Hello again gents,

So I've found myself in a bit of a pickle and I'm not too certain how to go about dealing with it.

So the back story is I was in a relationship for going on six years, two of which I was married to this lady. Well a few months ago the relationship started dying (I'm sure there's reasons linked to living together full time) and it turned into a friendship/ room mate type of deal. Around a month ago we mutually decided it wasn't working and we started the legal separation process. Now there is absolutely no chance of this marriage working out as honestly this has been a recurring event throughout the entire relationship and I'm personally done living that kind of life.

Since we separated my life actually got better, I was allowed to be myself again and that really opened up the road to personal progress.

So here comes the dilemma... Recently a new lady started at work and I have taken quite the liking to her, she has an extraordinary personality and I feel such a strong connection to her. I have absolutely no idea if she is interested in me at all and I don't have a clue as how to find out, you know six years not even being interested in other women then all of a sudden this happens. I was intending on asking her if she would like to go for coffee this weekend today but I bailed hard on that when in passing she said she wouldn't get involved with someone she works with. I guess what I am asking is first of do you gents think the women who say 'I couldn't get involved with someone I work with' can be converted because personally I don't believe the whole not trying with work colleagues because just because you work with them doesn't mean things can't work out. Secondly how should I go about finding out if she is interested in me at all?

Thanks in advance gents,


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do you gents think the women who say 'I couldn't get involved with someone I work with' can be converted

Sure, but you shouldn't expect it, or count on it. Ultimately your thoughts on the matter don't matter as much as hers. This could, of course, be a defensive statement on their part indicating a wish to stave off *any* relationship enquires (off the market, for whatever reason). You can make your interest known, but will need to respect her wishes on the matter. 

Secondly how should I go about finding out if she is interested in me at all?

Same way as always. Ask her if she'd like to get coffee, or lunch, or see a gallery opening, or something. Then talk. 

I don't know how things work in the Commonwealth, but the States-side zeitgeist is pretty unanimous: separated = married, and needs to be disclosed before or at the very beginning of a first date

Thank you both for quick replies,

Liam, thanks again I fully agree with what you are saying I have no expectation what so ever and I have no intention of pressing the matter should there be no interest. Honestly for the time being at least I am more so looking for a means to get to know her better as a person, she is also new to Ottawa so we are both in the same boat as far as that goes. I guess I will just ask her if she would like to do something casually where I could possibly make my feelings known if I don't feel like it would make anything awkward and uncomfortable that would be the last thing I want to do.

Rebekah, thank you for the reply. I believe it would be the same in the Commonwealth but I am not 100% sure but alas it does not matter for as I had stated in this reply to Liam I am more so looking for a 'get to know you' date if you will. I have every intention to discuss and explain in whole that part of my situation. There's no sense in lying or hiding anything, that does no one any good.

Kind regards,


Hmmm...the context of how she said that "in passing" would help. But it sounds like you could be setting yourself up for a "you're such a good friend" kind of conversation from her.

Maybe just take a few weeks or months to get to remember who you are first?

Failing that, just walk by her desk, say "going for coffee, you in?" sorta non commital-like....

Good luck either way!

Definitely let her know you're technically still married.  The sooner the better.  I actually think that may be a higher hurdle than the co-worker thing.  You may have to wait until its official.


As for her 'rule' ... its easy to have a blanket rule like that when nobody's asking.  There's only one way to find out if you're the exception.


Only way to find out if she's interested is to ask her out for lunch or something.


Thank you for all the responses guys,

Today I did what I believe was the smart thing and I held back, I decided just to talk to her at work explained the marriage situation which didn't seem to bother her at all she was more so concerned if I was financially able to cope lol. I found out shes moving away again in July too so I'm not sure what to think about that but right now I'm thinking nothing of it. As for the 'wont date co workers' (context was in a passing conversation about all the couples working at the company) thing I don't think that will be an issue as I intend to leave the company as soon as I have my P.I. license and a job in the field which should be in a month or so (also explained this today). Anyway I have decided the best thing to do will be just chat to her at work see how things go for a while then maybe ask her if she wants to go somewhere at a later date.

All in all it seems we get on real well, there's been a lot of 'Can you keep a secret' and 'We would do this better' 'We would make a good team' comments from her I may be wrong but all that sounds kind of friendzoned material to me lol.

Regards fellas,


I guess what I am asking is first of do you gents think the women who say 'I couldn't get involved with someone I work with' can be converted because personally I don't believe the whole not trying with work colleagues because just because you work with them doesn't mean things can't work out.

Respect her stated wishes, without necessarily holding her to them. Beliefs are extremely superficial.

Secondly how should I go about finding out if she is interested in me at all?

Don't ask her out unless she explicitly changes the rules. But, if the right moment came up, you could say something like

"I think it would be fun to .... and I'd like to ask you if you'd like to join me, but I won't because I don't want to put pressure on you, because I remember that you don't date people you work with".

But you have to say it like you mean it, very casually (just like she told you she doesn't date people she works with) not like you're being coy, even though you're being coy. Anyway, bringing the subject up, while nixing it, will have the effect of making her conscious of the possibility. If she wanted to go out, she'd find an excuse to make an exception to the rule. If not, nobody loses face!

