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January 5, 2013 8:58 PM   Subscribe

I haven't had sex in more than three years. I am going out of my freaking mind. One of my New Year's resolutions is that I must end this dry spell. I have a friend with whom I would like to start sharing some benefits. How do I go about this?

Straight lady here. Even though I greatly prefer relationship sex to one night stands, I don't want to start a relationship right now. I am too busy, and I don't want my life plans to be derailed by a boy. I think friend-sex is the way to go for me and I'm uncomfortable with casual sex with someone who is not a friend. (Done it before; it was not at all satisfying even though it was fun, safe, and I don't have any hangups about having done it.)

So I've become friends with a guy to whom I'm really attracted. I like him as a person and as a friend, and though he is perhaps not conventionally attractive, I find him so freaking hot I want to tear his clothes off and ravish him on the tables, the floors, anywhere, everywhere, every time we talk.

He is not "relationship material". He's 15 years older than I am (I'm mid 30s, he's late 40s). He describes himself as a "confirmed bachelor"; as I understand it his previous relationship ended because she wanted to get serious. In fact, according to my definition of "serious relationship", he's never had one (he thinks he has, though). He doesn't want kids and I do. He can't leave the area, and I have to. He's white and I doubt he's ever dated a black girl, which I am. His school district wasn't even integrated when he was a kid. (He's not racist, at least not any more than the average American, including myself, but according to him, his family is.)

Oh, and he's my boss. He doesn't supervise me, but I ask him for advice and he could, for example, get me fired if he wanted. He would never do this -- he's mature enough that his ex is still a regular customer, for example. But if I stopped working there, it wouldn't be the end of the world. I'm part time and not dependent on the job and would just devote more time to my business.

So overall, he doesn't actually work as someone I really want to date, and I'd probably be over him already if I were looking for "the one" as opposed to "right now". But his unavailability actually makes me want him more -- there's a huge appeal to the ease of cutting ties while remaining distant/casual friends when I move away. And he is so hot. It seems like a win-win. He gets to bone a younger woman with big tits who doesn't want to commit to him -- what's not for him to love about this situation?

Also, I should add here, I think he is attracted to me, but there has been no overt confirmation (no kissing, etc). I do know he likes me as a friend. We hang out outside of work, just the two of us, every other week or so. At work, we're pretty professional; in fact, I've noticed that the more people are around, the more he avoids me. For example, if I'm sitting somewhere, he might come hover and start a conversation with the person I'm sitting next to, but he won't sit down until I leave. But if it's just the two of us, he'll come sit right next to me.

Outside of work, we hug regularly, and have come close to snuggling (it was awkward). Then there was that one time when we briefly held hands (more awkward than anything I've experienced since middle school). I cannot imagine he would make the first move under any circumstances. Even though I feel I've made it clear that I'm attracted to him (though I have perhaps also sent mixed signals accidentally), I think he would worry about being inappropriate. Also, he knows I ultimately want a serious relationship and kids (because before I wanted to sleep with him, we had a few amazingly good serious conversations, which we still do.) Since he's older and was conservatively raised, I'm afraid I'll turn him off by being too direct. I can't even imagine inviting him over to my place because I feel like he would worry about it being inappropriate. We've always hung out in public.

He's an alcoholic, though he's been sober for years, so the no-fail move that's started all my relationships -- we both get drunk and kiss -- is out. I rarely drink these days myself anyway.

So, how the heck do I make this happen? Should I have a conversation with him or just kiss him? Would it be best to bring up the subject/make a move before one of our times hanging out, or at the end? What would I say, either before or after we kiss? I don't find guys I want to sleep with that often these days, and I'd hate to mess this up, because like I said, I *really* need to get laid.
posted by anonymous to Human Relations (38 answers total) 5 users marked this as a favorite
 
Oh, and he's my boss.

No.
posted by cmoj at 9:11 PM on January 5, 2013 [100 favorites]


He gets to bone a younger woman with big tits who doesn't want to commit to him -- what's not for him to love about this situation?

