Dating your boss' child?
May 1, 2005 3:48 PM   Subscribe

Dilemma: My boss’ daughter is pretty hot…

I work for a small firm, about two dozen employees total. Owned by a husband and wife and a third individual. About three months ago, the husband and wife introduced me to their oldest daughter, who is my age (mid-20s). She and I hit it off, and keep in touch regularly (and her parents know this). I have a fantastic relationship with the parents, both personally and professionally (the wife is my manager, and I’m frequently working with the husband, too). Now, here’s my dilemma: I’ve started to fall for their daughter. She’s really sweet, drop dead gorgeous, funny, smart, etc… [insert birds singing here]. Her mom has even, on a couple of occasions, made note of the fact that both she and I are single.

I’d love to ask her out, but I’m a bit nervous about it because of who her parents are. If I knew this girl in any other context, it wouldn’t be a question at all--I’d ask her out.

So, a two-part question:

First, do I ask her out? Do I approach her folks first to test the water with them? (And how the hell do you start that conversation??) Or do I ask her out, see how it goes, and then let them know?

Secondly, if I do ask her out, what ground rules should be set between her and I, and her parents and I?

Has anyone gone through this? Any advice is dearly appreciated!
posted by anonymous to Work & Money (48 answers total)
If you get involved, and it doesn't work out, then your life is suddenly going to be a lot more complicated than it currently is. Unless you seriously think that a) your job could easily stand a bad breakup with your boss' daughter, and b) there is a very, very strong possibility of marriage resulting from this, he smart thing to do is nothing. There are a lot of attractive girls out there who are not related to the people you work for.
posted by bingo at 3:48 PM on May 1, 2005

ask her out. life is a lot more important than work.
posted by andrew cooke at 3:52 PM on May 1, 2005

It sounds like the parents would like for you to ask her out. They know you already, and seem to like you. Know you got a good job, and maybe might one day be someone that could run the family business... Don't get ahead of yourself here though.

I'd tell the mom, your manager, that you're planning on asking her daughter out in the next 48 hours. Don't ask her permission, you are telling her what you are planning on doing as you don't want to do this behind her back. Don't make this about "getting permission" as 1) it doesn't sound like you want/need to do that, 2) in these modern times, some ladies might find it offensive, and 3) you aren't asking anyway. Tell her, that you really like her daughter and think you two could hit it off. Don't mention anything about possible consequences of a breakup and your relationship at the job. Don't mention anything like that. You don't care what the consequences are 'cause you are not going to break up with the girl. At least convey that authority and positivity. You're not looking to make sure they'll be ok with you once you screw their daughter and then want to leave her (what's the saying, "having the cake and eating it too?") You are not planning on needing to worry about that at all. If they think you are trying to cover your ass in case it doesn't work out, they will probably be unhappy with how you are approaching this relationship.
posted by pwb503 at 4:00 PM on May 1, 2005

Ask her out! If she says yes that would be the time to decide between the two of you how and when to tell her folks. Treat all parties with respect and I don't see why there should be any problem or need for any particular "rules". I hope it works out for you both.
posted by teleskiving at 4:12 PM on May 1, 2005

However you approach it, treat her with the utmost respect at all times. That way, however things go, the parents will at least feel that you acted honourably.

Sure, I'd say mention that you are planning to ask their daughter to do X (see a movie, go bowling whatever) with you. You dont have to call it a date. They'll understand.

If you are really interested in this girl, go for it. Romantic regrets are worse than almost any other kind.
posted by vacapinta at 4:13 PM on May 1, 2005

I think you should ask her out, asking her (the girl) if she thinks her parents will be cool with it. Quite possibly, they've been saying stuff like "You and anonymous would really hit it off!" all along.
posted by josh at 4:17 PM on May 1, 2005

Ask her out for one date without telling her parents. During the date express your worries in a humorous way. Since you already keep in touch with her, it shouldn't be too awkward to bring up this dilemma. Use her to test the water with her parents. If they express disapproval to her, then you wil have to weigh the consequences of going forward or backing away.
Or, if you feel comfortable enough with her already, bring it up as part of asking her out.

