I want to sleep with my boss; should I say something to him? (Sex Advice)

Hey Guys,

So I’m not usually a very forward person, but I’m about to change schools and I’ve had a huge crush on my boss ever since I started working. There’s an 11 year age difference. But I just really think, given the fact that I’m leaving, that it’d be fun to hang out while I’m still in town. I know that sounds so slutty, and you know what, maybe it is. But I never do stuff like this. I know sex is for love, but it can also be fun, can’t it??

Anyway, I wanted to ask him if he’d be interested in something like that, but given the age difference—I’m 19— and the fact that he’s my boss, I’m not sure how to approach the subject. I was just going to text him, but I’m just not sure. So I thought I’d ask you guys: Would a guy be into a girl being really forward and suggesting casual sex with no chance of any strings attached, even though there’s an 11 year age difference? Or does the age difference/work make it seem too inappropriate? If it does seem like something that I should go for, what’s the best way to ask? I’m not usually like this with sex and guys, but I figured, what with my leaving town soon and all, when else do I get this kind of chance, right?


Working Girl

Dear Working Girl,

Thanks for your question. This is pretty straightforward actually, at least from his point of view.

If he’s single, and attracted to you, it’s likely he’d be very much into your offer. The majority of guys would be, but not all. Some guys would have an issue with your age, or feel like they were “robbing the cradle” or taking advantage of you even if you were the one suggesting it. If you were in your 30s and going for a guy in his 40s it wouldn’t be a big deal at all, but since you’re at such different stages in life, the age difference is kind of a big deal.

That said, most guys would be happy to go along with your offer especially considering these few things:

1. You’re over 18. (He’s legally safe.)

2. You’re moving. (He doesn’t have to worry about many repercussions. Or be reminded that that he slept with a 19 year-old because he might be embarrassed by his actions.)

3. You no longer will be working for him. (It’s never a good idea to date or have sex with an employee. And probably against company policy.)

4. It’s your idea.

However, please think hard about this. Sure sex is fun, but connections that start off as only sex, often lead to confusion later. And since you really don’t know him at all—at least in this way—be careful. You need to use protection for one-night stands, or week-long stands, or with anyone you don’t really know. (That’s our paternal side talking.)

Now that we’ve given you the whole picture, the decision will be up to you. How should you approach him? First of all you shouldn’t be working there anymore when you do this. Just say this to him: “If you’d like to hang out sometime before I leave for school, give me a call.” If he doesn’t contact you then he’s either not interested, or not willing to risk it. However, we’re pretty sure he’ll take you up on your offer, although there are no guarantees of course.

Let us know if you have any other questions.

Take care,


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4 Comments on I want to sleep with my boss; should I say something to him? (Sex Advice)

  1. Kinda similar question, but worth asking.

    I’m going to college and there’s a guy I really like. We’re good friends often admitting things to each other and talking about sex on a subjective and nearly professional level. And I know he doesn’t think of me as girl friend or maybe even “sex material”, but I want him so bad. I’ve never wanted a guy on this level. In addition we’re both virgins.

    Unlike the post, were both 19 and another thing that complicates it all is that he knows me for being a devoted Christian (which is true, but my lust for him is so powerful and has been for a while).

    My question is that if I were to approach him and suggest that we have a one night stand, what’d be the chances of him saying yes? I mean, should I just buy a vibrator and be over with it?

  2. @Ariel…….If he’s attracted to you and doesn’t let his faith get in the way it’s likely he’ll take you up on it. Most guys wouldn’t turn down an offer of sex unless they thought it was going to get weird afterward. We don’t immediately afterward; we mean a guy will turn down sex if he thinks the girl will now be weird and clingy. If that makes sense. Our advice: Stay friends with him and let him make the first move. You can hint, but let him be the one to propose it.

  3. tasha williams // June 20, 2013 at 2:09 am //

    i need advice from you please. we have had this chemistry between us with this guy (ken) for the past 1 1/2 years then at some point we started fwb. i had a crush on him though. one time he told my bff the way he loved me and wanted us to date but i said i didnt want so i decided to ask him but he denied having said that. it hurt me but i decided to ignore that. so after a month or two i asked him what he thought about our relationship if it will ever be and he said we already are more than friends but we should talk in person. its been 2 weeks and the guy hasnt said a thing although i guess he is not i town but should i be worried or am overreacting? thanks

  4. @Tasha…….We don’t recommend FWB. It always ends up confusing someone and hurting someone. Case in point: You. We don’t see this going anywhere honestly. He may say he loves you, but actions speak louder than words. His inconsistency should tell you that he’s not as into you as he says. Sorry. Take care.

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