I know that you will get a ton of other advice so I just want to say something about this. Society tells us that this is what all heterosexual men are desperately drooling for, but that is decidedly not always true. If you go into this situation assuming that it is true, you could end up with a whole lot of negative consequences, including feeling extremely hurt, humiliated, and rejected if you get turned down. Or if he has sex with you once and then turns you down after that. Even among guys who are up for casual sex, I think it's way, way more common that they prefer a one-and-done type of thing, rather than an ongoing thing, and I think a lot of women get confused by that.
posted by cairdeas at 9:19 PM on January 5, 2013 [21 favorites]


Oh, and he's my boss.

There are 6 billion other people on earth for you to fuck who cannot cause you to lose your job. Pick one of them.
posted by elizardbits at 9:19 PM on January 5, 2013 [47 favorites]


So, how the heck do I make this happen?

You get a new job first.
posted by dekathelon at 9:24 PM on January 5, 2013 [17 favorites]


and have come close to snuggling (it was awkward). Then there was that one time when we briefly held hands (more awkward than anything I've experienced since middle school)

What makes you think that escalating the physical side would render things less awkward? Usually if touching someone feels strange, kissing them or fucking them feels straight up wrong. In my experience, anyway.
posted by Sara C. at 9:44 PM on January 5, 2013 [5 favorites]


Oh, and he's my boss.

I read this and read no further. It seems that everyone else upthread had the same idea. NO. Not an option.

Lady, you want casual sex and you are in your mid 30's. The number of possibilities open to you is ridiculously gigantic. My friend was just telling me that she used a phone app where she could literally find men in her area to have immediate casual sex with in a bathroom. (I know she was trawling Ashley Madison for hookups, though I don't know if that was the app she used or not. Memail me if interested and I can do some sleuthing. This particular friend of mine is a sex fiend, you may or may not want such casual sex but the point is it is very easily available.)

Do. Not. Have. Sex. With. Your. Boss.
posted by kellybird at 9:46 PM on January 5, 2013 [9 favorites]


I'll add that, from what you describe, there doesn't seem to be any sexual tension between the two of you, and you don't go into a lot of detail about how you know he'd be attracted to you at all.

It just sounds like this is somebody you have no chemistry with, who you have little compatibility with on the level of sex, who it would be inappropriate for you to sleep with in the first place.

Why go there? Do you not know any other single heterosexual men at all? Is there no way for you to meet one who might be a slightly better fit?
posted by Sara C. at 9:47 PM on January 5, 2013 [3 favorites]


Find someone on Craig's List or OkCupid. It won't be hard at all. This is waaay too much drama and overanalysis. It also seems pretty clear that you have some strong feelings for this guy. Nothing about it says "no strings attached".

btw: not all guys are looking for NSA sex with women with large chests. This is part of the lie we are led to believe.
posted by bearette at 9:47 PM on January 5, 2013 [3 favorites]


From the OP:
I wrote in the post that the guy is my boss; I apologize, but I oversimplified when trying to anonymize the details of this question and left the wrong impression. He is senior to me, but he doesn't supervise me and how this job is more something I do to pass the time, not for money. He is in a more senior position. However, I could easily quit tomorrow. I could quit before I talk to him, and it would be no big deal whatsoever, for me or him. I don't think this is necessary, because the job is fun, and he's proven to be mature about this sort of thing. All I wanted to convey is that because of his senior position relative to me, he may be hesitant to broach the topic with me.

Also, because of the nature of the job, he can't get into any professional trouble if he dates me, whether or not we work together. Again, I am sorry to be so vague about the details of our working relationship, but I have a pretty unique working environment and a pretty unique job and would be easily identifiable to my friends if I explained exactly why this isn't exactly a job and he isn't exactly my boss. I apologize for using the word "boss" and see how it's misleading. It's not accurate, except in the most simplistic sense.

