Casually drop hints that you are suffering from STDs, that’ll get him to back off
Yes I am which is why you should have read the read of the sentence which was “or quit or file a lawsuit”. Mrs Cad was refused promotions at a very large company she worked at because she refused to sleep with the head of her division. She chose to find another company and quit which is extremely difficult when you are leaving a company as large as hers was. Some women may opt to move up on their backs but I didn’t say the OP had to now did I?
I feel obliged to point out that from a legal perspective, this is not actually the standard for sexual harassment.
Y’know, I don’t think chatting about politics is a really good idea, either. Too much potential for disagreements to become heated and ugly.
Also, you can be trustworthy in your job performance without being his best friend outside of the office. Be reliable, get the job done, be the one who bails the company out in a work-related crunch-time or emergency. None of this requires you to be his shrink or put up with hearing about his bubble baths.
I agree with documenting everything, just in case. And redirect, redirect, redirect. My impression from what you said is that he’s a bit clueless about appropriate work boundaries rather than actively malicious, so it seems a good bet that he wouldn’t take gentle reminders too badly. I wouldn’t be indirect about it, but you can still be nice, mostly with keeping a neutral tone of voice. “This is not an appropriate topic for a workplace, let’s get back to work.” vs. “THAT WASN’T APPROPRIATE!!” Treat it like imparting information he was lacking (where the boundary line is) rather than as a mortal offense.
I wasn’t speaking legally (otherwise I’d have said de jure :D) - I was just saying from a sensible human interaction POV. The only exception (in a not very multicultural environment anyway) to this rule would be if the OP were crazy, which she isn’t.
Unfortunately, I think much of the advice on this board is more geared for corporate dronery working at a large anonymous megacorporation. “Contacting HR” or “documenting everything” really only matters if you work for some mid-level functionary who is at the mercy of a large company’s beurocratic performance evaluation processes. Or if you plan on a sueing them and want a record.
For your situation, since you are working for the CEO in a small startup, you are better off defining the relationship the same way you would with a normal person you couldn’t just blow off for whatever reason. IOW, you want to be friendly, but avoid giving mixed signals. You want to be firm, but without being offputting or hurting his feelings.
Like you don’t want to be like “that’s inappropriate” because your boss may feel he decides what’s appropriate in his workplace. But by saying “I don’t really feel comfortible with that”, you are giving your boss the opportunity to not be a dick by continuing to discuss something that makes you feel uncomfortible.
Also, is there a chance that you are blowing this up in your mind? I’m a pretty chatty, funny guy and girls seem to respond to that. But just because I’m friendly doesn’t mean I want to sleep with them.
For who exactly?
Department of Labor, and/or her lawyer, figuring that there’s a non-zero chance that she may want to pursue things legally later if addressing it herself does not have the desired effect.
Better to have it and not need it than need it and not have it.
To be fair that pretty much dooms her into never working for a similar startup again.
I have a theory here but don’t feel like starting a thread about it. Basically because of the board makeup, most posters here are going to be in academia, government jobs, or “easy” drone type corporate things, probably to a far greater extent than the general population. This is because the alternatives (i.e. small businesses) either require you to be an entrepeneur which while you can totally be one and a liberal (in the american sense) is negatively correlated, or to be foolish regarding work (if you are a minimum wage type) because of the crappier benefits, lesser working-up-the-corporate-ladder-type opportunities, or the other reason to work in a small business, the informalness, which basically needs a family/loyalty type orientation which for Haidt reasons (and reading Haidt is how the SDMB has transformed my life) is mostly conservative.
Huge generalisations of course but I am sure that they will hold.
How silly.
Plenty of engineers, doctors, and many other types on the boards. There is nothing which means that if you’re an entrepreneur you are not going to be liberal, and even less for people who work for small corporations. There are a wide range of occupations and to broadly toss everyone into a pile of clueelessness is insulting and says more about what you read into the board.