I've actually been in this situation, except it was the sister of one of my managers. The above is basically what I did and everything worked out fine (my work situation, not the relationship).

On preview, like josh said.
posted by Falconetti at 4:23 PM on May 1, 2005

I think the main issue here is that you might be expected to take this more seriously, more quickly than you would otherwise. That's the part you have to decide about. If you didn't know her parents, would vague thoughts of possible marriage be on your mind, or do you generally have a 'hook up, have fun' kinda attitude toward relationships at this stage?

If you're taking this seriously, I say definitely go for it. It may not work out, but that's alright; all intentions were good, etc. But, if the mention of that level of commitment is making you think, whoa, whoa, folks, I just said a date, let's not get carried away... then I think you should be a little more careful, as the parents may interpret a casual attitude toward relationships in general as a sign of disrespect toward their daughter in particular.
posted by mdn at 4:43 PM on May 1, 2005 [1 favorite]

Do it. As long as you're not a dick later on, you've can have a clear conscience if you break up.
posted by trbrts at 4:53 PM on May 1, 2005

I love my boss
His name is Ross
My boss is my (father-in-law)
posted by fixedgear at 5:07 PM on May 1, 2005

What teleskiving and josh said. My sister is quite in demand among my dad's subordinates, and she knows how to manipulate him rather well. Chances are, if she wants to go out with you or thinks it'll be possible, she'll say yes -- and then SHE'LL handle things on her parents end.

Keep the consequences in mind, though. How do you do in relationships when you're nervous?
posted by SpecialK at 5:10 PM on May 1, 2005

I second the "ask her out" advice and I strongly second the advice NOT to talk to her parents about it first. She's an adult and so are you, and you and she can discuss how to deal with her parents and ground rules and all the rest of it if and when the time comes. Life is more important than work, but you should be prepared to keep the two as separate as you can, even if you and she date.
posted by biscotti at 5:38 PM on May 1, 2005

Don't ask her out with the intention of having a brief fling. If you're marriage-minded, on the other hand, go for it.
posted by ikkyu2 at 6:20 PM on May 1, 2005 [1 favorite]

What are you, crazy? You're setting yourself up for not one relationship, but three, so you can't fail to p@#$ off somebody at some point when they find out you're not the person they thought you were.

Let me preempt the question you're going to be posting here in about 6 months time - you shouldn't have done it in the first place....
posted by forallmankind at 6:43 PM on May 1, 2005

Go for it. But be prepared to be on your best behaviour. If you screw this one up you're royally screwing yourself.

The only other thing I can say is that it'll be a pain to have her parents so involved right from the start. You'll be on a marriage track from day 1. That's not always best. In this day and age in western cultures the parents mostly hang back. These folks will be right in your face signing your paychecks, eyeing you to make sure you're treating their daughter well. You damn well better return her phone calls, remember her birthday, tend to her orgasms, etc or you'll be pissing off not only your gf but your boss.

I can imagine you getting into such a relationship, and 6 months in feeling completely ensconced by the sense of family, being welcomed into the fold but these kind folks and their luscious daughter - it could be really sweet. But on the other hand if you ever foul it up you'll be kissing your entire life goodbye, not just your relationship.

Think about it carefully. They seem to trust you. Are you up to it? Are you worth it? I say go for it but recognize that what you're going for is the brass ring, the whole enchilada, there'll be no in-and-out with this one. The way your question is framed on the homepage I wonder if you recognize that. Heh. Typical mid-20s ;)
posted by scarabic at 7:03 PM on May 1, 2005

You're going to need to trust her a lot more than a random GF. If she wants to play you, she can make your life a living hell.

Do you trust her?
posted by krisjohn at 8:24 PM on May 1, 2005

It really depends on the parents. If they're cool, they'll be cool. If they are secretly weird, you are about to find that out. Unless they are totally square, I can't imagine the fallout from things not working out with their daughter to interfere too much with work. The big risk here is crossing over from professional relationship to a quasi-familial one.