Again, I just want to clarify that he's senior relative to me in many ways, and I feel that contributes to why he would be hesitant to make the first move -- it's not about employment per se.
posted by restless_nomad at 9:47 PM on January 5, 2013


He describes himself as a "confirmed bachelor"

confirmed bachelor: Polite euphemism for a gay man
posted by lamp at 9:47 PM on January 5, 2013 [20 favorites]


Relations with coworkers are fraught enough... But with a boss type person? From both sides it should be "hell no!"

I'm a boss, even if I was single and found an employee attractive no way in hell would this happen.. No... Figgen...way. Prob specfic policies against it as well that could endanger both your jobs
posted by edgeways at 9:48 PM on January 5, 2013


even if he is not your "boss", there are tons of other reasons not to go there.
posted by bearette at 9:49 PM on January 5, 2013


he's proven to be mature about this sort of thing

How is that? You haven't actually slept together yet. You haven't kissed. All you know is that he behaves somewhat like a rational human when you are both at work around other people. Which is a pretty low bar to set for "no, really, I could sleep with a superior".

Also "no, really, I don't even need this job that bad" is a very low bar to set in answer to whether you should sleep with a coworker who is superior to you and who could make your life miserable if things didn't go well.

Look, I have "don't shit where you eat" temptations of my own, from time to time, and I'm single and in my thirties too, so I get how you're feeling. But seriously, this is a superbly bad idea. From top to bottom. Nothing about this sounds like a good idea at all.
posted by Sara C. at 9:52 PM on January 5, 2013 [2 favorites]


Listen you say that he's a confirmed bachelor which = "I don't want a relationship" and the boss situation is irrelevant and you aren't looking for a relationship. Just tell him straight up what you want... remember you aren't starting a relationship and he's cool with this kinda thing right? The only thing you have to lose is a nice evening or an awkward rejection. And the job isn't a big deal anyways. Basically all you have to say is "Hey want to go have some fun with me sometime?" Be safe.
posted by Brent Parker at 10:05 PM on January 5, 2013


I'm going to be the first here to actually answer her question instead of saying it's a bad or good idea. What you could do is on one of those occasions when you are outside of the workplace with him, tell him what you want to do in general (not specifically related to him) and either see what he says about it or ask him what he thinks about it. See where that conversation takes you - it may provide an opening.
posted by Dansaman at 10:09 PM on January 5, 2013 [10 favorites]


One other point is that whether he's your boss or not, he has to be very careful making any moves toward you when you both work for the same company due to the hell that comes from a sexual harassment complaint if things don't work out - another angle on the "don't sleep with a coworker or boss" advice, which is spot on.

The phrase "confirmed bachelor" would make me think twice about the possibility of him being gay, also. Don't think you'd be the only one who never dreamed such a thing. When you also mention that you both felt "awkward" when you touched the bare edge of personal intimacy, that pretty much seals the deal.

A gay man can be the best friend you ever had, but if you're sexually attracted to him, you'll both be uncomfortable. You need to find a man to get your mind off this guy and take care of your sexual needs - then maybe you two can continue to be great friends.

Others here have good ideas about where to look for a partner for casual sex. Good luck to you.
posted by aryma at 10:15 PM on January 5, 2013 [1 favorite]


Good grief, did anyone read the whole question? Anonymous, I suspect that he is assuming that a black woman would not be attracted to an older white dude. You're going to have to make the first move (just kiss him.) And he'll still probably be incredulous and kinda nervous about accidentally offending you somehow.
posted by desuetude at 10:21 PM on January 5, 2013 [5 favorites]


It sounds like you really have a crush on him, even though intellectually you know things wouldn't work out for a serious relationship. You're putting an awful lot of thought into this. I'm just saying, maybe you should look for a situation in which you're less inclined to be emotionally invested.

But, if you want to proceed, how do you make this happen? Just kiss him. Pretend you're both drunk.
posted by J. Wilson at 10:26 PM on January 5, 2013 [1 favorite]


Oh, and he's my boss.

