I am a woman CEO and hooked up with a guy the first night we met- he wants to join my company but I just can’t get over the way we met.


  • Don’t hire him. Especially if it’s gonna be uncomfortable in the long run. Unfortunately, sometimes the way you meet a person (regardless of how awesome he/she turns out to be) taints the relationship in the long run.

      • I doubt he would want to join my company if he didn’t respect me, and I wouldn’t consider it if I didn’t respect him. I just think that the close working environment of start ups – especially because it would involve travelling together- would just get complicated

        • He probably figures that it’ll be an ideal situation for him because he’ll be able to manipulate you to get promotions and power in your company and sleep with you whenever he feels like it; basically he’ll have the CEO wrapped around his fingers.

          • never thought of that- and it seems truly psychopathic but ultimately possible. I said that I don’t want to mix business with pleasure but he has pushed the business agenda ever since.

            I don’t feel like I am much of a pushover, if anything- I kind of feel like he has been working for free and trying too hard…

            • Nothing psychopathic, just plain old manipulation. All things equal, who would pick a work environment where they had more influence? Happens all the time. Sure, you’re no pushover, until you slip on the d!c( once more (and it’ll happen with such history +daily close contact)…

              • For such a long term and close working relationship, it would be pretty insane to go to those lengths for some extra power in the situation.

                Besides, with so many start ups out there, why create such a creepy work dynamic.

                Whatever his motives are (good, bad or otherwise), I just don’t want to deal with it

                • Good. There are plenty of other people that you can hire instead of him. It’s generally not a good idea to mix business with pleasure. Even if you can be professional about it, you can’t guarantee that he will be.

                  Maybe later on he’ll sue you if you fire him and claim that you did it for romantic reasons; like you fired him because he stopped sleeping with you.

                  Even if it’s a lie, you might lose the court case and have to pay him money even though you did nothing wrong. I would definitely advise against hiring this guy; you have way more to lose than you have to gain in this situation.

                  Like I said, there are many other people who can be hired in his place; you don’t have to hire him just to not feel bad, since he’s been pestering you about it.

              • I agree. It’s human nature to try to gain any advantage we can. Why work for someone who doesn’t care about you, when you can work for someone who you’ve slept with and who can possibly give you things because of romantic feelings.

    • “Don’t hire him because he will never respect you. How can you give him orders as CEO and be taken seriously by him?”

      Patriarchy speaks.

  • A woman here …

    Who cares if you had sex with him the first night or the 10th. The when is irrelevant. The fact that you both slept with one another could complicate things but it also depends on the maturity level of both of you. Sometimes people sleep with each other, so what.

    Do you want this to become a regular thing in sleeping together or a relationship of some sort? Then, no, don’t hire him.

    Is there a chance this will happen again? Don’t hire him.

    Can you be adults about this and it is what it is? Then, maybe, hire him.

    Just by vertu of asking the question I lean towards don’t hire him.

    • i am not sure if “being adult” or mature is separating what happened from the future- or just acknowledging that we crossed a line and it would be very immature to pretend that it didn’t matter

      • Think about it this way ,

        1.Is hiring him going to help he company? to what extent?or is he replaceable

        if he isn’t , be polite tell him he has competition and would have to fight for the job (use whatever system you’ll have to hire exceptions barred)

        Ask him why he wants the job , and what he can contribute that will eventually help to grow of the company.

        3.if you’ll have a good working relationship and can make sure it wont affect /hamper judgement for the company —- go for it (however talk to your co-founders about it)

        I think you want him on board , which is understandable but i wouldn’t hire him immediately (may be on part time basis so as to help you evaluate whether its helping the company or not)
        As long as you can keep it professional when working you’ll should befine

    • One night of passion has nothing to do with a business decision. If he’s the right fit and will help you accomplish your goals – you would be silly not to hire him. The key here is to never sleep with him again – or at least while he is employed by you. I think we can all agree that sleeping with your employees is a bad idea. What happened in the past is the past – all that matters going forward is your working relationship. If he is mature and you are mature – that should be fine. I would say if there is even one red flag (i.e. sexual innuendo or ‘inside’ jokes) – then don’t do it – but since you said he ‘pivoted’ your relationship to only business and is willing to work for free – well to me as a founder and CEO – isn’t that exactly the type of initiative you want? Any one who does this for me has a job instantly.

      • Agreed! If he’s the best candidate for the job, that should be the end all, be all. But be very clear about where the professional lines will be – and be sure not to cross them yourself!

  • Don’t sh*t where you eat.

    Can you be mature about this and work together? “Oh yes”, said all the people involved in messy/blowup work-affair cases.

