I (26m) had a fwb relationship with my former boss (52f) but now I'm dating her daughter. (27f) What do I do now?
Aug. 11, 2019
Long read ahead
When I first met my boss "Mary" I was 22 years old and had recently started working as a software engineer at a relatively small company (that will remain unmanned) to build up experience for my resume. This job oppurtunity was a great starting point for me considering that I was fresh out of college.
As you can imagine, the field of computer science is a very solitary environment. However, Mary and I got along pretty well from the very beginning and would regularly have conversations about our lives outside of work and considering people rarely spoke to each other, we enjoyed the each other's company. For the first couple of months everything was kept professional. Our talks did not over step into inappropriate territory (mostly pertaining to work and the occasional lunch outside of work to discuss future projects). However, as more time went on we talked more about our own lives and a little less about work.
Mary was divorced/single and I had gotten dumped by my gf. At this point, both of us were flirtatious with each other and it was evident that there was attraction on both sides. It was clear that we both intended for something to happen between us because meetings about projects that could easily be held over skype were now held in person. Mary and I would start seeing each other outside of work more frequently. Eventually group meetings became one on one until we finally made the move to fwb.
We we're open with each other in regards to our to our relationships and what we wanted out of sex, but the one topic we didn't talk about was family. All I knew in that regard was that Mary had a daughter and was a single mother.
Fast forward 3 years later and I get a better job offer and the fwb relationship with my boss ended when I moved away. While working for this new company, I meet a girl named "Olivia." Her and I would collaborate on projects frequently even though she works for our sister company. Eventually Olivia and I developed an interest for each other. While we haven't made our relationship official, we have been seeing each other exclusively for 5 months now and really want to move to the next step.
Now the actual problem. Olivia was mentioning visiting her mom and the topic of family obviously came up. Olivia had mentioned that she was raised by a single mother who also worked in the same field as us. That situation happens to a lot of prople, but the problem is that Olivia is the daughter of my former boss (just my luck, I know.) Olivia showed me some pictures and inimmidiately recognized my old boss.
I really like Olivia and want a relationship with her, but if that is to happen, contact with her mom is unavoidable. What do I do at this point? How do I tell her?
Any advise is greatly appreciated.
TL;DR: Had a fwb relationship with my former boss and now I'm dating her daughter. Had no idea
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