And I'd quadruple-condom if I were you.
posted by _sirmissalot_ at 8:32 PM on May 1, 2005

Could you ask her to accompany you to some charitable or environmental event, or help you with some activity that isn't seen as a "date"?
Ease in to the relationship.
posted by weapons-grade pandemonium at 8:38 PM on May 1, 2005

Simple. Quit your job, then ask her out. If it works out, the parents will hire you back, since you obviously weren't using the daughter to advance your career. If it doesn't work out, you wouldn't want to be working there anymore anyway.
posted by davelog at 9:17 PM on May 1, 2005

Keep the job. Ask her out. Do what you would normally do if she were not related to anyone you know. If things don't work out, either deal with it or leave.

Is the job so great that you have to ask this question?
posted by bh at 9:50 PM on May 1, 2005

I disagree with the posters who assert that automatically, the parents will be pushing you on the marriage track. Unless the parents come from a culture of arranged marriage, this seems overly paranoid to me.
In the other direction -- quitting your job with the idea of instantly getting it back does sound romantic, and also, really dumb. I sure wouldn't want an employee given to such crazy gestures.

What's the worst that can happen? You date her for a while, you do something stupid and break her heart, her parents blame you and don't want you around any more, and you get another job. If this job is so great and/or it would be so difficult for you to get another, then perhaps this is a risk you may not want to take. Otherwise go for it.

On preview: bh's question.
posted by Aknaton at 9:52 PM on May 1, 2005

Just go for it. Don't ask the parents, don't be a jerk, don't let it affect your work, and _don't_ miss what sounds like a great opportunity. She may or may not be "the one", but it'd be a shame to pass up a chance like this.
posted by LairBob at 10:36 PM on May 1, 2005

You might regret asking her out, but you will definitely regret not doing it.

Let us know how it goes!
posted by LarryC at 12:17 AM on May 2, 2005

Some good advice here, but do consider the comment from krisjohn.
posted by Goofyy at 12:19 AM on May 2, 2005

Mixed thoughts here, but I will definitely say that if you decide to ask her out, don't do anything like "asking the parents' permission" first. It attaches way too much importance to the date, which would be really awkward if the initial attraction doesn't play out.

On the other hand, since you basically see her parents every day, it would also be weird to be totally silent about it, so you might say something like, "oh, hey - it looks like Mary and I are going to see blah-blah show/movie Friday.

It's really difficult to find a job you like where you have a fantastic relationship with your employers, so obviously one doesn't want to jeopardize that. But it's also really difficult to find that one wonderful person who could be the love of your life, so it seems kind of crazy to just let that possibility slip away, unexplored.

From a social/psychological aspect, I would say it is probably promising that you like her parents so much — after all, they raised her, so she is at least partly product of all those qualities you appreciate in your employers. So that's auspicious. But ultimately, if you decide to pursue the girl, you will be left with no choice but to trust to the fairness and objectivity of her and her parents in the event that things take a bad turn between you. You won't really be able to control that by extracting agreements or setting guidelines beforehand, so it's definitely a risk.
posted by taz at 12:23 AM on May 2, 2005

Gor for it. Don't forget the parents, but they can find out sometime after the first date -- I agree with others above in that the daughter will know what's best in that regard. And what's wrong with a fling anyway? That may be her desire as well. Casual is often the norm. Everyone knows it. It's for the 2 individuals to decide. Be suitably professional/impressive at work and you'll shore up the job - who knows about psychological workplace weirdnesses down the track. They can become the subject of another AskMe Q, if needed.
posted by peacay at 12:31 AM on May 2, 2005

If you care about the job, don't do it.
posted by grouse at 3:12 AM on May 2, 2005

I disagree with the posters who assert that automatically, the parents will be pushing you on the marriage track. Unless the parents come from a culture of arranged marriage, this seems overly paranoid to me.

And what's wrong with a fling anyway? That may be her desire as well. Casual is often the norm. Everyone knows it.