Also, because of the nature of the job, he can't get into any professional trouble if he dates me, whether or not we work together. Again, I am sorry to be so vague about the details of our working relationship, but I have a pretty unique working environment and a pretty unique job and would be easily identifiable to my friends if I explained exactly why this isn't exactly a job and he isn't exactly my boss. I apologize for using the word "boss" and see how it's misleading. It's not accurate, except in the most simplistic sense.

Employment lawyer here. Of course there can be plenty of trouble for everyone. My job is cleaning up after these messes. And they are often quite messy.

My advice is straight up, don't do this.
posted by Ironmouth at 10:27 PM on January 5, 2013 [14 favorites]


If holding hands and almost cuddling were awkward, WHY ARE YOU THINKING SEX WILL BE GOOD?

It will most certainly be awkward. Drop this current plan.

Listen.

I was mid-30's not too long ago, and unmarried. I now have a husband and child.

These years fly by. Unless you are planning to adopt (and also if your as-of-yet-unmet-future-husband is OK with adopting) then you kinda have to start dating NOW, but for real.

You can also do OKCupid, make friends, then sleep with someone casually, but regularly.

This guy does not sound into you, at any rate.


It really seems like you are putting off a "real" relationship. Which is fine!

You'll send less "mixed signals" if you sort out what it is you truly want. You are so confident right now, you don't see how contradictory your stated desires are. If I can see it, so will potential partners at whatever commitment level you are seeking.
posted by jbenben at 10:36 PM on January 5, 2013 [5 favorites]


Desuetude, I read the whole question. It sounded to me like the OP was layering on a lot of interpretations, but what's underneath doesn't equal he is interested in her romantically. What did I miss??
posted by jbenben at 10:39 PM on January 5, 2013 [2 favorites]


Good choices are seldom made out of a desperate need to bang, but then again life is too short to make good choices.

You're approaching boner-killing levels of overthink, though. So basically you have to get him alone and be all, "nice shoes, wanna fuck?" ASAP, or nothing will ever happen.

CAVEAT: he will say no, though, because all actual real-world signs point to this ain't happenin'. The lady (you) doth protest about 500 times too much for this to actually be a promising situation on any level.
posted by like_a_friend at 10:55 PM on January 5, 2013 [2 favorites]


Let me reiterate... Confirmed Bachelor means gay as fuck, and still in the closet officially. Not yours, under any circumstance. Hit up fetlife if you want to screw the brains out of someone who's the boss of you locally and safely.
posted by Slap*Happy at 11:02 PM on January 5, 2013


Should I have a conversation with him or just kiss him?

I vote: conversation.

There is a running advice-meme here on AskMe of "just kiss him!", but I think it's more respectful to first make sure there are strong signals of interest, built up over time, before getting all up in someone's face. A lingering touch or glance, increasing physical closeness, etc.

Lurching in for a surprise-smooch to force the issue just seems a little...ham-fisted. (I made that mistake once, and the guy's OH HELL NO face taught me a lesson, all right. Yeesh.)
posted by nacho fries at 11:16 PM on January 5, 2013 [4 favorites]


Why don't you ask him out the next time you're hanging out outside of work, if he says yes, wear something sexy that complements your boobs and while you're out let him know what kind of relationship you want without saying you want it with him and see if he's amenable. (If he's not interested in your boobs he's gay.) If he's interested in such a relationship with you, I think he'll let you know.

If he says no to going out, move on.
posted by shoesietart at 11:22 PM on January 5, 2013


This sounds like it's fraught with more drama and messiness than an actual relationship. Why would you want to do this?
posted by loriginedumonde at 11:29 PM on January 5, 2013 [16 favorites]


Let's take the whole boss thing out of the equation and pretend he's your average joe. It was awkward trying to cuddle with him, and it was awkward holding hands. Where's the sexual chemistry? Why go through all the trouble of figuring him out when it'll probably lead to "we kissed and it was awkward."
posted by Autumn at 12:14 AM on January 6, 2013 [4 favorites]


Why not be straight up honest with him. I find you incredibly attractive. I am not looking for a relationship either. I am however looking to get laid. We you be interested in exploring the possibility of a FWB relationship with me? Starting tonight.

