Hi Guys,

I have wondered about the question above, since I’ve been divorced for six years.  There is a man that has been coming into my work center for a few years now. We engage in the normal pleasantries and for the past six months he has been very
attentive to me. He lives in another state. We don’t talk long, as he has to prep his work area down the hall, then leaves on a flight.

He always comes to my area, smiles, jokes around and asks what my plans are for the weekend; the next week he asks if I did the activity I planned. He says some really sweet things like it made his week to see his favorite agent, or it wouldn’t be worth coming here if I wasn’t there. He is not afraid to be vocal when he says these things. A lot of people won’t give me the time of day due to my profession, but he isn’t afraid of speaking or being seen with me.

I don’t know if he’s married, no ring, but that doesn’t mean anything. I am very shy and am not good at flirting but I tell him how nice he looks etc. We just click and I think I have a bit of a crush on him. I was thinking of writing a short note to tell him how much I admire him and the aforementioned qualities. I don’t want to hurt our passing friendship, so I won’t say how I feel when I see him. I really don’t know what to do and I don’t want to read anything into it but that he just like teasing me, for fun.

What do you think I should do? Should I let him know by note that he’s a wonderful person or is that going to make him
uncomfortable?  I don’t ever want to do that. How do you tell? It seems like such a fine line.


Dear Ann,

Thanks for your question. Now you got us curious. What do you do for work? (Can you even tell us?) Why would people not talk to you because of it? (And it’s a good sign that he does.)

You are so right when you say this is a fine line. It always is. The fact that these interactions are happening at work is also factoring into the equation. It’s one thing to ask a woman out at a bar, it’s quite another to ask a woman out at work—even someone you work with occasionally. It’s all about implications and consequences. It’s one thing to get rejected at a bar, it’s quite another to have a work relationship blow up in your face. So as we answer your question, this variable has to be considered.

Ann, it’s time to be a detective. It might help your decision if you knew more about this guy. Is there anyone you can ask? Can you google him? The other way to glean information is hint around without actually saying it. For example: After he asks you what your plans are for the weekend, you could say something like, “So what are you doing this weekend? Are you taking your girlfriend out on the town?” You can get away with this if you say it in a flirty, joking kind of way. (We know you say you aren’t great at flirting, but we’re confident you can do this.) Based on his answer you will probably learn a lot. You might say to yourself, “Well, won’t it be obvious that I’m sniffing around?” And our answer is: Yes. But that’s not a bad thing. He’ll get a better sense of where you stand. So instead of writing him a note telling him how you feel, start by doing it in a circuitous, flirty way. If you learn he has a wife or serious girlfriend, then you’ll know his visits are strictly friendly. And if they’re not, then you’ll learn something about his character because that means he’s being deceitful, and trying to cheat on his partner.

The other tricky part of this is the fact that he lives in another state. He might be very interested in you, but not be interested in a long distance relationship. But if he got to know you better, he might change his mind on that. So question for you: What time of day does he come in? Would it be possible to take your break around the time he visits? Or go to lunch? We see no reason why you couldn’t ask him if he’d like to grab a coffee, or go to lunch. Yes, it might be a little forward, but it would break the ice a bit. And once you were away from your work environment, both of you might open up a bit.

If none of our suggestions work, and you’re still feeling like you want to reach out to him, then yes, a short note revealing your feelings would be okay. And if he doesn’t reciprocate, well, then the fact that you don’t see him that often will actually play in your favor because he won’t be around every day to remind you of the rejection.

So start by trying to investigate a little and see what happens. Be patient. Give this another month or so, and if things don’t progress with Plan A, go to Plan B. But remember, once things get rolling, he needs to be the one to take the initiative. It’s okay to break the ice, but after that, he’s got to be the one making the moves. (Asking you out on a proper date, etc.) Otherwise you’ll still be wondering where he really stands.

We hope this helps. Ask as many follow up questions as you’d like. Now, or a month or two from now. Leave us a comment/question in the comments section below.

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Good luck,


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