Categorized | Dear Dr. Karen (Q&A)

Flirting Without Being Too Obvious

Posted on 11 November 2009 by Dr. Karen

Dear Dr. Karen,

Does he like me? Is he just being friendly? And has the window closed?

Okay, new guy at work. Very attractive. So all my female co-workers are all over him. However, although he’s attractive, I am not as forward as them. He turned down their advances. He started talking to me, right away. Sometimes we talk for a hours at work. He comes by cubicle all the time. Sometimes I think he’s interested because he will say things like, what type of guys you like, what are you doing this weekend…etc.

He smiles or says Hi every time we pass each other, and there are times that if I am in another vicinity of the office, he will be there 5 minutes later! It’s weird. I caught him staring at me on numerous occasions. He also used to ask me for the lunch menu at our local diner, than I found out he never even visited that place! Also, other co-workers that did not talk to me, talk to me now, I believe because of him and our ”friendship”.

He hasn’t asked me for my number. Also, I don’t pick up on cues, (because I’ve been told that he has dropped subtle hints) so, I’m thinking he may think I’m not interested anymore, and sometimes, I think maybe he’s just being friendly. How do I step it up without being overt. Ooh…he is the new guy, and due to everyone fawning on him, he has been staying low-key…which makes me nervous talking to him.

What should I make of this?


Dear Sijay,

The first thought that came to my mind when I read your letter was, “What a delightfully fun position to be in!”

Sijay, if you’re getting feedback from others (whom you trust) that the New Guy is dropping hints, then he is either interested in you or he is playing a game where he wants you to be interested in him because he is used to all the attention and can’t seem to get yours!

So Sijay, it feels as if you could use lessons in creative flirting. Flirting has been given a “bad name” over the years, but actually, what it entails is energetic play. It is like a dance. There is inappropriate flirting – “coming onto” someone sexually just to manipulate them and get attention. However, there is safe and fun flirting that is connecting and enjoyable without being manipulative.

Since your style is not to be too forward (which probably got his attention in the first place), my suggestion to you is the engage in “flirting” by asking questions and stating your observations. Start with neutral questions and observations.

Here are a few suggestions you can play around with in your mind to see if they resonate with you:

While you’re in conversation with the New Guy, you might suddenly say:

YOU: You know what, New Guy? I’ve made an interesting observation.

HIM: Really? What?

YOU: I’ve noticed that ever since you came to work in this office, all the women here have been clamoring over you. What’s that been like for you? So what’s it like getting all this attention?

HIM: (blushing) ah, er, really? Or he might say,

HIM: Nah, I’m not interested in them.

YOU: Yes, really. Haven’t you noticed? Or

YOU: So you’re not interested in them? Really? So is there someone special in your life you’re not telling us about? Or

YOU: Gee, I was wondering about what kind of person you would be interested in?

YOU: Hmmm, you’re not playing “hard to get” are you?

Next time he asks you questions like

HIM: What are you doing this weekend?

You might wish to get up the courage to answer,

YOU: Why, are you going to ask me out?

or maybe you could be more creative and say,

YOU: Well, I’d absolutely LOVE to see the new movie, X, this weekend, but I don’t really feel like going alone….so
what are you up to?

Then you can see if he takes the hint. If he’s been hinting to you and is truly interested, then he may bite. If he’s playing around or you’re being too subtle for him, he may not.

You can also subtly call him on his antics:

YOU: Gee, you know, you asked me for the menu from the local diner, but you haven’t been there have you? I was wondering why you wanted it?

You’ll be pretty safe asking questions. You can also give genuine compliments. For example, when I first met my dream partner, James, I noticed his beautiful smile. So I complimented him on it. I wasn’t trying to flirt. I was just appreciating his beauty. Well! That really got his attention because apparently, he had no idea that he was good looking! Amazing isn’t it?

So find something genuinely interesting or attractive about the New Guy (assuming you ARE interested in him) and share your appreciations. It can go something like:

YOU: You know what I appreciate about you New Guy? You have the warmest smile/greatest laugh/very attractive eyes.


YOU: You know what I appreciate about you New Guy? Whenever I see you, it makes my day because you really know how to make me feel comfortable/make me laugh/ make me smile etc.

OK, enough flirting lessons for the day. The bottom line is this: you’re going to have to stretch a little out of your comfort zone to test the waters. It doesn’t mean that this guy is THE ONE you’ll spend the rest of your life with, but every relationship helps you learn more about yourself. Let this relationship be a springboard for your personal growth.

Happy Flirting, (and tell us what happens!)
Dr. Karen Kan

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