      • And the lawyers went laughing all the way to the bank… And the CEO was fired by the board of directors… and she put out press releases that made her look even more ridiculous… tried to turn it around and say the employee was the one harassing her, but then there were recordings and no way around it… what could have been a promising career ended then and there…

    • Boom! Don’t sh+t where you sleep. That’s all there is to it. Help him find another job if you care and do (or don’t) sleep with him. He doesn’t have to be a part of your company.

  • The fact that you did this and that you’re now posting an inquiry on an anonymous website rather than answering the question for yourself tells me that you lack the maturity to hire him. If you’re going to run a company you need to develop better judgment.

  • Yeah definitely do not do it. Regardless of whether any of the scenarios with a termination/lawsuit played out, there is also the very-likely scenario that it comes out that “I banged the boss” could go down, either by him or by someone with knowledge, and that it fuels rumors that cause resentment for any view of unfair treatment. I’ve seen that happen a whole heck of a lot in banking.

  • So I told him “Absolutely Not, it’s not you it’s me and let’s just be friends”

    I realized from this thread that I need to trust my guy because even though I like working with him, it is a terrible idea for a multitude of reasons.

    Most importantly, it will fuck up our entire team if he and I have any kind of special relationship. And yes, I can let it go but one drunken celebration- or roadshow slip up and our whole ship could literally sink.

  • LOL.

    Sex always complicates things. Never fk your employee.

    I had a staff give me a blowjob once (obviously could do more if I wanted) and didn’t have sex with her because I wanted to keep things ‘appropriate’. Haha, yeah, insane as that sounds.

    Then, sometime later… a few months after she left the country, my other staff seemed to ‘ALL KNOW’ about it and were dropping hints to me, and laughing and etc. I finally demanded to know what was going on and they then asked me if I had sex with her.

    HUH!?

    And of course I plainly denied everything.

    Never touched another employee ever since. I work in a field where I am the only man and ALL MY STAFF ARE FEMALE, in close contact. Kind of hard not to do anything. (I can jolly well have sex with a good majority of them, to be honest, but I am not that kind of boss). I genuinely treat my staff as human.

    Quite a few staff likes me and that alone (without me doing anything to any of them) sparked off jealousy battles among the employees and I really hated to deal with that drama.

    Relationships and sex does not go well with work. In my opinion and experience.

    Seems that almost everyone gave the same answer. Which is not to allow him to join. Which is also what you already figured out. Interesting.

    • Apologies for this not starting as being directly on-topic for the original post, but I can’t pass this by.

      The post on “June 9, 2014 at 10:54 pm” says he got a blowjob from a staff member, but didn’t have sex with her? Have we learned nothing from Bill Clinton’s misadventure? In a personal relationship, sure there’s an enormous difference between intercourse and other forms of sexual contact, but in the professional world, sexual contact is sex, or else it’s harassment, whether in the court of law or in the court of public opinion.

      This is where it connects back to the original question, because if it gets out, accidentally or on purpose that you two had a past, you’ll have one court or the other to deal with, if not both.

      The other point that I haven’t seen brought up here for the original poster: There’s a reason why you and this guy aren’t in a relationship. It could be you, it could be him, but whatever the reason, what you had together didn’t warrant a continued connection. There’s nothing wrong with that in your personal life, if that’s what you want, but it may not speak to the two of you being together professionally either.

      Hope that helps, and whatever you decide, good luck.

  • So basically, YOU put yourself in this situation which makes you look like you have the morals of an alley cat, and now you don’t want to hire him? Oh well, he could ruin you if he wanted without being hired if he is savvy enough. Next time keep the legs closed.The tech world is too small, and I guarantee if he is in it, then your reputation will stained.

  • He respects me. I dont know lady. How long have you’ll been together. This is the easiest job he has probably chance of getting. I slept with the boss. So no chance of getting into trouble because ill just break her heart. Pls think with your business head

    Not your heart.

  • Humm it seems familiar to Jessica Pearson situation on Suits when she hires her boyfriend as a partner on the law firm..

    I also have the option that relationships and sex does not go well with work. But you are the one who will enjoy the situation and if something goes wrong you are also the one who will suffer. You deice what you want to do.

    Not enjoying the present because the future “can go bad”is not a good thing neither.

    So if you decide to hire him, please make sure all the proper paper work is in place to protect your company. If he refuses to sign the paper that is a red flag. And make sure you pay him well.

  • Don’t go there. Applying the gender-reversal test here, as a male. Thinking about hooking up with a girl who then asks to be hired. No way.

    There’s a really good reason you should never mix business with pleasure.

  • sex is sex and business is business. if he is not your husband/boyfriend you should keep distance. there might be too much trouble ahead.

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