NumberCruncher]

I'm admittedly nervous about jinxing myself by posting this on the Internet but I really could use advice.

So, I've become interested in this cute co-worker. She's an amazing person and the more I interact with her, the more interested I am in her.
Usually, with women, it's the reverse situation.
If it wasn't for the professional relationship, I'd have already asked her out.

We definitely connect very well. I get good vibes from her and we have very fun/comfortable interactions. We also have spent a lot of time together (at work and the occasional happy hour) and already know a lot about one another. She has responded well to my playful flirting/teasing.
For obvious reasons, I've avoided any sort of physical flirting, but I'm good at the verbal flirting.
I've also been giving her a lot of advice/motivation on the job lately. I have about 1.5 more years of experience at the job, so I've been eager to help her out with things.
I'm also trying to play it cool now and not become too attached with her, but we connect extremely well.

I have been casually dating other people but no one who has quite piqued my interest like she has. Definitely not. It helps that I have a lot in common with this coworker. Would it be a good idea to pursue something more with somebody else to see if I can make my coworker jealous? We're both single at this time.

Ideally, I'd love to just jump right in but the whole office relationship thing could create a ton of awkwardness and could ruin whatever great connection we have right now.

If you need any more details to provide advice, please send me a PM and I'll do my best to explain things further. There are some things I have deliberately omitted which I would include via PM.

[Wakeup]

Instead of playing a stupid game of trying to make her jealous, why don't you just ask her out on a proper date (use the word date in there somewhere when you invite her out to do something fun [other then drinking booze]) and advance your high school flirting to something more?

If she turns you down then at least then you can start to do the mental work you need to do to get over your crush and you can actually date someone else because you find her attractive and interesting rather then use her to make another girl jealous.

[NumberCruncher]

Instead of playing a stupid game of trying to make her jealous, why don't you just ask her out on a proper date (use the word date in there somewhere when you invite her out to do something fun [other then drinking booze]) and advance your high school flirting to something more?

If she turns you down then at least then you can start to do the mental work you need to do to get over your crush and you can actually date someone else because you find her attractive and interesting rather then use her to make another girl jealous.

Yea you're right. It would be a stupid game to play. It wouldn't be fair to the other girl either.
I guess this leads to some questions I have as to overall strategy.

Chances are decent that I may actually be leaving my current job for a different one late spring/early summer. I have to make an overall assessment regarding how I feel about my current work environment. A lot of good and bad mixed in. I already told this girl I'm likely going to be leaving soon. A part of me was thinking of waiting to ask her out until I know if I'm leaving or not.

I guess I'm terrified of the awkwardness which will come about if she turns me down. I feel like we really have a connection going and it would suck to see it fizzle out and dissipate into nothingness especially if we're both working together.

If I choose to ask her out while we're both coworkers, how should I go about it? What should I do? What should I not do?

[mofugga]

What kind of work do you guys do??
Many places frown upon dating within. What's both of your ages?

[NumberCruncher]

What kind of work do you guys do??
Many places frown upon dating within. What's both of your ages?

We're both auditors at a public accounting firm. We work in the same department too. There's nothing in the employee handbook which explicitly disallows dating within the office. But it could be different implicitly, not sure.

I'm 26 and she's 24. So we're pretty close in age.

[mofugga]

Remember stuff can get messy at work if something goes wrong or someone gets jealous, and that can jeopardize our jobs. Remember the motto don't shit where you eat. But its ur call. Maybe it will be warmth assuming u guys are up north.

[NumberCruncher]

Remember stuff can get messy at work if something goes wrong or someone gets jealous, and that can jeopardize our jobs. Remember the motto don't shit where you eat. But its ur call. Maybe it will be warmth assuming u guys are up north.

Yea, it's a risk I really need to decide whether I want to take it or not.
That's kind of why a part of me wants to wait until late spring/early summer to decide whether I want to ask her out or not.
I already told her that I was seriously considering switching jobs at that point of time.
However, there are certain reasons why I might want to stick working where I'm at.

But at the same time, I don't want to blow my chance with her by asking her out too late. I'm going to be really facepalming if I learn she got a boyfriend by the time I switch jobs.

And yep, we're up north... sooo cold out....

[smackie9]

Why not ask her and some co-workers to go out for drinks after work. See what she is like outside the office first. This would be your opportunity to get to know more about her personal life, ie: BF.

[NumberCruncher]

Why not ask her and some co-workers to go out for drinks after work. See what she is like outside the office first. This would be your opportunity to get to know more about her personal life, ie: BF.

