A
male
age
,
*iama
writes:Hi this only happens at work lm a guy and really like 2 women 1 is married and find it hard to ask her out for a coffee and chat l feel she's still interested but she wants me to approach her and ask her out l don't think it will happen also cause she's my boss l am nervous towards her and she sometimes feels that way to me, how can l get the courage to ask her out. The other workmate l hit it off straight away with her l have more things in common with her we both get on really well. Last night when l was leaving l talked to the woman who's my boss and she asked if l wanted to talk to her about work or something else is she still hoping that l will ask her out one day. Kind Regards Paul. I really need help.
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female
reader, mystiquek  + ♥, writes (6 October 2017):
 OP, I could understand better your confusion if you were in your early 20's but you are a middle aged man and must know that what you are contemplating is NOT smart. Even if your boss is interested in you, don't go down that road. Office romances rarely work out, cause alot of gossip and normally end with one person being asked to leave or fired. In YOUR case, the boss would probably find a way to fire you. Just don't. The single lady? It would definitely be a better one to ask out but again...its not smart to date someone you work with. I'd steer clear of BOTH women and treat them as co-workers, not possible love interests.
A
male
reader, BrownWolf  +, writes (6 October 2017):
Oh I really hope you get married, or get a girlfriend,that you love deeply. So that some guy can come along takes her away from.
In fact I hope you do not ever get a girlfriend, because you are VERY SELFISH. All you are thinking is about your needs and wants.
Tons of single women out their for you to get...But no...you want to ruin a marriage for your own selfish reason.
Do to others as you would have them do to you.
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A
male
reader, N91  +, writes (6 October 2017):
 Seriously?
You're over 50 years of age for crying out loud. She is MARRIED. Not only is she married, she is your BOSS. You are asking for a world of trouble by even entertaining the thought.
Why on earth would you think trying to date your married boss is a better option than approaching a single woman?
Keep romance and work seperate, you're really playing with fire here. You need to give your head a wobble.
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A
female
reader, Andie's Thoughts +, writes (6 October 2017):
 OP, the fact you want to ask out a married woman says a lot about you - none of it good. Let it go; she's not available.
If you "can't" restrain yourself, ask the SINGLE woman out for coffee (if she's around your age!), but it's advisable not to flirt or try to date either of them.
Out of curiosity, OP, as you seem to have bad judgement on what's appropriate, roughly how old are these two women you're after?
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A
female
reader, Aunty BimBim +, writes (6 October 2017):
 How do you know your boss is interested? Is she leaning over so that you can look down the front of her dress all the way to her navel and giving a little wriggle? Or maybe licks her lips in a salacious way whenever you glance her way? What signs is this woman giving that makes you think she is interested in a little jiggajiggy on the side with her subordinate?
Are you sure you are not misreading the signs, maybe what you take for nervousness is her trying to work out your body language, you do say you get too nervous to ask her out, maybe her asking if you wanted to talk about work or other issues is as a result of her picking up on your weird behaviour.
Unless you are 110% sure you are okay with the risk of making yourself look a prize prat at work I would strongly advocate that you do not approach your boss with a view to a date.
As for the second woman, whose unmarried state seems to make her less desirable because you haven’t mentioned her at all, as already suggested by others on this site, its best to keep your private and working lives separate … because mixing the two sometimes leads to a huge HR mess.
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A
female
reader, WhoInTheTardis  +, writes (6 October 2017):
 I believe you should think this through, thus I am sure you wouldn't be happy to destroy someone's marriage. Are you sure she is interested in you? Maybe she just sees you like a brother, women tend to do that very often.
In my opinion (you don't have to listen to it), workplace romances are not good. Who knows, what if you made a wrong move and she fires you just because of her personal feelings? Be careful!
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A
male
reader, Denizen +, writes (6 October 2017):
 If you have ever - ever looked at this site before you should have realised that the overwhelming opinion of the aunts is to keep work and romance separate. It rarely ends well.Coupled with that you are contemplating, not only chatting up your boss, but your MARRIED boss.Furthermore on your trail to meltdown you are contemplating complicating everything by mixing it with another female at work. Are you a masochist? Mate, keep it zipped and find someone outside of the workplace for your and everyone else's sanity and peace.If I can give it to you straight - at your age you ought to know better by now. This doesn't bode well for any of you. The female boss, female colleague and you, triangle has danger on it writ large.
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A
female
reader, Honeypie + ♥, writes (6 October 2017):
 The woman who is your boss is married. There is no need for you to invite her out for coffee... If you need to talk work, do so at your WORKPLACE.
She likes the attention doesn't mean she is REALLY looking for more.
And workplace romances are rarely a smart thing. If it doesn't work out, you still have to work with her. Either of them. Or you create an uncomfortable atmosphere if either lady really isn't interested. Your workplace is not a dating club. Y'all are there to work.
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