Do I make it official

I am a 35 year old professional woman and I work in advertising, I got divorced 5 years ago after 12 years of marriage and 3 children when I caught my husband cheating, I dated in the beginning mostly out of spite which I realized was not the right way to deal with the situation, We share custody and I only dated so my kids would tell him I was dating and it didn't take long to realize it was upsetting my children so I stopped.
3 years ago I got promoted and had to hire a personal assistant as it is basically a requirement of my position that I never answer my own phone or schedule my own appointments which in the beginning was very annoying but I now don't even give it second thought, I went through a couple assistants before finding Shelby, Shelby walked in and had an air of confidence but not cocky, Then 24, She was dressed and presented herself impeccably, She had wonderful credentials and I hired her on the spot.
Shelby now schedules every aspect of my life, I don't know what I would do without her but my bosses say I have to promote her, they want her to take on a roll more similar to mine which she is absolutely ready and I have been training her for.
BUT...2 years ago we started a "Relationship", I was lonely, we both had drank too much and I woke up naked in bed with my assistant, to be honest not much happened, Some touching and kissing, I immediately sat down with her and explained that it was not something that could continue and it had to be forgotten about and never brought up again, She was a bit upset and stated her position but at the time I couldn't fathom what had happened and there were just too many reasons why it was not a good idea, I had not been with a girl before which didn't make things any better just coming to terms with the fact that I had stepped so far out of my comfort zone.
2 months later on a business trip Shelby booked us a suite as always and I woke up in the middle of the night to her laying behind me kissing my neck and touching me, No excuses but by the time I woke up I was beyond the point of stopping her and I feel that night was when I broke through a lot of boundaries, We had a talk the next morning and I decided that I wanted to pursue things more.
We started just doing stuff when out of town which was about once to twice a month then she started staying over when the kids were with my ex, I haven't figured out how to take the next step and introduce her to my children as "My girlfriend" let alone my friends, The whole work situation is a tough one, Once she is on a level with me as a coworker and not my assistant there shouldn't be any issues, we just cant tell anyone it started before that point.
Since we wont be traveling together anymore the amount of time we get together would be less and it would just be easier to put it out there that we are together and not have to hide it anymore, We have discussed it and she wants to I just am not sure I know how to do it yet, With children it is a delicate issue and I need to be careful and prepared as to how I approach and explain it as well as answer any questions or concerns they have.


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  • How old are your children?

  • Please change your profession

  • Idiot

  • Here are some questions. It's nice that you have found one another, because love is love. It sounds like you both get a long very well. Maybe the questions you need to ask each other is just how serious you want to take this. Is she Ms. Right or just Ms. Right now? Are you going to tire of her and want a man again? And just as you said how do you introduce her to your children, how does Shelby fit in with your friends and family? Is your workplace open to having coworkers date? What is Shelby's hope for a future? Is she strictly a lesbian or bi? And you? It doesn't have to be concrete answer by any means, but you have had your children.. if you stay together are more kids an option..This sounds like something you and Shelby need to discuss first before even introducing her to your kids.

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