We’ve been dating for less than 2 months, we’ve kissed, and during the dates she shows interest.

I had noticed during the dates that she would often receive texts, look at them, smile, and then bring her attention back to me. I didn’t think too much of it at first, but after the first few dates, the way she was looking at her phone when she received the texts made me a bit suspicious as to who is sending her these texts.

So I genuinely asked her who is texting her, and she told me it was her boss.

Again, at first I didn’t think too much of it, maybe they just have a friendly relationship. Then after a few dates, and same thing happening over and over. I simply asked her if she only has a friendly relationship with her boss or if there were more to it.

She was honest and she told me they’re also dating. I simply said I understand, I was a bit surprised, but we’re not in an exclusive relationship yet so she’s free to do whatever she wants…

Now on hindsight, I don’t know if I should keep dating her if I’m looking for something serious.

**1) Even if we get exclusive, and she stops dating her boss, I wouldn’t be comfortable with her spending her day with a guy she slept with. So I would have to ask her to find an other job, and I feel like that’s a big request at the beginning of a relationship.**

**2) The age difference is quite huge, I don’t think she has big daddy issues or something, but like what the hell, 43 years difference….**

**In your experience, is it commonplace for a woman to sleep with a much older boss ? I’m not sure if I’m overreacting.**

35 comments
  1. If you’re not that comfortable with it, you’ve only been seeing her for two months. If she’s not really knocking your socks off nothing wrong with walking away.

  2. Damn *72?!* Are you sure about that? Also might wanna seriously sit down and reconsider the daddy issues part, cause she probably has plenty of those.

    In my experience as a woman who heard and saw plenty of crazy, *NO this is definitely not common*, sleeping with your boss or anyone who’s 43 years older than you! Unless there’s something benefiting her out of it, don’t even see a reason behind it, he’s like grandfather age.

  3. Wow. That’s down right nasty. You’re being way too chill about this. She’s got major issues.

    There is no way dude can even hit it right at that age. It’s either her getting special treatment at work, money, or she’s got such big daddy issues that she’s brainwashed by this geriatric dude.

  4. Always trust your gut instinct and listen to what your common sense is telling you.

    She is either doing it: 1) because she wants career advancement, 2) she is in the habit of sleeping with coworkers, 3) she likes convenient casual sex, 4) she is attracted to much older guys.

  5. Just let her go and move one. Even if you ended up with her why would she leave her job? If she stop seeing her boss what’s gonna stop her to get in another situation like this in the future? You? I don’t think so. The fact that she is still dating the boss let me know that you aren’t really her priority my dude…

  6. “I don’t think she’s got daddy issues …”
    No … she’s got grand daddy issues

  7. Honestly some girls go to great lengths for money I’d say leave her bro before your broke when he’s floating down the river

  8. As a woman, I am telling you run. I can’t fathom her interest in her boss is more than her looking for a leg up career wise or other financial gain. But if it’s more than that and she has honest intentions with this man, why bother competing with a guy she spends a lot of time with already? Either way something is of with her “situationship” with her boss. I find it awkward to be in a relationship with someone you work with, let alone a 72 y/o when I’m not even 30.

  9. 42 M. As you said, unless you’re exclusive she can date others. But I’d bolt. Fact is she’s going to be more inclined to stick around him because he can influence her career. I’m so sorry.

  10. I stopped reading after the first few sentences. Anyone who looks at their phone several times on successive dates just isn’t that into you. Full stop.

  11. Possibly her sugar daddy. But could also just be sleeping her way up the chain, I would recommend you find someone else to be with, the only good thing about this is that she was comfortable enough to be honest and tell you what she was doing.

  12. Leave her eating old meat with that dude, it seems she prefer the old ones (suggar daddy’s) so leave her, you deserve someone better. No that type of “woman”.

  13. My dad is in his 70s and more often than I care to know he gets a lot of young women approaching him at the bar he regulars at.

    Youngest girl was 19 that was a relative to another regular and was from out of town. Tried super hard to get my dad. Made sugar daddy comments, sexual advances, etc. though sure I’ll joke with him and tell him release that young tiger instinct he has locked away, but he doesn’t have the energy to entertain them.

    My dad retired with a lot of money and a lot of free time. Worked as a plant operator for nearly 50 years at the same company and even gets paid by the company to help with small stuff even from home. And everyone that knows him brags about him because he’s a well liked person.

    Sometimes I ask myself if I’m adopted because i sure as hell didn’t get any of his mojo.

  14. Brother, it’s a red flag. Get out out before you get even more attached and it’s harder

  15. It’s not common. Ask yourself if you would want a wife to do these things. If no, she probably ain’t it.

  16. Mmm, it’s a bit sketch. 72-year-old. She’s not dating him. She’s surviving from him. And honestly, you’re just going to be her option.
    If she’s still dating him, just let it go. Cause she’s not gonna stop. And no way she’s quitting her job.

    Well, tell her how you feel and tell her what your intentions are. And watch her reactions, that will tell you if she’s willing to leave that lifestyle or stick to it. Then you know you’ve given it a shot and you can make peace with yourself.

  17. If he was in his 30s, would you feel any different? It’s always a gut punch knowing the girl you’ve been seeing for several months is also seeing (and having sex with) someone else – especially if she is having sex with you.

    I’ve found in my experience, that when someone is “dating” multiple people, they’re usually not overly enthusiastic about any particular one. Maybe they see each person for a different reason. But when they meet someone who they really like, they tend to lose interest in the others after a month or two.

    Again, just my experience.

  18. Whenever I read stories like this it always amazes me how anyone could be in this type of situation and not know what to do.

    There is no other answer but to cut things off because the more invested you become in this woman, the more its going to hurt when it INEVITABLY fails horribly.

  19. I mean, sure, she’s still tehically single hence free to do so….but, you prolly don’t want to be her “option” and that is, against some 72yo dude, that she’s likely using to atleast some degree..which also tells about her character. So, ye…If i was you, i’d either stop seeing her completely or perhaps just switch to seeing her as something casual.

  20. Ok so just imagine his 72yo wrinkled little Jimmy going into her… ? It’s just a no-go zone from that point on. That’s really a hard pass. Side note I really don’t understand women who do these things. Imagine a young dude having sex with a 72 year old woman and being open about it ?!?!?!? How are women allowed to do these things… Hard pass (again).

  21. If you date her then don’t be surprised when it goes down hill chick 29 dating a 72 year old tells you all you need to know. Good luck if you wife that.

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