Dear Sasha, A couple of months ago I was introduced to a wonderful man by mutual friends.  We have been dating since then and things are going really well, he recently invited me to fly to his hometown to spend the weekend with his family. Things are getting serious… we are both in our early 30s and looking for a long term relationship.  We are deliriously happy.

The only catch is that I work with his ex. They dated for about a year and a half and lived together briefly.  We are both professionals working for a large company.  We don’t work directly together, and we aren’t close friends, but we do work in the same business unit and sit on the same floor (I see her a few times a week and we are friendly).  He broke up with her about a year ago and they are no longer in touch.

Should I sit her down and tell her I am dating him before she hears through the grapevine? She is truly a lovely person but I really do not know how she will react to this. Help! T  


No no no no no, you should not be the one to break this news to her. And what? Were you thinking of telling her this at work?! Oh lord, no no no no no. Seriously T, you could craft up the kindest, most supportive, non-threatening delivery in the world and she’d still want punch you in the gunt.  
Look, I give you props for thinking about how your relationship will affect her, and I get how slimy it must feel to see her all the time; having to smile her way knowing full well that you’re f-cking her ex, but you can’t be the one to break the news to her. This one is up to your homie. 

How he wants to tell her is up to him, but he needs to tell her on the double; ideally before you meet the family because as soon as that happens, word will spread, and as soon as that happens the potential for you having a bitter ex on your hands will be a high-ass probability.

So bow out of this one and let your man handle it. Keep me posted and thanks for writing in! xx