Should I ask out my bosses granddaughter?

[Macaframalama]

So, my bosses granddaughter has just went through a divorce and I've been contemplating asking her out, but not sure wether I should be mixing business with pleasure. Her grandfather owns a multi-million dollar company that he created from the ground up, which is ran by the whole family. She actually cuts my checks, her mother is the lead accountant on the way out and her uncle runs the day to day, so there's the potential to royally fvck some chit up. We gel pretty well as far as convo goes and have had some lengthy talks, but I've been leery of attempting turning it sexy at all. She would also be the most attractive girl I've dated, but the older I get, the better looking and younger the girls I'm picking up are getting, so I'm confident, but if I was to put money on it, I would give myself a 40/60 chance realistically of her saying yes. I don't like living with regret, but I could also possibly end up regretting losing a decent paying job, that I've worked for 5+ years.

 

[RedScorpion]

Go for it. But don't be surprised that if things go downhill with this girl, then she's going to be expressing herself to those closest to her. Especially since it's a very tight knit company-family group. Depending on what happened and how she handles a split between you two - could range from minor repercussions to major.

You already know the risks at hand here.

 

[AJ84]

I don't think it's a good idea.

A just divorced woman, related to your boss and involved in the family business, it's all too close to your job security. If it doesn't work out and she feels hurt by you what could the consequences be?

Not worth it, in my opinion. Family run businesses are very loyal to each other and will do things that other employers can't easily do, like find a way to sack the guy who pumped and dumped the granddaughter of the owner of the company.

 

[Macaframalama]

Yea, I didn't even think of the consequences of if it did end up going somewhere and ending badly later down the line.

 

[El Payaso]

Unless you don't care about your job then go for it.

In my experience, dating coworkers or anything of the like always leads to disaster.

 

[TheGambino]

I would say no

 

[That_dude]

That’s a recipe for disaster. I wouldn’t.. Thats just me though

 

[A 3% Percent Man]

You don't $hit where you sleep.

 

[TheGambino]

Women are everywhere, dont sheit where You sleep.