I don't think it's paranoid to suggest that parents may think in somewhat more long-term terms than 20-something kids. In my 20's, I would absolutely have been in the "whoa, whoa" category myself. The thought of marriage used to give me hives, and I never worried about I wanted out of a relationship beyond "are we enjoying this?". But my mother still asks me about various people I did not marry, and now that I'm in my early 30s, I actually understand the attitude she had, which was generally a concern with whether the relationship was 'going anywhere.' I think as you get older, you (well, a lot of people, anyway) realize that life's actually pretty short, and that it'd be nice to have a sort of 'life story' that holds together (rather than a bunch of random, unconnected paragraphs).

Sure, it depends on the particular parents, but I would bet that a good portion of married people over a certain age actually will be thinking of marriage pretty early on. I mean, at this stage in my life, it occurs to me pretty much right away to distinguish between "potential mate" and "just for fun" (I'm not saying the categorization is definite to my mind or anything, but just pointing out that it honestly does not seem weird anymore for the question to occur to me), and I'm only 31 and not even sure if I want to get married! These parents are at least in their mid-40s and have been happily married for somewhere around half their life, so they may very well think it's pretty central to their daughter's life.
posted by mdn at 5:44 AM on May 2, 2005 [1 favorite]

Go for it. Tolerable jobs are easier to find than great relationships. As long as the parents are cool and you're not a dick things should be fine no matter how the relationship ends up. If you do eventually break up with her just have a talk with the parents, explain it didn't work out and you hope there is no hard feelings, etc. If they fire you or make your job a living hell then find a new job and perhaps seek legal action, but all that's jumping too far ahead.

One thing nobody has mentioned, when you're dating your boss's daughter you should be prepared for your coworkers to automatically see favoritism around the office. Even if there is none, they'll say there is. If your office has a better view, if you get a promotion, or if you get a shiny new red Swingline stapler, as far as your coworkers are concerned it's only because you and the boss's daughter are making the monster with two backs.

Coworkers will do that no matter what though, so ignore it or play into their jokes.
posted by bondcliff at 6:00 AM on May 2, 2005

If your question was phrased more like, "The boss's daughter is hot... I'm thinking about banging her as soon as she gets her braces off..." I would suggest you perhaps reconsider. However, what with your birds singing and all that, it seems you might have something more real here, so I say go for it. The fact is, no matter how good your job is, jobs really don't tend to last all that long these days anyway. Eventually the job is likely to end for one reason or another, and if you never made your move, you'd end up regretting it big time.
posted by spilon at 7:31 AM on May 2, 2005

There are loads of smart, funny and gorgeous women out there but a good, warm working environment filled with people you respect and admire is extremely rare. And the power relationships involved seem particularly devious. I can't imagine having a girl friend who'd have the direct line to my boss. You'd be better off asking her to put in the good word among her friends.
posted by nixerman at 7:48 AM on May 2, 2005

Do it. Ask her out. She'll tell her parents. From what you've told us, it's what her parents had in mind.
posted by blasdelf at 7:56 AM on May 2, 2005

Oh, and if you do the deed and ask her out, show her this thread.

Remember: "There are no save points when it comes to ladies, honey.
posted by blasdelf at 8:01 AM on May 2, 2005

Tolerable jobs are easier to find than great relationships.

Yeah, but great jobs are, equally, harder to find than tolerable relationships. Neither one is really a meaningful factor in this decision. There is no dilemma: This would be a huge mistake. There is already an unwritten workplace rule against dating your co-workers and it's not difficult to see that it would also apply to, say, the boss's daughter for similar reasons. The decision, in other words, has already been made for you; you are now deciding whether to break that rule or not. I guess if you're a rulebreaker, you will, and if you're not, you won't.
posted by kindall at 8:44 AM on May 2, 2005 [1 favorite]

Also bear in mind that, at this point, it's possible that blowing her off will create some bad feeling, too. I'm not sure how far along things are.

