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Dating Your Boss

post #1 of 121
10/25/07 at 4:40pm
Thread Starter 
I'm thinking of taking a big leap here, and I don't know if, to quote Mr. Tim Olymphant, the juice is worth the squeeze.

I've worked at a daycare center since summer, and I have been lusting over my boss. I'm only 23, and I can only assume she's in her late thirties. She's really funny and attractive, and stays in really great shape. I'm the only unmarried guy working there, so I've always stuck out as far as my co-workers, so she has a different dynamic with me. I used to think we were being playful, but lately, I've been thinking it's an attempt to be flirty. The signs are obscure and elaborate, so maybe I'm mistaking them, but it doesn't seem like a stretch- the first thing I did when I met her was check for a ring, and the fact that she doesn't have one feels like a foothold I can get into.

There are so many foibles attached to the idea of dating or at least sleeping with my boss that I feel like I shouldn't do it, but lately, those are the things attracting me to the idea more. It's clear she's used to dealing with kids and precocious parents all day, and someone like me, a young but mature fellow with no attachments or hangups, might represent an attractive notion for me. Plus, you know- she's my boss... the sexual fantasies and dynamics playing out in the darkest areas of my head are killing me. She is HOT.

Has anyone else here ever dated their boss?
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post #2 of 121
10/25/07 at 4:43pm
Bruce Springsteen gave me a handjob. Is that close enough?

Seriously, it sounds like if it didn't work out you could find another place to work if it got ugly. Unless it's KABONG DAYCARE and you're tied to it by name.
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post #3 of 121
10/25/07 at 4:45pm
When she's fellating you, no matter how good an idea it sounds at the time, don't agree to whatever she asks you that isn't sex related.
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post #4 of 121
10/25/07 at 4:49pm
Quote:
Originally Posted by Nick Nunziata
Bruce Springsteen gave me a handjob.
You got a little bit of that human touch?
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post #5 of 121
10/25/07 at 4:50pm
Find out if she's married for sure, dude.
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post #6 of 121
10/25/07 at 4:50pm
Quote:
Originally Posted by KABONG
It's clear she's used to dealing with kids and precocious parents all day, and someone like me, a young but mature fellow with no attachments or hangups, might represent an attractive notion for me.
Sounds as if your are talking yourself into masturbation. Get yourself drunk first, be sure to tell you that you love you, and then pound yourself with yourself while thinking of you. In front of a mirror.
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post #7 of 121
10/25/07 at 4:51pm
I don't see it ending well at all. I have an issue with dating anyone I work with period, which is killing me because I am absolutely drooling over a girl in my office. If something happens, especially with a boss, how do you keep working there?

But if you can get a few great rides out of it, and leaving the job won't kill you, go for it.
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post #8 of 121
10/25/07 at 4:55pm
This sounds like a recipe for total disaster. She's 15 years (maybe) older than you, you work for her, and you have no idea if she's married? And you're basing your decision to go for it on the vague sense that maybe she's flirting with you? No no no no no no no no no no....

edit - You must spread some Reputation around before giving it to the irrepressible Kevin Matchstick again.
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post #9 of 121
10/25/07 at 4:55pm
Been there, done that, does not work.
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post #10 of 121
10/25/07 at 4:56pm
I won't end well, no matter in which orifice you go in. Abort.
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post #11 of 121
10/25/07 at 4:59pm
Chiming in with the women-folk (and odd-men out Billy G and Martin Savage) here. Bad idea, just never ever go for it with a co-worker, especially a boss. Just a whopping no no no.
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post #12 of 121
10/25/07 at 4:59pm
Is it dating or hooking up? Because it sounds more like hooking up buddy. Way to go!
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post #13 of 121
10/25/07 at 4:59pm
Quote:
Originally Posted by Martin Savage
I won't end well, no matter in which orifice you go in. Abort.
This disturbs me on many levels. I hope that's a typo.
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post #14 of 121
10/25/07 at 4:59pm
I don't see how you factor into the equation, Martin. But, it sounds dirty regardless.
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post #15 of 121
10/25/07 at 5:00pm
Line up another job, then go for it. If you get some action, quit. If you don't, quit.
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post #16 of 121
10/25/07 at 5:03pm
For Halloween dress up with the dick in the box costume and put her name on the present.

Also, have another job lined up.
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post #17 of 121
10/25/07 at 5:03pm
Quote:
Originally Posted by The LD
I don't see how you factor into the equation, Martin. But, it sounds dirty regardless.
It's just that no matter what happen, from a sexual encounter to a full relationship, and no matter how attractive or promising it looks, hooking up with your boss will invariably always end up badly. You risk more than emotions here.

Hey, you can try it, but update your resume first.

