Dating your boss..

Old Nov 18th 2009, 12:05 pm
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Default Dating your boss..

The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".

Last edited by Euc-; Nov 18th 2009 at 12:16 pm.
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Old Nov 18th 2009, 12:07 pm
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Default Re: Dating your boss..

That's got to be a bad idea.

I believe the correct phrase is 'don't sh!t on your own doorstep'


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Old Nov 18th 2009, 12:19 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".
Sounds like she either really does like you in "that" way or she thinks you are gay. Best bet is to get her more drunk than you one night.... try your luck and if she doesn't want your attention tell her she came on to you first
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Old Nov 18th 2009, 12:32 pm
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Default Re: Dating your boss..

recipe for disaster...what happens if you get together and then it all ends, do you lose your job too...

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Old Nov 18th 2009, 12:50 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".
tough that...you may be in trouble if you don't do it,and you may be in trouble after you've done it.
Best to tell her you are gay ....
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Old Nov 18th 2009, 1:39 pm
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Default Re: Dating your boss..

Lifes too short! I say go for it!

Although imagine you go on a date- you realise shes clingy, needy possessive and a bit of bunny boiler, you're not so keen but she thinks your her future husband.... hmm not the best of situations to be in- are you prepared to leave your job if it all goes horribly wrong?

good luck and let us know what happens!

There is a saying don't mix business and pleasure but depends how horny you are I guess

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Old Nov 18th 2009, 2:05 pm
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Default Re: Dating your boss..

There are possibly four ways this could go.

1. She really likes you and you attempt to distance yourself from her, she takes it badly. Your life is made a living hell.

2. She really likes you and you go for it, things get messy and it ends badly. Your life is made a living hell.

3. She really likes you and you go for it, she's your soul mate, you get married. Your life is made a living hell.

4. She only sees you as a mate, you make a move and are rejected. Your life is made a living hell.

I say go for it, then when it goes badly you can keep us all entertained with the story and we can all tut tut and say "We told you so"
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Old Nov 18th 2009, 2:44 pm
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Default Re: Dating your boss..

Originally Posted by Alexa View Post
tough that...you may be in trouble if you don't do it,and you may be in trouble after you've done it.
Best to tell her you are gay ....
This would be my advice too!
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Old Nov 18th 2009, 2:49 pm
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Default Re: Dating your boss..

Originally Posted by soukie View Post
This would be my advice too!
Ah to hell with it, go for it, bang her and then claim sexual harrasment if it goes **** up
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Old Nov 18th 2009, 3:03 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?
If this goes tits up, just remember that here its not so easy to just resign from one company Friday and start with another Monday. Use the big head, not the little one.
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Old Nov 18th 2009, 3:06 pm
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Default Re: Dating your boss..

I dated my boss once.

It started with an innocent social drink, which gradually started to happen more often, then it was going to the cinema together, then meeting at weekends........ etc............. etc............

In the end, I felt I had to end it.

In any case, he was fifteen years older than me, and his wife was starting to stick her nose in...........
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Old Nov 18th 2009, 4:24 pm
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Default Re: Dating your boss..

Dean, what you're describing is very very common..

It happened to me as well a couple of years ago. My girlfriend thought i didn't spend enough time with her and my boss' wife was upset that he was out drinking with me all the time.

I was fine about it for ages as it was usually free booze (on expenses), but sooner or later the 'break up' is inevitable...

The tension in the office was thick for about 3 minutes. You could cut through it with a knife..

EUC- ... I'd say go for it. Give her the attention she wants/deserves, but make sure she thinks that she seduced you. That is then your way out...She will probably fire you when it blows up eventually, but hey, think about the nice leaving package you can negotiate (and of course a NOC)..
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Old Nov 18th 2009, 4:29 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".
You are already dating, in every sense except the sexual sense. I think she is making it absolutely clear that she wants you around her - it's the next step....

......... so why not come straight out and ask her? "You and I have been spending a lot of time together, and I really enjoy our relationship. I'd like to make it more serious, but I know you're the boss, so I'm a bit nervous......"

She's not going to fire you for that - if she wants the same thing, she'll have you in bed within the hour. If she doesn't, she'll back off, having realised the impression she has been giving you.

Nothing to lose.
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Old Nov 18th 2009, 5:43 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".
Here's what i'd do. Both go out together....get properly hammered, see what happens.

You already go out a fair bit by the sounds of it so rather than going for the old 'can i take you out' just suggest drinks somewhere...at least that way it doesn't look like a date if nothing happens. If it does happen then well, its probably want you want anyways.

Just beware though....she'll probably want to make you her b*tch at work if all goes well. Caveat emptor (n all that).

P.s. Don't leave it too long to go in for the kill as you may end up trapped in that 'friend zone'.

Last edited by CeeBee; Nov 18th 2009 at 5:45 pm. Reason: Additional pearls of wisdom
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Old Nov 18th 2009, 8:17 pm
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Default Re: Dating your boss..

Originally Posted by Euc- View Post
The million dollar question, what to do (yani)?

Been working with her for a while now, and right from the beginning we kinda hit it off (I think). We go shopping, have dinner/drinks after work, her texting me at random timings to go out and do something together, she invited me to join her at a concert in AD and being flirty with me all the time.

Now the thing is, this all could be explained as her just being friendly and I will probably be in big shit if I misread everything (at least a very big embarresment), so what do I do with it?

Try my luck and go for it, with all the consequences if it fails? Or just forget about it and find someone else? ( )


Not that it matters, but she is not "western", she is Asian but not from the "mail-order category".

What if she's the one mate? You gotta give it a go.

Millions of people met partners at work!
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