Honestly I understand exactly where you are coming from but if I were in your situation I wouldn't go after the coworker just yet.

You just got out of a relationship, there is a lot of truth to be had in the fact that humans tend to seek confirmation of their attractiveness/desirability in a "rebound" relationship immediately after the disintegration of a long time love.  My advice, be friendly, be fun, be professional and seek your rebound elsewhere.  Reconnect with friends, get out of the house and just socialize with mixed company.  Don't put any pressure on "picking up" a girl.  Just be a cool alpha dude who emulates warmth and calmness. Women will respond to that better than any pick up line.

Once you have a plethora of "options" in your life you can revisit the attractive coworker and decide objectively if she is the one you want.  If she still is, proceed with caution. Coworker relationships do work and I am sure we all know a married couple or two who met through work but for every success there are 10 failures.  Just try googling, "ex and coworker"

Best of luck in the hunt. When in doubt about how to react to women, stop, breath, and ask yourself If this was a James Bond movie and I was James Bond how would I behave.  It sounds stupid but it works.

She already gave you her answer.  She wants to keep her business and personal life separate, and she wants her business associates to be her business associates.  The cards are off the table; she's just not that into you.  She wants professional relationships with her co-workers, and she doesn't want to complicate that with love and sex.  I find this very admirable for her to take this stance, because she has a lot of respect for herself to do that.

You, too, need to respect her.  Don't try to "convert" her, or otherwise control her in any other way.  You'll only bring tragedy to yourself, and to her.  If you had even an ounce of respect for her at this point, you wouldn't even consider pushing an unwanted relationship upon her.

She's not interested.  Move on, find a better woman for yourself elsewhere.

Thank you for all the replies,

There seems to me a lot of mixed opinions about this subject both within a community and within ones self which makes it difficult to figure out what is best, I think my best bet is to take a little bit of every opinion and create some sort of conclusion from that.

So I've decided I will not pursue her just yet thanks to Sean Michael Bach for that as you made me realize I do respect her a great deal and its not for any comment she has made or any stance per say its because of who she is. Also thanks to D Whaler your response made a lot of sense to me and also helped me come to this conclusion.

I'm not really concerned about the 'will not get involved with 'colleagues' comment as in April/ May I will be leaving the company and we would therefore no longer be colleagues anyway, I do however wish to socialize/ get to know her outside of the work environment. I'm wondering if it is then acceptable to ask a colleague if they would go for coffee with you for the purposes of getting to know them outside of work? If that was to happen and things clicked would it be okay to openly discuss your current feelings as long as you explain that you would like to wait it out a little longer to make sure your feelings are true?

I'm wondering if there is a way to have a conversation where you are able to subtly drop hints that you are interested without risking making everything awkward, Ideally thanks to all you gents and lady I feel what my ultimate goal would be is to go for coffee and get to know each other better, discuss feelings and such, wait around just being casual friends and colleagues until I leave the company, possibly give it a little while longer in case I'm still not fully over the divorce then if my feelings for her are still there speak to her about it then.

Side notes: The comment about not getting involved with a colleague wasn't said to me I just happened to hear it.

So gents, thoughts on the casual coffee conversation idea?



Well, the dynamic certainly changes if you're no longer co-workers, doesn't it?  If you never have anything more to do with her in the business world, I don't think it's at all out of place to directly ask her for a date, provided that you're no longer working with her.  That's her rule, after all; she doesn't date "someone she works with," and since you're no longer "someone she works with," an potential opportunity to date this woman appears, provided that she agrees with you and no longer sees you as a business associate.  

It never hurts to ask, when that day comes.  Just flat out ask her, "I'm no longer working with you.  Would it therefore be appropriate if I were to ask you out on a date?" Then she will say yes, or she will say no, and you will be happy to have settled the issue in either case.

I say go for it. If you are leaving the company you have nothing to lose.

Start a platonic conversation about something non work related that she is into. After a bit say something like this: Hey ______, you seem really cool. I'm thinking of checking out at this cool coffee shop down the road tomorrow afternoon (be specific with a place and time, choose an interesting coffee shop) why don't you come with me, I would like to hear more about ________. (hopefully there is a hobby/trip/interesting thing about her that you can insert here)

Expect her to resist, don't let it phase you. If she says she's busy you can suggest another day but avoid begging at all costs.

Her: "Oh I can't tomorrow....I have blah blah blah..."

You: "That sounds really cool....(ask follow up questions about blah blah blah to keep the conversation rolling).  I could switch the coffee adventure to  _______ if that works better. (again be specific with a date/time)

If she resists again without countering with a different suggested date/time cut your losses.  Say "That's really too bad, I was hoping to get to know you better. We'll see you around."  and walk away.  You must be willing to accept that she honestly isn't interested.  Keep being the cool fun professional guy and try interacting with her a few times per week in a friendly way. If you feel she is warming up try suggesting another after work date (different than coffee, maybe a glass of wine at a cool pub).  If she shoots this down scratch her from the list permanently. 

Warning: normally I would suggest being a little bit flirty-sexual in your interactions but at work absolutely do not be sexual at all. No innuendos, no sexual joking, no sexual teasing, nothing. That's just one misunderstood comment away from being a harassment case.

On the date you want to frame yourself as a romantic partner to avoid the friendzone but that's a whole other topic.


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