Not a bad idea, once the busy season is over. It would be a good opportunity to learn more about her and her personal life.
As of now, I know there is no boyfriend but anything can happen in the near future.

[GemaaaSpirit]

time is always limited, have that in mind and don't wait too much either
anecdotes,anecdotes..

[snoopy1983]

I'd ask her out if I was you.

You are both young anyway, there's always way to change jobs if it really gets to that point, but that doesn't mean it should.

And well, afraid of spoiling the connection between you? You have to be honest that it is not a "mutual friendship" if you have feelings for her in the first place. So all you are doing is lying to yourself and her that you are friends. The longer you wait on telling her, the more difficult it will become to do so. And you are both single anyway, so I don't see a problem?

[NumberCruncher]

time is always limited, have that in mind and don't wait too much either
anecdotes,anecdotes..

Thanks
I will keep that in mind.

- - - Updated - - -

I'd ask her out if I was you.

You are both young anyway, there's always way to change jobs if it really gets to that point, but that doesn't mean it should.

And well, afraid of spoiling the connection between you? You have to be honest that it is not a "mutual friendship" if you have feelings for her in the first place. So all you are doing is lying to yourself and her that you are friends. The longer you wait on telling her, the more difficult it will become to do so. And you are both single anyway, so I don't see a problem?

That's true about the whole lying to myself thing.
I just really enjoy her company and am afraid of losing that if I ask her out and she turns me down. She is one of the main reasons why I can even feel excited about going to work.

However, things would be so much better if I asked her out and she said yes

How should I go about asking her out? I think it would be best to get us in a situation where it is just the two of us and I can ask her there.

I also may be switching jobs soonish anyway. I told her this already. If I decide to switch jobs, it would be in late spring/early summer. Should I take the chance that she's already expecting me to ask her out during my two week notice? Or could that be one of those "crap, I did it too late" kind of things?

[snoopy1983]

Well, I like the simple approach.. so why don't you just ask her to go and have a coffee (or another drink) after work? This might not be a real date, but it's the first step to asking her out on a real date and this might tell you a little more about how she feels about you.

I'd have a coffee with both a friend and a lover, so if you feel insecure or it turns out that during your coffee she seems not interested, you can still turn it into something positive. The way she looks at you tells you a lot.. does she look you in the eyes, what happens if you look her in the eyes? This will also give you an opportunity to talk a little, it might make her feel safer to go to such a place the first time than a party or a restaurant. If you are serious about her, then you need to take it slow anyway, she will let you know if she wants to take things faster I'd do it now if I was you, there is no real reason in waiting for your 2 weeks notice. You can start by giving out simple hints that you like her (a little compliment), if she doesn't get it immediately, you'll have to be more direct. You can always ask her to go for a second coffee another day. If it turns out she is not interested, then just tell her that you wouldn't like this to jeopardize the relationship you have as co-workers and you will keep things professional and friendly.

Source: My co-worker and friend told me (after more than 10 years, I'm 31) that he is in love with me but didn't tell me as he didn't want to lose our friendship and I am in love with him too I just wish he'd have told me sooner, that would have avoided a whole lot of problems. And I've always been able to work with him perfectly in the same department of our office, so that doesn't mean anything.

[NumberCruncher]

Well, I like the simple approach.. so why don't you just ask her to go and have a coffee (or another drink) after work? This might not be a real date, but it's the first step to asking her out on a real date and this might tell you a little more about how she feels about you.

I'd have a coffee with both a friend and a lover, so if you feel insecure or it turns out that during your coffee she seems not interested, you can still turn it into something positive. The way she looks at you tells you a lot.. does she look you in the eyes, what happens if you look her in the eyes? This will also give you an opportunity to talk a little, it might make her feel safer to go to such a place the first time than a party or a restaurant. If you are serious about her, then you need to take it slow anyway, she will let you know if she wants to take things faster I'd do it now if I was you, there is no real reason in waiting for your 2 weeks notice. You can start by giving out simple hints that you like her (a little compliment), if she doesn't get it immediately, you'll have to be more direct. You can always ask her to go for a second coffee another day. If it turns out she is not interested, then just tell her that you wouldn't like this to jeopardize the relationship you have as co-workers and you will keep things professional and friendly.

Source: My co-worker and friend told me (after more than 10 years, I'm 31) that he is in love with me but didn't tell me as he didn't want to lose our friendship and I am in love with him too I just wish he'd have told me sooner, that would have avoided a whole lot of problems. And I've always been able to work with him perfectly in the same department of our office, so that doesn't mean anything.

Wow, thank you! I might just go ahead and do that. I will just have to gauge what the right time is going to be. March is an incredibly busy month for both of us work wise.