[/hijack]
For the OP, since he’s responded appropriately in the past to when you’ve said something makes you feel uncomfortable then why not continue that strategy?
If he’s harmless, then he’ll quit. If he’s not, then you’ll know and you can take it from there.
If someone is going to hold being sexually harassed against her, I’d guess she probably doesn’t want to work for them anyway. I wouldn’t – it would say a lot about their culture.
Not a corporate drone, btw. I work in the arts. My “day job” is freelancing.
But isn’t it strange that he would feel that comfortable around a woman he’s only met once and has only known for a few months?
I should mention I’m not the only employee he chats with multiple times a day. I’ve never asked my co-workers if he says inappropriate things to them during their chats, do you guys think I should ask the co-workers I’m closest to?
Yes. It’s very likely he’s like this with everyone. Some confirmation that he is would hopefully put your mind at ease.
I doubt that. Really there are so many companies and “startups”, unless the OP is someone really well known in her industry, it’s not like any other company will know who she is.
Well, do I think for whatever reason, the board does skew towards academia, information technology, and a lot of low-level corporate jobs. I don’t see a lot of Wall Street types or high powered lawyers or corporate executives. There are some, but not that many.
Realistically, for the level of “harassment” the OP is talking about, a lawsuit would be a time consuming, expensive waste of time.
I agree that at the current level a lawsuit isn’t appropriate. Also given her goals. I would be documenting things in case the situation changes.
Suppose he shifts from being mildly inappropriate to being more suggestive? Suppose he starts pressuring her for sex, and she declines? Suppose he then starts punishing her for that.
Then she’s going to want a record of his behavior. Especially if she wants to leave but can’t get a good recommendation from him for her next job opportunity.
I think the appropriate response at this point include documenting things and trying to shift the topic politely whenever he makes you uncomfortable, perhaps with a comment to that effect. “I’m not really comfortable when you talk about…” rather than “STOP THAT!”
Talking to other employees about how he relates to them might be useful, depending on how well you know them. But could also start rumors that would get back to him, if those employees are not discrete. Tread carefully.
So I took a chance and contacted one of my co-workers whom I am fairly close to.
It turns out he overshares like this with ALL of his female employees. She says he is emotionally immature and insecure, and is drawn to women because he feels he can emote to them and push their boundaries more easily than his male employees. Occasionally his wife gets pissed off at him and throws a fit because he ignores her needs, and then he complains about her to the female employees. (I’m speculating here, but she’s probably tired of being his mommy for almost 20 years.)
However, so far none of the female employees have had to deal with unwanted sexual advances or physical overtures. Apparently he just likes having these little emotional affairs with them, and they deal with it by setting boundaries and gently (sometimes firmly) reminding him of those boundaries when he says something inappropriate. He’s always responded to these reminders, as far as she knows, and gradually the women have trained him to stay within their boundaries for the most part.
So, there you have it. Looks like he doesn’t want to sleep with me after all, and I just need to be firm with him. Like a mother. 
I’ll see how much of an emotional toll setting these boundaries takes on me, and I will be periodically re-evaluating my decision to stay with the company. But for now, at least I have a way forward in dealing with these issues.
Just thought of this last night although it may be effectively impossible in a company of 16.
The OP should find out the Bossman is like this with the other employees. Does he offer the men a night out smoking a blunt while watching the game? Does he talk about his wife to the women in the office? Does he have any other gossip buddies? If so then it is clearly a boundaries issue; otherwise it may be all about you.
ETA: How did I miss that last post?! :smack:
That sounds like a good plan. I have to tell you, though, my initial response in reading your post was, “Jesus Christ, would you just grow up already, man?” I would have no interest in babysitting this guy, but I’m not you. 
Haha, I know it’s not for everyone. But if you got paid six figures to work 40 flexible hours a week from home doing challenging, interesting stuff, you might have a slightly different opinion.