See what he says. From the sound of it, I don't think he is gay as you mentioned his ex is a client. Unless she is a he, the implication is that his ex is a she. Because he is either longer tenured or higher up and about 15 years older, he will likely never make the first move. But if you are explicit with him about what you are seeking, I think you will be fucking him before the end of the month. Don't worry about the awkwardness of holding hands. Some people are just not hand holders. I was married to one for 18 years. She did not like holding hands, but she did like to get laid.

The only concern I have is that while you don't care about the job, he may. So while you are willing to live with the consequences of whatever happens if it happens, he may not. I would either ask him during the above conversation if that is an issue for him or, if it happens that you get together, after you are both finished your business and right before you are going your separate ways, tell him that because you want to keep the FWB relationship, tomorrow you are going to walk in and resign. Tell him that is a good thing and a sign that you want this to continue.
posted by JohnnyGunn at 12:29 AM on January 6, 2013


Answering the core question: in a casual place outside of work, invite him on a date. If he says no, that's your answer. If he says yes, tell him about your FWB dream.
posted by zippy at 1:04 AM on January 6, 2013


I think you have a crush on him. Choose which you want: a *possible* sexual relationship with a guy who has made it clear he Does Not Want A Commitment, or your actual job. 90% chance you cannot have both.

If you really want to seduce him, how hard would it be to find a new job? And, for him to find a new job? If he has a sexual relationship with you, he will be jeopardizing his job, as well.
posted by theora55 at 10:58 AM on January 6, 2013


You really can never assume that even if things don't work out they won't go horribly wrong. A friend of mine had a FWB situation with a senior coworker and despite best intentions it went horribly wrong. If you're ok with things going horribly wrong go for it.
posted by Green With You at 11:55 AM on January 6, 2013


I greatly prefer relationship sex to one night stands. So I've become friends with a guy to whom I'm really attracted. He is not "relationship material". He describes himself as a "confirmed bachelor"

So you prefer relationships, and he is a confirmed bachelor...

He doesn't want kids and I do. He can't leave the area, and I have to.

...who appears to be generally incompatible with you...

Oh, and he's my boss.

...and with whom you have a professional relationship...

He gets to bone a younger woman with big tits who doesn't want to commit to him -- what's not for him to love about this situation?

...that you are now looking to sexually objectify...

He's an alcoholic

...with a man with a history of substance abuse...

I'd hate to mess this up, because like I said, I *really* need to get laid.

...right.

So you need to get laid, and work at a job where your boss is a former alcoholic who has never had a serious relationship (from your (admittedly biased) viewpoint). He avoids you in public, but enjoys the attention when people aren't looking. I wonder if he hasn't been through the wringer a time or two (as an alcoholic) and whilst he is flattered by the attention, he may well care about his professional standing more than you. Not a judgement call, but you don't care about the job and presumably he does. He may well be flattered by the attention of a younger woman – and he obviously has had impulse control issues in the past.

You may well be able to seduce him and go about your merry way, casting off the job and moving away. But he is going to have to stay there and live with it – whatever consequences result (if any).

Overall, I'm not sure what to say about getting laid, but there is a person on the other end of the equation. A person for whom impulse control has been a problem in the past and has trouble with relationships.

This sounds like a really bad idea to me.
posted by nickrussell at 2:07 PM on January 6, 2013 [3 favorites]


"Confirmed bachelor" is not always a euphemism for gay, it really really is used by men who just don't consider themselves the type who would ever be interested in marriage and babies. Since the OP and this guy are close friends outside of work and the OP referenced the guy's previous relationships with women, it's fairly safe to assume that they're both understanding the same definition of "confirmed bachelor."

Initiating closer physical contact with someone that you really like can be "awkward" as in "this makes me nervous because it's new and we're not sure what it means yet." It doesn't necessarily mean "ew, I don't think this is working." (Consider how adolescently-awkward first kisses can be even among sexually experienced grown-ups until they find a stride...whoops bumped teeth, having to negotiate angles and kissing styles, etc.)

