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Topic: dating my boss?
CharlotteRae's photo
Fri 09/18/15 06:16 PM
I've worked at my job for 2 1/2 years and have always wanted to ask my boss on a date... He owns the place I work at... So he is rarely there... He has done nice things for me such as giving me money and checking up on me when I'm feeling ill... But I can't figure out if he's interested or just being nice bc he knows I'm a single mom... If I asked him out for drink would that be so wrong?

no photo
Fri 09/18/15 06:19 PM
U'll never know until u try right? He can't fire u coz u ask him for a date right? Have the courage, go for it!

Do drop by again and let us know how it went. I'd love to hear it

mightymoe's photo
Fri 09/18/15 06:23 PM

I've worked at my job for 2 1/2 years and have always wanted to ask my boss on a date... He owns the place I work at... So he is rarely there... He has done nice things for me such as giving me money and checking up on me when I'm feeling ill... But I can't figure out if he's interested or just being nice bc he knows I'm a single mom... If I asked him out for drink would that be so wrong?


you didn't mention if he's married or not...

TMommy's photo
Fri 09/18/15 06:26 PM
well let me just throw out this little scenario

say you do go out
get all hot and heavy with each other
and it lasts a few months and then..
you have a falling out
and work place becomes difficult to be around
each other..

who do you suppose is going to end up leaving?
the boss or the employee?

TrystaBella85's photo
Fri 09/18/15 06:27 PM
Edited by TrystaBella85 on Fri 09/18/15 06:30 PM
Mixing professional and private life rarely works out. If you guys go out and get into a relationship and then break up, can you still work for him? Would it be weird for you? Would you want special treatment at work and then get offended when you don't get it? Or if you do get it and your co-workers find out, won't that be awkward? Just my thoughts.....I dated 2 guys I worked with (not at the same time) and when the relationships ended it was very very hard to work with them anymore. I can't imagine if they had been my boss, I guess i might have quit. Maybe.

no photo
Fri 09/18/15 06:28 PM
This is a real bad taste of mine moe...

i am attracted to married men

TrystaBella85's photo
Fri 09/18/15 06:28 PM

well let me just throw out this little scenario

say you do go out
get all hot and heavy with each other
and it lasts a few months and then..
you have a falling out
and work place becomes difficult to be around
each other..

who do you suppose is going to end up leaving?
the boss or the employee?



My thoughts exactly....

SitkaRains's photo
Fri 09/18/15 06:28 PM

I've worked at my job for 2 1/2 years and have always wanted to ask my boss on a date... He owns the place I work at... So he is rarely there... He has done nice things for me such as giving me money and checking up on me when I'm feeling ill... But I can't figure out if he's interested or just being nice bc he knows I'm a single mom... If I asked him out for drink would that be so wrong?


What are the office policy about interoffice romances most places have a Strict no dating policy.

I personally wouldn't do this unless I would be interested in finding another job.

The best is he goes out for a drink with you, you guys start something and for whatever reason done the road it doesn't work out. Then what?

If it does work out will you expect preferential treatment then there is chaos with other staff.


IF he is worth doing this then ask him out at the same time you give notice and give the reasons why, he is more interesting and a better opportunity than the job.

Just my humble opinion.

TrystaBella85's photo
Fri 09/18/15 06:29 PM

This is a real bad taste of mine moe...

i am attracted to married men


Good luck with that. They rarely leave their wives, and if they do, rest assured they'll leave you for an upgrade.....

no photo
Fri 09/18/15 06:29 PM
I got fired once for having a relationship with a fellow colleague

no photo
Fri 09/18/15 06:32 PM


This is a real bad taste of mine moe...

i am attracted to married men


Good luck with that. They rarely leave their wives, and if they do, rest assured they'll leave you for an upgrade.....


In Islam, wrecking marriages is a sin. Men can marry up to 4 women. I have a best friend who has 4 wives and 21 children. They all live in harmony
I am close to their family, often go out with them

TrystaBella85's photo
Fri 09/18/15 06:39 PM
I have yet to meet a d1ck that's more valuable that my job and I hope I never do. smh

TrystaBella85's photo
Fri 09/18/15 06:39 PM



This is a real bad taste of mine moe...

i am attracted to married men


Good luck with that. They rarely leave their wives, and if they do, rest assured they'll leave you for an upgrade.....


In Islam, wrecking marriages is a sin. Men can marry up to 4 women. I have a best friend who has 4 wives and 21 children. They all live in harmony
I am close to their family, often go out with them


Oh okay, I meant in America, I forgot not everyone is from here.flowerforyou

CharlotteRae's photo
Fri 09/18/15 06:51 PM
Not married and no kids... He is actually trying to sell the business... After his mom passed away he got stuck with it... I'm not leaving my job if it doesn't work out and there's only 5 of us that work there and they all know I have a crush on him...

motowndowntown's photo
Fri 09/18/15 06:54 PM
Just a little friendly advice from an old man; DON'T POOP WHERE YA EAT!

TrystaBella85's photo
Fri 09/18/15 07:04 PM
Great advice.laugh drinker

no photo
Fri 09/18/15 07:28 PM

Just a little friendly advice from an old man; DON'T POOP WHERE YA EAT!


I quite agree

no photo
Fri 09/18/15 09:00 PM
there is NO NO NO way that is a good idea. trust me i have heard to many people tell me about the out come of such things.

Dodo_David's photo
Fri 09/18/15 09:07 PM

I've worked at my job for 2 1/2 years and have always wanted to ask my boss on a date... He owns the place I work at... So he is rarely there... He has done nice things for me such as giving me money and checking up on me when I'm feeling ill... But I can't figure out if he's interested or just being nice bc he knows I'm a single mom... If I asked him out for drink would that be so wrong?




No! Do NOT try to date him. Doing so would be asking for trouble.

Goofball73's photo
Fri 09/18/15 09:19 PM

I've worked at my job for 2 1/2 years and have always wanted to ask my boss on a date... He owns the place I work at... So he is rarely there... He has done nice things for me such as giving me money and checking up on me when I'm feeling ill... But I can't figure out if he's interested or just being nice bc he knows I'm a single mom... If I asked him out for drink would that be so wrong?


Big mistake. Date the janitor.....I hear he has a Mercedes. laugh

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