EDIT: Joe beated me to it.
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post #18 of 121
10/25/07 at 5:06pm
I like the fact that this could all go down in a daycare center. Ask her out for juice boxes one night.
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post #19 of 121
10/25/07 at 5:07pm
That's it, KABONG. I'm pulling my kid out of there.
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post #20 of 121
10/25/07 at 5:11pm
Although the idea of a KABONG DAYCARE could make for an interesting movie. It's either comedy, horror, or porn. Or the 3 together.
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post #21 of 121
10/25/07 at 5:11pm
WAIT!

She probably has unreal babywipe techniques...
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post #22 of 121
10/25/07 at 5:12pm
Thread Starter 
I meant to imply that the first thing I did was try to find out if she's married. She isn't.

I feel like I'm wearing Bad Idea Jeans, here.
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post #23 of 121
10/25/07 at 5:12pm
Quote:
Originally Posted by misfit
I like the fact that this could all go down in a daycare center. Ask her out for juice boxes one night.
Aw, shit. Now I'm going to spend the next 2 hours trying to come up with the perfect "Capri-Sun punching it in the hole" joke. Thanks a lot.
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post #24 of 121
10/25/07 at 5:15pm
Kabong, if you have ANY role-playing fantasies, she MAY be the best possible candidate.

DO IT! DO IT!
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post #25 of 121
10/25/07 at 5:18pm
Well, now you might have a legitimate reason to say "The boss is really riding me!" when trying to get out of obligations like funerals, reunions, etc.
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post #26 of 121
10/25/07 at 5:19pm
You want to date an older woman. Who is your boss. At a daycare center.

Why not just fuck your mom and get it over with?
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post #27 of 121
10/25/07 at 5:19pm
I am very sorry but am I the only one slightly disturbed that a 23 year old male is working at a daycare center... that goes by the name Kabong on the internet and posts about his sexual lusts.

Being a dad and reading this is just off-putting. Dude, you need to quit your job and find another one pronto. Then go date your ex-boss.
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post #28 of 121
10/25/07 at 5:20pm
Make sure when you're bangin', you throw in a "who's YOUR boss?!?!"

But seriously, if it's a career, do not under any circumstances. If you don't mind losing or having to leave your job (which will probably happen when you don't have a long meaningful relationship with her forever ever and it ends either badly or with the detonation of an awkward bomb), go for it. Simple as that.
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post #29 of 121
10/25/07 at 5:25pm
I'm a guessin' you're naive in the ways of love. I would fish in your own pond. If she's older than you and wants a relationship or someone to fuck, she'll let you know. Being flirty with another single person who you work with is a very very very common thing. Also, you've been in lust for months, your glasses are coloured.
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post #30 of 121
10/25/07 at 5:26pm
Don't do it. One thing I haven't seen anyone else mention is the reaction from your co-workers. If you two do hook up, it will only be a matter of time before people start seeing her playing favorites with you over anything, justified or not. While I think most guys are interested in older women at some point in there lives (or most of their lives), this is not how you want to go about acting upon said interest.
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post #31 of 121
10/25/07 at 5:28pm
Quote:
Originally Posted by Soul Ahn Ice
Make sure when you're bangin', you throw in a "who's YOUR boss?!?!"
Tony Micelli?
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post #32 of 121
10/25/07 at 5:28pm
Quote:
Originally Posted by donde
donde do it.
I'm confused.
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post #33 of 121
10/25/07 at 5:37pm
Quote:
Originally Posted by donde
While I think most guys are interested in older women at some point in there lives (or most of their lives)
I was always interested in "The Golden Girls".
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post #34 of 121
10/25/07 at 5:44pm
This could work. Some soft Wiggles music, dinner by night light. Perhaps some JoJo when things really start cooking.
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post #35 of 121
10/25/07 at 5:46pm
Quote:
Originally Posted by Kevin Matchstick
I'm confused.
You must spread some Reputation around before giving it to Kevin Matchstick again.
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post #36 of 121
10/25/07 at 5:54pm
It's simple.

Show her this thread; muttering under your breath, "Damn, this could be ME. Except I'd SAY something!"

This COULD work...
Unless your name really is KABONG.
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post #37 of 121
10/25/07 at 5:56pm
Quote:
Originally Posted by Soul Ahn Ice
But seriously, if it's a career, do not under any circumstances. If you don't mind losing or having to leave your job (which will probably happen when you don't have a long meaningful relationship with her forever ever and it ends either badly or with the detonation of an awkward bomb), go for it. Simple as that.
Best advice. The chances of this working out are far from good. If the job doesn't mean that much to you - enjoy yourself, take the risk. If this is a long-term job, DON'T!

