“I’m Nervous Sparks Will Fly When He Has a Family Dinner with His Wife”

I started working in healthcare about three to four years ago and was hired by “Chris.” Chris is 18 years older than I am, but I was instantly attracted to him. I wanted to keep our working relationship professional, but after a year, one drunken night, I sent him a text saying, “I think you’re attractive.” We had texted before but only friendly, work-type conversations, so I guess at that point I was comfortable texting him. Moving forward to a year and a half later, Chris has been legally separated from his wife of 25 years for five months (and separated for nine months, total). His wife started dating a few months after they broke up.

The issue I’m having at the moment is: His daughter does not like me for “breaking up the family.” She has asked to have a family dinner this Sunday, and I’m nervous that sparks will happen between Chris and his wife and that he will go back to her and live happily ever after. I have made my expectations clear that I do not feel comfortable about this dinner, but he throws at me that “I’m stressing him out” and “stop please.” Should I be worried? — The Other Woman

If you think dating someone who isn’t committed to you, who feels conflicted about being with you, whose family doesn’t like you, who doesn’t seem to respect you, and who has proven to not be faithful to the woman he’s in a relationship with are all worrisome, then, yes, you should be worried.

You were right all those months ago to keep your relationship with Chris professional only. When you crossed that boundary, you opened your life to all the consequences of pursuing a married boss – consequences it seems you’re just now beginning to realize.

Your boss’s daughter is justified in her feelings for you. You did contribute to the break-up of her family. Because of that, you already have a long road ahead in earning her trust if you want to ever feel welcome in Chris’s family. But add the other hurdles you’re now facing on top of that – your insecurity around Chris’s relationship with his ex, and his general dismissiveness of you (you stress him out, etc.), and the road ahead suddenly becomes even rockier.

My advice would be to start looking for a new job, end your doomed relationship now before even more damage is done, and get yourself into therapy to begin addressing why you sabotaged your career and pursued an unavailable man so that you don’t repeat this big mistake again.

***************Follow along on Facebook,  and Instagram. If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. Ha ha! I love how LW1 just “yadda yadda’d” starting an affair with her much older, married boss.

    Guess what LW1, if you don’t shit where you eat and only date available men, you won’t have to worry about “sparks” between your boyfriend and his wife or that his kids think you’re a homewrecking hussy. This is what we parents of young children call “natural consequences”.

    1. Seriously! I even wondered if a paragraph had been edited out or something. You’re just left to surmise that they started an affair, which is the whole reason she is writing in at all.

  2. LW2: it was never a relationship, you two were just friends with benefits. Now he’s got someone he wants to be in a relationship with. There’s a name for you if you stick around, it’s called: side piece.

    Don’t listen to anything he says, he wants to have his cake and eat it too! Watch what he does. Then walk away. Do WWS and block him. You deserve better.

  3. LW#1 — the daughter has reason to blame you for your part in the breakup of her family. You made a move on her father while his family was still intact. That you fear ‘sparks’ between a married man and his wife, suggests that you recognize that he is less than totally sold on leaving his family to be with you and has thoughts of returning to his family. If you felt your relationship with him was solid, you wouldn’t have this fear. Your tone suggests that he wanted a mid-life fling, but now that’s probably almost over for him and he prefers what he used to have with his wife, if he can get that back.

    LW#2 — you were vulnerable and he played you. Sex without dates puts you in the category of distant fwb, not any sort of deep emotional attachment for him. Live and learn.

  4. katmich15 says:

    LW2 – “How is this fair? Why would He do this? Is this his way of controlling what we have but have the cake and the pie at the same time?”
    It’s not. Because you let him. Yes.
    Dump this clown, none of what he says is true, evidenced by his actions. You deserve much better.

  5. Bittergaymark says:

    LW1). I’m nervous they won’t.

  6. PurpleStar says:

    LW1: Of course his daughter doesn’t like you. Heck, it is not certain that he likes you. You need to find another job, pronto. Healthcare is very insular – if your peers and his peers know of the affair it could be difficult for you find another job. He has a 25+ year history with wife, so even if the separation leads to divorce, they will always be entangled – children, grand-children – if you cannot handle that, and let him have the inevitable family time, then you need to leave the relationship before your jealousy and insecurity destroy whatever is left. And of course, you are jealous and insecure, because your know that this relationship did not start out above board. Because at some point, let me guess, his wife found out about you, and she put him out/he had to leave. This will not end well…

    LW2: What the frekkin hell? Are you going to continue to pursue this barely FWB man until he posts about his recent nuptials to the woman who he has announced to the world is “the one”.

    Both LWs – please work on your self respect and self care… Ugh, women like you two make me embarrased to me a woman sometimes.

  7. barrel_0903 says:

    So wanted to give everyone an update. I have cut all ties with this man. It was a struggle for few days. But You guys are right I deserve way much more. I went to the town to the local coffee shop and bumped into a long time friend. We talked for hours that day. we exchanged numbers and he has taken me out for few breakfast and dinners already. We decided to take it slow and friends only for awhile. Here is to me moving on and taking a leap again. Thank you everyone that has encouraged me with words to forget the idiot. has helped more than you know.

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