When do I put all my eggs in one basket?

[+TenPercent]

Quick background: 10 months ago I saw a woman leaving my workplace and my jaw dropped. Instant attraction. Turns out she had just started working there . . .
Over the past 10 months I have had other attractions, sure, but she's at the top of my list. It's clear that the attraction is mutual, and she has to know that I'm very attracted to her but I have chosen not to take action mostly because I have been too busy for a relationship. She is very flirty and this means that I have had to watch her flirting with other guys (not ideal for a guy with cuck fantasies). I've held on. If I am going to date this woman, I want to have time for her.

That time is now. I was in Brussels last weekend and bought her a box of chocolates (hand selected, no hearts) and this week I did the very terrifying thing of approaching her at her desk and offering her the chocolates. It went well!!

And now, the cat is out of the bag. She knows that I like her and I have made a move. I imagine the next step would be to ask her out on a date (probably something casual like coffee).

I'd like to be cool and casual. Truth is I fear messing it up (I was visibly nervous when I gave her the chocolates and could barely talk). I can flirt very easily with women when I am not that interested, but this one really is something special . . .

So my conundrum is: do I act as if she is definitely going to be my girlfriend soon (manifestation, if you will) or do I try to carry on, business as usual, as if my world won't come crashing down on me if this doesn't work out?

In particular, there is a femdom party that I was going to attend on Saturday. This doesn't seem in line with the idea that I will be dating the woman of my dreams soon.

(Underneath that perhaps is the fear that I am not okay as I am at the moment. That I need to become someone else for this woman. A fear that she will freak out and run the other way if she finds out that I am into bdsm)

Any advice would be helpful. Thanks!

 

[Coolyorky]

Personally I’d leave the bdsm and get with the girl bro

 

[+TenPercent]

Personally I’d leave the bdsm and get with the girl bro

I haven't even been on a date with this woman yet, I'm inclined to agree.
I already have this sense that I would be willing to give up bdsm (and much more) for her.

But then I worry that I would be "losing myself", changing who I am for what I think someone else wants me to be . . .

And, maybe I will find out that she's kinky, too?

 

[The Wrestler]

So my conundrum is: do I act as if she is definitely going to be my girlfriend soon (manifestation, if you will) or do I try to carry on, business as usual, as if my world won't come crashing down on me if this doesn't work out?

How about treat this as practice? You cannot fail at practice...

 

[+TenPercent]

How about treat this as practice? You cannot fail at practice...

I'm not entirely sure what you mean. Do I treat the whole thing (all of life) as practice? Because, it's true and its a good way to approach life. In that case, I can pick either course of action and simply see what happens. It's practice. I will learn something either way.

 

[Ra's Al Ghul]

Be yourself, and whether or not she becomes your girlfriend is thinking too far ahead. This chic may have her pick of Turbo Chads if she's as hot as you describe her. So just relax and let things flow naturally. Trying to be someone who you're really not will eventually catch up to you. Have fun,not every gal we meet is meant to be with us long term.

 

[Catch22]

I'm not entirely sure what you mean. Do I treat the whole thing (all of life) as practice? Because, it's true and its a good way to approach life. In that case, I can pick either course of action and simply see what happens. It's practice. I will learn something either way.

You dog lol what a great play on devils advocate lmfao

 

[Deleted Account]

How about treat this as practice? You cannot fail at practice...

He could fail and the failure could have devastating consequences. He could end up getting fired. It's foolishness to get involved with someone you work with!

I was in Brussels last weekend and bought her a box of chocolates (hand selected, no hearts) and this week I did the very terrifying thing of approaching her at her desk and offering her the chocolates.

Big mistake! You haven't thought this through, have you?

 

[Catch22]

He could fail and the failure could have devastating consequences. He could end up getting fired. It's foolishness to get involved with someone you work with!



Big mistake! You haven't thought this through, have you?

This is why other people’s opinions are dangerous. This is spot on bro. He’s got to be true to himself.

 

[ReclaimedLife]

Work place relations are always VERY delicate. You might end up being fired and you might end up with the woman you fall in love with and marry.
There are literally no stakes higher then the ones of having a romance at the work where you really enjoy doing your Job.

I would only approach her if you are 100% sure that getting fired from this job wouldn't change your life at all and you will find a similar or better Job in a short period of time.

 

[+TenPercent]

He could fail and the failure could have devastating consequences. He could end up getting fired. It's foolishness to get involved with someone you work with!



Big mistake! You haven't thought this through, have you?

and @ReclaimedLife @Catch22 - thank you for the responses. I've been thinking this through for months.
To make matters worse, she works in HR!

I truly wish that I could have met this woman anywhere but at work. I didn't want to write a painfully long initial post, but my top two reasons for not asking her out over the past 10 months were:

1. I was too busy for a relationship. And,
2. I am very wary of dating people at work.

At least we don't work in the same department. I have been very deliberate about this. There are other cute girls at work, but I figure I only have one chance at this. I don't want a reputation as the guy who's always trying to hook up with women at work.

 

[Deleted Account]

I truly wish that I could have met this woman anywhere but at work.

Yes. Can you find a job elsewhere? It might seem a bit extreme but if I worked with a woman I liked and she was worth pursuing I would get a job elsewhere and then ask her out. I suppose it isn't as bad as I first thought since she works in a different apartment but still not ideal in my opinion.

 

[+TenPercent]

I think I found the answer. In short, it's not yet.

I have been depressed all week and am finally getting clarity on why.

For 10 months I've had this crush, convinced that she likes me, but frustrated that the timing wasn't right for me. At the same time, I wondered how much I was just a toy for her. A pawn. One of half a dozen chads at work vying for her - while she was getting her ego stroked and soaking up all that male attention.
She really seemed so f'ing attracted to me that I thought I was special.

Well, maybe I'm not. At least, not to her. I took a really big gamble with my actions last week. I opened up my heart and let the cat out of the bag. What has happened since? Not much. Our paths just don't normally cross at work, and she's done nothing to change this. She's still flirting with other guys (though she seems really happy to see me when we do see each other - on average maybe 4 or 5 times a week).

I almost can't believe that I am manning up enough to say this but . . . I don't want to be one of half a dozen guys that she flirts with at work. Fuck that. I want to date her. I want to take her out on a date and see if we have any potential. I want to be with her outside of work. Flirting at work is just a waste of my time.

And tonight I literally felt like slapping myself on the forehead. Did I really write what I wrote in my original post?? In fairness, I thought that perhaps a relationship with this woman might be imminent. But I have to accept that it is not. I would be a fool to give up parts of myself for this girl before we even started dating. This whole fucking week I've been trying to think of who I need to be for this girl to choose me. Fuck that. I just need to focus on becoming (or just being) who I want to be. Half the reason why I was so attracted to this girl is that she seemed to be really into me. She either is or she isn't. Trying to change myself into what I imagine she wants me to be is a losing game. I literally can't win that game!!

Thank you everyone for your feedback. It really, really helped!