The Naked Advice

Model & Writer Liz LaPoint answers your questions about dating, sex, and relationships

Chuck wrote: “First off, I’m shy and I have a hard time meeting women (people in general). Think “Raj” on ‘The Big Bang Theory’. I have a feeling about what that is due to, but it’s major and not really the point of this. (Yes, I’m trying to work on it, but…it’s a bit of a catch 22.)

As for my ‘issue’, this is a bit weird. The boss’s daughter. There have been a few times when I’ve caught her looking at me out of the corner of her eye. Another time, she turned the corner, looked at me like a deer in headlights and then turned the corner after ducking her head.

That’s not the ‘worst’ of it though.

A computer chair she was in had a squeaky back rest. She asked for some WD-40, which I got for her. She gets on her knees, shakes the can… and then gives me a ‘look’. Yeah, that one. I was just leaning in the doorway, and I noticed she got some WD-40 on her hands… So I got her a paper towel… Yeah, I ‘realized’ that later…

She has since gotten another position with another company, and I had also learned that she (most likely) has a b/f.


In my opinion, her actions were slightly more than just ‘friendly’.

She’s 10 years my junior, and more educated than me. (I don’t even have an associate’s, she’s a lawyer.) Not to say I’m not intelligent, just that school doesn’t work for me. (Catch 22 again.)

So basically, what the fuck? Do you think there was anything there? Or was she just playing her position?”

Liz says: Wouldn’t the world suck infinitely less if people were clear in their motivations and intentions? There are few things worse than trying to decode and decipher someone’s behavior toward us, especially in the romance department.

Everything you described sounds to me like a chick who might have picked up on your attraction to her and milked it for an ego boost. There are people who flirt only with those they are actually interested in and then there are people who flirt to get attention or manipulate.

I suppose there’s a chance I’ve got her all wrong, but she seems to fall into the latter category. Here’s why:

1) She “most likely” has a boyfriend.

2) Your descriptions of eye contact and flirtations, which may have been unintentional, are too unclear (hence your letter, I know, but stay with me) and usually when two coworkers are really attracted to each other, it gets pretty obvious at some point. They begin finding excuses to talk to each other more, they try to get info on each other from other coworkers, and eventually the attraction is too difficult to continue putting off so someone acts. The act could be a request for a date, a kiss in the empty office, a note left behind on your desk. The point is, if she was into you too, I doubt you both would’ve let it go the way it did.

I say forget about her and be thankful nothing happened between you two, since her being the boss’s daughter just sounds like drama no one needs.

Since you mentioned you tend to be shy, the next time you’re attracted to someone (who isn’t related to the higher-ups) ask her out on a real date as soon as you can, that way you’re not driving yourself crazy trying to interpret everything she says and does. If she says yes, then yay! If she says no, then you can leave her alone and nurse your wounded ego without wasting so much time wondering if she is interested. It’s a win-win!

Good luck, Chuck!


2 thoughts on “Was The Boss’s Daughter Attracted To Him?

  1. Great advice as usual Liz! I love the outlook that getting a no is still a win. More guys need to see rejection that way.

    Liked by 1 person

    1. Yes! Thanks Demetrius đŸ˜‰

      Liked by 1 person

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