29-year-old receives job and accommodation from boss, starts secret relationship with her 22-year-old son and doesn't know how to tell her she is pregnant with his baby after he passes: 'I feel like a traitor'

Author image for Ally Perry
Ally Perry • Writer and Editor
Jan 30, 2025 6:00 PM EST

No matter what we might like to think about ourselves, none of us are above getting into a situation that may best be described as 'messy'. Even if we try our hardest to keep our lives in order, there is no predicting the weird and not-so-wonderful things that other people or simply the cruel hand of fate might bring to us. In these cases, the best thing to do is attempt to think logically and deal with the fact that navigating the near and possibly far future is going to be more difficult than we would like it to be. 

This is especially true when it comes to family issues. More often than not, they are the kind of problems that simply cannot be avoided, and have some pretty bad ramifications if they are. Difficult it may be, but it is important to face the issue head-on even when you might be in the wrong.

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  • 01
    Cheezburger Image 10461174016
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • This is exactly what one woman worried about when she discovered that she was pregnant and her boss's late son was the father. She had become great friends with her over time and the manager had even previously provided her with a place to stay and some extra work when she was struggling to get on her feet. However, she had never told her about the relationship and was worried about how she would react to the truth.

  • 02

    My (29f) boss/best friend's (45f) only son (22m) passed last week. I'm pregnant with her son?

    I'm having mixed emotions in this whole situation. I feel like a traitor, like I stabbed her in the back for sleeping with her son. At the same time I really cared about him and I loved him. I wanted a family with him and we were seeing each other for about 9 months (officially) already. I've known her for a little over 2 years and she's helped me get on my 1 feet.
    via throwraLonelyw
  • 03
    I work for her business and I now manage all the employees. I started off living in my car and she gave me a place to stay while I made some money to find an apartment. After that she started giving me more work and even started giving me some work at her home. She trusts me completely and I guess I broke that trust by seeing her son without her permission. I have mixed feelings because I did things the wrong way, but at the same time I treated her son like a king and I know he was happy with me
    via throwraLonelyw
  • 04
    She trusts me completely and I guess I broke that trust by seeing her son without her permission. I have mixed feelings because I did things the wrong way, but at the same time I treated her son like a king and I know he was happy with me before he left. She has no idea about our relationship we had and we were gonna tell her, but life took a bad turn. I know he left before his time because he had many great things coming and now I have to raise our child with him absent. When is the right time
    via throwraLonelyw
  • 05
    TLDR: my best friends son past away in an accident.i was secretly seeing him and im having his baby in a couple of months. Edit: I forgot to clear things up, she knows im pregnant, she just doesn't know who the father is.
    via throwraLonelyw
  • 06

    Some people wanted to offer advice, and others judgment.

