What’s Wrong With You: Sexy Boss and Jewish Mother-in-Law

Dear Judith,

I’m an actress who works as a legal assistant to pay the bills, and I’m completely obsessed with my boss.  He’s incredibly hot (IMO), successful, a teensy bit shy, and really just a nice, all-around decent guy.  He’s also Jewish, which is important to me and also seems like some kind of sign because I haven’t been attracted to anyone Jewish in a long time. 

But.  But.  He’s my superior, which means that no matter how much I flirt with him, he’ll never do anything about it.  So how aggressive can I be?  Sometimes when we’re working late I want to shut the door to his office and take off my clothes.  Suggesting coffee didn’t work.  

I’m not worried about losing my job because he wouldn’t do that to me, and I’m not worried about things becoming awkward between us because we’re friendly enough that it would pass.  I’m not even worried about rejection because what do I have to lose?  I have to hook up with him at least once before I die.  And I could get hit by a car tomorrow.  

Yours truly, 

Pining Paralegal

Dear Pining,

Shutting the door and tossing your bra onto the bookshelf might work on TV, but in real life you should have a solid history with someone–romantic history, not work history–before you try to nail him on his desk.

Where does your fantasy go after this one shag upon which your happiness depends?  I’m not going to spell out all the bad places it could roam.  Review the men from your past–the jerk who dumped you for your college roommate, the one who “borrowed” your car while you were away at your cousin’s wedding–these are just examples to get you started.  Of all the men you’ve dated/pursued/rejected/defriended, do you want your paycheck hanging on any of them?

The less that transpires between you and your boss now, the less you’ll have to regret after you realize he’s not who you thought he was and come to despise him.

Speaking from experience,



Dear Judith,

I’ve been dating a guy for almost three years and we’re thinking of getting engaged.  My problem is his mother.  Rather, his relationship with his mother. 

They talk on the phone fifteen times a day, and he always wants to include her in whatever we’re doing.  I feel like I can deal with it because he listens when I put my foot down (like on Valentine’s Day and my birthday), but my friends are making me scared that if we get married, she’ll feel like she’s losing him and get worse.  Is that seriously possible?  

Thank you, 

Cautious Miss

Dear Cautious,

Your boyfriend reminds me of the husband of one my friends.  According to him, a guy who treats his mother well will treat his wife well, too.  According to her, he interrupts whatever he’s doing when his mother calls (except for sex, at least), and when his mother visits he picks fights with my friend and treats her like a servant.  Does that sound like wedded bliss?

For the record, there are worse things in life than a stereotypical Jewish mother-in-law.  If you were trying to put your kids to bed but your husband wanted to watch cartoons with them, you wouldn’t mind her happening to call and distract him.  And if you and she were on the same side about something you could count on him falling in line.

No need to parse the finer points at this stage, though.  You say you’re thinking of getting engaged — have you looked at rings?  Discussed a date?  Let me know when your boyfriend cuts his cord and actually proposes.

Wishing you well,


What do you think?

About The Author

Judith Basya

Judith Basya is Heeb's Literary Editor. She writes an advice column (and an advice blog: www.asktinymom.com) so her psychology degree doesn't go to waste. If your problem can be solved in <140 characters, she's on Twitter. If it's complicated, please email Judith @ Heebmagazine.com.

2 Responses

  1. Danny

    Pining Paralegal,

    Why not try the advice often given to men. Get to his balls through his brain and heart. He sounds like someone who has his zipper under control. Share ideas, feelings and interests and give him space to share his own. There is the old saw that Jewish guy’s idea of foreplay is 30 minutes of talking about himself. He may not be a narcissist so you may to just figure out how to share mutally. Perhaps the fabulous boff is never meant to happen. But if it is, this way you may get much more than 1 night.

  2. Lance

    I thought Jewish foreplay was 2 hours of begging.
    Anyway, some things just don’t mix. As Seinfeld says, when “worlds collide,” bad things happen.
    Not to be crass, but there’s an old earthy saying that one does not “shit where one eats.”
    If you’re so confident you can get another job, consider telling him how you feel and offer to resign if that is what it would take to make it possible. Or, if he says the attraction isn’t mutual, keep your day job and focus on someone else.


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