I was looking at SA and stumbled across a profile of a woman who was an intern in our group last summer.  I know her.  We got along great when she was there, in a totally work-related way.  She is drop dead gorgeous and very sweet to boot. The question is what to do. My little head is raring to go. My big head is telling me it would be absolutely nuts to contact her, as she knows who I am and I don't want to risk anything associated with my  job -- to be clear, she no longer works with at my place but it seems like a big risk anyway.  

I would welcome comments both about whether it is nuts to contact her and advice about how to do so, if that is the outcome.  

You brain wants to form an attachment because you find her physically attractive, and you've already completed the hardest part of being with a woman:  The introduction.  That, and finding that she's not repulsed by you and you're not repulsed by her.

 
But remember, there are a LOT of fish in the sea.  You can have your cake (find the connection/intimacy that you want) and eat it too (remain secure and anonymous, if that's your desire).

 
Move on.

...but how significant a risk is it?  

 
She no longer works at your organization. Is there a chance she will work there again in the future?  
Do you have a wife or SO that does not know about your sugar lifestyle?  
Did she become personal friends with anyone at work? With any of your personal friends? With any of their spouses?  
Do you typically take sugar dates to locations where you are (or she may be) known?  
Do you think she has the emotional intelligence to keep a sugar arrangement separate from any mutual friends, coworkers, acquaintances?
What would happen if your social and/or professional group finds out you are dating significantly younger (but over 18) women? What would happen if that woman was the intern?
Has she seen your profile and contacted you?  

 
Have you made "soft contact" by liking her profile without sending a message?   That may allow her to decide if she wants to connect.  

 
If all that seems like a math question you can't solve without more info, then either get more info or move on. Some questions may be better off left unanswered.  

 
Life is good

 
The Cat

details of their personal lives secret from each other as in the P4P escort world?

 
I was under the impression  that this was not the case as the rational for SB/SD was to be able to have more of a relationship rather than a strict customer/provider situation.

 
If this is the case, and there are no longer work/personal issues floating around, then I say why not?   Especially as you already know that she is your type.

 
I'm not suggesting that being careful isn't important, but every worthwhile thing comes with some risk.   You just have to decided where you draw the line.   We can't do that for you.

Why does it bother you that she knows who you are?  I tell my SBs who I am, I don't see any problem.  As for how to contact her I'd DM her on the site, and say Hi, I was delighted to find your profile here.  It's great to know you are interested in this kind of socializing!  It can be amazing when we're both on the same page.  Let's have lunch one day soon and find out!

If she's sugaring she's looking for money.  Think of it that way.  If she's willing to fuck you for money, she may be very willing to fuck you over for it.

If you are really interested in her, perhaps contact her outside seeking?  Offer a coffee meet for mentoring, tell her how much you liked having her in the office and wanted to see how she was doing.  Pretend to be naive to sugar dating, be willing to give it a go since you like her.  

The sugar world is complex and multi faceted. I am of the belief that any connection between your sugar world and work world is extremely dangerous territory. It is unnecessary. Yes, she is attractive. But sugar relationships are designed to have boundaries and endings. Managing both is one of the keys to success. Don’t merge you two worlds in an any way…even if it seems small

Ok so now you have seen a variety of points of view. Only you know which reply resonates best with you.  

 
You might have guessed that this community would not have a single, simple answer because sugaring is complicated. And each of us, as well as each POT SB, has complicated motivations and situations.  

 
What I think you can see from our "help" is that you will need to spend some time really thinking about what your priorities are and how comfortable you are dealing with uncertainty pursuing them.

 
Please let us know what you decide and how it works out. We all will appreciate the opportunity to learn from your experiences.  Besides, I'm pretty sure all of us have some steamy fantasies about hooking up with the Office Intern. LOL  

 
Life is good

 
The Cat

I greatly appreciate and learned a lot from the comments. Thank you all.  I decided not to pursue this.  

I may be paranoid,  but I felt that the connection to work could be problematic.  For example, suppose everything goes great and we have a couple of great dates, and then she says she wants more money or she will say something to HR at work, including that I came on to her while she was there. Obviously, I did not.  But if you even have to have that conversation with the higher ups, you are losing, big time.  I did not want to put myself in that position.  

So, another gorgeous woman I won't have a relationship with.  Not the first, won't be the last.

Thanks again and happy adventures to all of you!

Everything worth having in life has some kind of risk/reward component.  Here, you've decided the "reward" was not worth the risk.  It's unfortunate that you had to analyze the absolute worst case scenarios, but I think that's what these situations require.  There are just too many other viable options in the sugar world.  They are not easy to find, but they are out there.  Best of luck in your search

Smart choice.  Always protect yourself.

...but like you, I'd probably do it.  You only live once.

While I do see the jist of your concerns, screenshots of messages and texts would wipe out anything she could ever do other than embarass herself in the corporate world. If she's no longer at the company I doubt they would take her seriously anyways. I'd go for it...Hell I've banged some of my ex (step)grandaughters festival friends, they have no clue who I am.