    NYCStoryteller I'm sorry for your loss, and for hers, and for your child who will grow up without its father. Her son was old enough to make his own life choices without his mom's "permission." However, it is kind of messy to secretly date your boss's child. I would tell her that you lied to her about not knowing who the baby's father was because you were scared about her reaction, and you need to apologize for that. Tell her that you would be glad to give her some space and time to process, and
    via NYCStoryteller
  • 07
    mkate 1999 I would've been waiting till the son was OK telling his mom too. It was a joint effort. I'm sorry for your loss, OP. I hope it works out.
    via mkate1999
  • 08
    GraceOfTheNorth I don't know why there is an expectation that the boss will be mad. One would think she'd be ecstatic.
    via GraceOfTheNorth
  • 09
    NYCStoryteller I would be mad if someone that I had given a job and considered a "best friend" in spite of a substantial age gap spent over a year dating my child in secret, and then after he tragically died in an accident, told me that, by the way, I'm pregnant with you child's only baby. She may be happy eventually to know that some part of her baby boy is still out in the world, and she may forgive OP and keep her on staff and have a good friend/grandparent relationship with her and the baby,
    via NYCStoryteller
  • 10
    Its-Just-Whatever Wow, this is a heck of a situation and I'm sorry for your loss, honestly. I'm not sure what the root problem was for her, she clearly respected and cared for both her child and you. Logically, I would think that she would be relieved and happy to have a grandchild from her recently lost son, but I don't know all the details here. You might as well let her know now, assuming you're far enough along in the pregnancy to communicate that. Ideally, the two of you can work as a team
    via Its-Just-Whatever
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    throwraLonelyw OP I hope she's happy about it. I love her and I loved her son so much. If she would have approved I think I would have married him eventually. It's been tough, but I at least know I'll have a reminder from him. And yeah I am more than halfway along the pregnancy, I just have been holding his mother off on knowing he's the father. She's excited for my pregnancy she knows that, but she doesn't know it's his baby.
    via throwraLonelyw
  • 12
    Its-Just-Whatever Do you know why she didn't want the two of you together??? Outside of her resistance this seems like a good situation initially.
    via Its-Just-Whatever
  • 13
    throwraLonelyw OP She didn't actually say that ever. I just thought he was off limits since I'm her best friend and that's her son.
    via throwraLonelyw
  • 14
    Its-Just-Whatever Oh my gosh, that's even better. You might be in a situation where an awful scenario can be given a silver lining by just using some direct communication.
    via Its-Just-Whatever
  • 15
    Ambitious-Lettuce-48 I'd tell her soon. Let her have time to process the situation so she is ready for it by the time the baby comes. She has every right to know her grand baby, especially considering her son has passed away and this is her last connection to him.
    via Ambitious-Lettuce-48
  • 16
    LastCut3224 Make sure when you confront her that you bring proof. Any photos you had. The stuff he left at your place. Screenshots of text and the ability to show her the text. Lastly you need to tell her that you understand if she doesn't believe you and offer a prenatal DNA test against her DNA to prove that it's his child.
    via LastCut3224
  • 17
    throwraLonelyw OP I do have a lot left from him in those terms. I have a lot of photos of us, I have texts, and gifts he used to give me and stuff I gave him.how work I be able to get a dna test so she could see it'a her grandchild?
    via throwraLonelyw
  • 18
    Brined Brittanica do you have enough money saved up in case you lose your job?
    via BrinedBrittanica
  • 19
    throwraLonelyw OP I have money saved. I made some investments while I had the chance.
    via throwraLonelyw
  • 20
    PrudentConstruction3 This is so inappropriate on so many levels... she's your boss and also your friend and also helped you out by giving you a place to live and you went ahead and banged her son who mind you is still fairly young kept it a secret from her and then also got pregnant by him? Where to did you think this was going? You're effin 29 not 16 how dumb are you?
    via PrudentConstruction3
  • 21
    violue Give it a few more weeks. She is not equipped to deal with that kind of news right now.
    via violue
  • 22
    Clamps11037 She's your best friend but you kept it a secret you were sleeping with her 20 yo son when you're almost 30? And she gave you a job and place to live. Don't be shocked when she doesn't take the news well
    via Clamps11037
  • 23

    In the end, she came clean.

    Edit 2: I talked with her last night after we had dinner. I apologized for hiding it from her and I told her I didn't want any money or anything from her I just wanted her to be able to enjoy her time with her grandchild. I was honest with her on how our relationship started and how much I loved her son. She had her doubts about it and told me she knew something was up between us 2, but she didn't say anything because she wasn't sure and she didn't want to make assumptions. She was very upset at
    via throwraLonelyw
  • 24
    I showed her pictures of us together, places we went, our messages, and she broke down crying. She looked very upset and I genuinely thought she was going to hit me because it looked like she was about to slap me. She asked me to leave and give her some space. I left home and she called me at midnight and asked if I could come back and spend some time with her. We finished talking and I offered her to take a dna test so she could see it's her grandchild. She believed me on what I said but she to
    via throwraLonelyw

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