But then, many a romantic comedy has arisen from such situations. Make sure you get cast approval when you sell this story.
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post #38 of 121
10/25/07 at 6:01pm
Hey Kabong, I remember following the daycare follies with you this summer, and sharing my own. I've been at it a few years longer than you, and I've witnessed this thing happen nearly word for word. Daycares and community centers are notorious for this type of stuff.

When this eventually ends (unless you're both magically thinking long term), you're going to want to move away from there. Thanks to easy friends-gossiping-with friends, and the easy networking thats literally a button press away with phone and email systems, everyone in the town is going to know the situation, and there's no way this is going to be contained to one centre. Congrats, you've just fucked yourself out of a job, and its going to be too awkward to work, unless you have absolutely no scruples.

Also, working in daycares and centers is usually a means to an end- some other career in childcare like teaching or social work. At some point you're going to have to call this boss and ask for a reference letter or phone evaluation, and if she's no longer taking any grade-A Kabonging, that shit can get messy, yo.

Don't do it, man. Instead, take advantage of the only office perk available: suggest that they hire that incredibly nubile 18 year old applicant and quickly weasel your way into that situation.
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post #39 of 121
10/25/07 at 6:05pm
Quote:
Originally Posted by Patrick Ripoll
You got a little bit of that human touch?
That's Rick Springfield...

BTW, this thread is worthless without pictures....

As for Kabong DayCare....I want my kid to go there....although I bet they're inspected daily by the state.
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post #40 of 121
10/25/07 at 6:06pm
Quote:
Originally Posted by Dr Vivisector
That's Rick Springfield...
Oddly enough, it works for either.
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post #41 of 121
10/25/07 at 6:09pm
Quote:
Originally Posted by Soul Ahn Ice
But seriously, if it's a career, do not under any circumstances. If you don't mind losing or having to leave your job (which will probably happen when you don't have a long meaningful relationship with her forever ever and it ends either badly or with the detonation of an awkward bomb), go for it.
Actually, if this is your career, you clearly have no chance at future happiness anyway so by all means you should go for the office romance.
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post #42 of 121
10/25/07 at 6:10pm
I think you should go for it. You should definitely go for it. Lust always trumps daycare.
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post #43 of 121
10/25/07 at 6:10pm
Dating your boss is not only risky for your own job or hers, but can lead to third-party sexual harassment lawsuits against the day-care center (i.e., other employees perceive you as getting job-related benefits that they don't get). This is the very definition of "bad idea".
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post #44 of 121
10/25/07 at 6:14pm
Thread Starter 
Quote:
Originally Posted by captain_oats
Don't do it, man. Instead, take advantage of the only office perk available: suggest that they hire that incredibly nubile 18 year old applicant and quickly weasel your way into that situation.
This is doable.

But is she going to have that "older lady" mystique? That criminally equipped body? I mean christ, she's wasting her talents being stuck at a desk taking calls from concerned parents.

I'll stop. I'm sure you've all ruled out daycare for your future spawn.

For the record, it's not a career.
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post #45 of 121
10/25/07 at 6:17pm
Oh, come on. The women here are invariably going to give you bad advice because they think you're misgogneysiynsistic. I don't even know how to spell that word because it's stupid and probably made up by a woman.

Let's put it this way. You typed up a blog on an Internet message board asking anonymous people what they think you should do. Obviously you want to do it. And if you want to do it, it probably can't be all that bad, right?
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post #46 of 121
10/25/07 at 6:22pm
Quote:
Originally Posted by Diva
D (i.e., other employees perceive you as getting job-related benefits that they don't get).
A piece of the action?
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post #47 of 121
10/25/07 at 6:30pm
In my case this actually worked except it was an electronics store, not a day care, and 7 years instead of 15. I say go for it.
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post #48 of 121
10/25/07 at 6:31pm
Well, she wasn't my boss, but I quit my job and started dating a co-worker right afterwards. We got married five years later. Been married for almost two years, and I have to say it was the best decision I have ever made.

But to repeat, she wasn't my boss, she is only a little bit older than me, and from the start I was looking for something more than a quick lay.
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post #49 of 121
10/25/07 at 6:36pm
Quote:
Originally Posted by benfortenberry
In my case this actually worked except it was an electronics store, not a day care, and 7 years instead of 15. I say go for it.
I bet the post coital talk was grippingly fun. Did you wax poetic about AC vs DC and resistors?
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post #50 of 121
10/25/07 at 6:37pm
Quote:
Originally Posted by cobane
Oh, come on. The women here are invariably going to give you bad advice because they think you're misgogneysiynsistic. I don't even know how to spell that word because it's stupid and probably made up by a woman.

Let's put it this way. You typed up a blog on an Internet message board asking anonymous people what they think you should do. Obviously you want to do it. And if you want to do it, it probably can't be all that bad, right?
Listen to cobane. It's just like he said: words are hard and blabbity blabbity bloo.
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