When I said "marriage track" I didn't mean that the parents would push for a proposal right away. The marriage track is long and begins with simple things like dating. But a set of parents who already know and like you, who set you up with their daughter, are not doing it for the sake of your happy penis pleasure. They may be fine with you two dating. They may be fine with you two fucking. But they're likely thinking long-term, and anyway will hold you to a high standard of "honor" no matter what form the relationship takes.
posted by scarabic at 9:05 AM on May 2, 2005 [1 favorite]

there may be an unwritten rule against dating co-workers and your boss' daughter, but it's violated all the time by people ... sometimes with bad consequences, sometimes with wonderful ones

your personal life and your work life are going to be indistinguishable if you take her out and things start clicking ... make sure you'll be ok with that before you start

the real question i think isn't necessarily "what if we go out for awhile and decide to break up?" ... it's "what if we're together and i get a better job offer?"

one thing you're going to need to face down the road is how she feels about the family business ... did you plan to work there a long time? ... if you're with her is she going to pressure you to stay? ... it's early, of course, to deal with these questions right now, but they will come up at some time

in short, the real danger of a serious relationship with her isn't just that you'd lose your job if you broke up ... but that you'd keep your job when you shouldn't if you stay together

ask her out, but realize what you could be getting into
posted by pyramid termite at 9:23 AM on May 2, 2005

If her parents are at all cool (and it sounds like they might be), they'll appreciate your situation, if you do decide to do it.
Heck, maybe you could even double date with them, but ease into that.
I kid of course.

Also, is there a possibility of her coming to work at your job? That could make things more confusing8...

Oh, and if you do it be sure to keep your weeks open for emergency AskMe questions...
posted by hellbient at 9:24 AM on May 2, 2005

I'm interested to see the leftish leaning MeFi gallery expressing somewhat conservative ideation about a fundamentally enjoyable exercise such as dating somone who's considered hot by the poster.
It's of course prudent to take into account the unusualness of the workplace connections but extended philosophizing over such factual asides may be a telling regret in the future should the impulse be stifled now. Too much thinking can itself be a barrier to finding a compatible partner. I just think it's a little early on, before the first date, to give serious consideration to the marriageability factor. That's only going to come with exploration of the relationship and that's only going to come by having a first date and seeing what happens.
Les affaires d'amore are more fulfillingly realized when the heart rather than the head takes the lead, at least in the beginning, IMHO.
posted by peacay at 11:21 AM on May 2, 2005

If you're falling for her, you should ask her out. Your feelings are likely to continue to grow, and it'll be very painful if you never take that chance and see whether it could go further.

I agree with whoever said that her mother (your manager) was hinting that she'd approve -- she wouldn't point out that you're both single if she didn't want you dating her dauther.
posted by me3dia at 3:15 PM on May 2, 2005

You can do it!!!
posted by jackofsaxons at 4:34 PM on May 2, 2005

Les affaires d'amore are more fulfillingly realized when the heart rather than the head takes the lead

Actually, letting your heart do the thinking is a bad, bad idea that nearly only leads to suffering. If you haven't learned that yet, this could be a singularly messy way to do so. So, if you want a life lesson, go right ahead.

Your feelings are likely to continue to grow

Only if you let them. Who's in charge of your life, you or your feelings? Make decisions with your brain.
posted by kindall at 5:46 PM on May 2, 2005

I can't believe how many people here are placing more importance on a damned job than a possible love. I wonder if those people fear unsuccessful job hunt, or if they simply find it trivial to meet exceptionally fantastic women.

And it sounds like they'd be happy to see you dating their daughter. Mothers don't go around saying 'you and my daughter are both single' unless they have something in mind.
posted by mosch at 6:50 PM on May 2, 2005

whoa kindall you cold hard cynic you
posted by peacay at 10:54 AM on May 3, 2005

Oh, well. Kindall has a point. I'm little Miss Logic, but I've chosen with my heart twice (and my brain, never). Once turned terribly painful, and once was the best thing that ever happened to me (15 years now!). If I had only experienced the first, I would be completely agreeing.
posted by taz at 1:59 AM on May 4, 2005

so you're saying your 50% happy with the 15 years then?
posted by peacay at 9:27 PM on May 4, 2005

This thread is worthless without pictures.
posted by thedevildancedlightly at 4:19 PM on May 17, 2005

I think they made a number of movies on this topic, they are all quite hilarious. Rent them and see what happens...
posted by raster at 1:31 PM on May 25, 2005

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