Anonymous, just kiss him, plus have a simple sentence or two in your head to calmly and simply get across your thesis, so to speak: You really like him as a friend + You're really attracted to him + You're a confirmed bachelorette at the moment = Why not give this a try and see if we like it?

BUT, some logistical questions to think about -- things that you two would need to agree upon and decide if this is worth it.

* Would your FWB situation actually be a secret that needs to be kept at work, or just something kept discreet, or what? How will both of you feel if people put two and two together and figure out that something's going on? Then what happens, do you deny it, is there drama, etc.?

*Even though you said that it wasn't an employment situation per se, he might feel that it's close enough to be too weird for him. But if you quit to avoid this conflict, it raises the stakes for the relationship (you quit for him) AND denies you both the enjoyment of working together and that regularly-scheduled interaction.

* Do you expect that you'll spend a lot more time with him if you're sleeping together, or do you just envision adding this to your existing level of friendship-time spent together? It's cool if you both date other people, right? Is it still okay for you both to talk about other people that you're dating with each other? How else will sleeping together change the dynamics of your existing friendship?
posted by desuetude at 2:26 PM on January 6, 2013


As a black woman who has dated white men, I find that they are usually clueless and hesitant to approach me. I have to be really obvious about my attraction to get any play.

In this case though, you can add my voice to the chorus urging you to forget about this one. It has the potential to be waaay too complicated for the fun and done you're looking for.

Try Craig's List or OKCupid. You can say exactly the kind of set up you are looking for.

If you would rather have sex with someone you know, you can ask any of your close lady friends if they know any single dudes who are available. You and your lady friends can even arrange group outings to get to know potentials before you approach them.

My last piece of advice: Dating and having sex are supposed to fun! If you get too hung up just having sex based off some arbitrary time table you won't enjoy anything and make less than ideal choices. (For example, it sounds a bit like you picked this dude in large part because he happens to be around and not so much because of chemistry.) You should think about having fun (and sex is fun) not just getting laid. Use the internet or your friends to find men that you have fun with and sex will follow. Good Luck!
posted by Misty_Knightmare at 4:35 PM on January 6, 2013 [2 favorites]


3 years is not that long.
posted by cupcake1337 at 7:51 PM on January 6, 2013


He would never do this...>>

Yes he would. See the story about the dental hygienist who just got fired after 10 years (and it was legally UPHELD) by the dentist boss SHE'D NEVER BEEN INVOLVED WITH for being "too attractive". If it doesn't suit their purposes, your well-being won't be considered.
posted by FlyByDay at 9:16 PM on January 6, 2013


There's a lot here...

white guy, black girl thing: don't worry about it. He may be intimidated by the idea of dating a black girl, so you may have to make it easy for him.

"co-worker" thing: It can be done...

alternatives to drinking: if you are both interested, it doesn't take drinking to get to the first kiss. For me it seems to take spending a few hours together and suddenly finding yourself secluded in the right place with the right feelings. What if you spent a day together and built u to it over the course of the day. A hug in the beginning, a hand squeeze later, an arm rub somewhere in there, a peck on the cheek...
posted by jander03 at 11:50 PM on January 6, 2013


Confirmed Bachelor means gay as fuck, and still in the closet officially.

Dude, George Clooney has called himself "a confirmed bachelor" as well. You telling me all the women he's dated have been beards?

That said, to the OP: in the immortal words of a web site I once frequented - make sure you're not thinking with your pussy here. I am all for hookups and flings, but there is a lot about this situation which would complicate things for you and/or him (the co-worker thing, the fact that he's more senior than you, the fact that you're going to be leaving town eventually, the fact that you haven't told us WHEN you're leaving town which means who knows if it could be a while before you do), so...I wouldn't try anything unless you've really, really thought about what the actual fallout could be for both of you, and then really, really talked with him about what the fallout could be for both of you as well.

But forcing his hand before any of this contemplation has taken place - that way lies great risk.
posted by EmpressCallipygos at 12:35 PM on January 16, 2013


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