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The question

I'm one of those people to whom life has dealt out large dollops of good fortune: a steady job, good health, and an incredibly beautiful and patient woman in my life. Let's call her DG ("Domestic Goddess") for short. Over the last seven years at my job, I have become particularly good friends with one of my co-workers – a brilliant, cheerful and wonderfully sympathetic individual, the kind of person who lightens everyone's workload just by showing up. Without a doubt, AW ("Awesome Woman") is my best friend after DG herself. My problem is that my only contact with AW is through work. I wish we could do other fun "buddy stuff" together (for example, we both like bicycle touring). However, I am so concerned about even the possibility of a misunderstanding that I have never been able to raise the subject with her. I suspect one standard solution would be to arrange "couples" get-togethers with AW and her boyfriend (I've only met him once, but think we'd get along well). The problem with that idea is, they live in one city, DG and I in another (the workplace is more or less in-between), so getting all four of us together would be a challenge. I really don't know what, if anything, I can do. Is being friends with a female co-worker too much to ask for?

The answer

Pal: Who are you trying to kid? Me? My readers? Your wife?

Yourself, mostly, it seems to me.

Hmmm, I sense a "teaching moment" here. See, people, this is how it goes: You start by deceiving yourself, and end by deceiving others.

Or is it the other way around? Either way, you'd be surprised, my smug-sounding friend, how quickly an angry God or vengeful ex-wife can swallow up your "large dollops of good fortune."

A friend of mine, who like you has had "large dollops of good fortune"– ray-of-sunshine wife, healthy and happy brood of kids, money to the ceiling, stately domicile – but shares with me a healthy dose of what the Brits call "tramp dread" (fear of becoming homeless) has always said: "I'm only ever six bad decisions away from living in a refrigerator box, Dave."

He means six poor decisions, which in his mind would unfold something like: 1) tongue-lash boss, get fired; 2) invest nest egg in Bernie Madoff-type Ponzi scheme; 3) drown sorrows in drink; 4) in boozy frustration, begin to browbeat and berate wife …

You get the idea. I always say: "Six poor decisions? Luxury! I'm only ever one or two poor decisions away at most! In fact, I might make all great decisions and still wind up on the street!"

My point, sir, is it seems to me that you, in a fog of self-deception, may be on the verge of making an unwise decision that could have a negative impact on your oh-so-wonderful life. Here's how these cases of delusion tend to unfold:

It starts with, for example, a cozy little bike ride. What'd you call it? Oh yeah: "bicycle touring." You tell yourself: "I'll go bicycle touring with her, but I won't take her out to dinner." Then: "Okay, we'll go out for dinner, but I won't go up to her apartment afterward." Then it's: "Okay, I'll go up to her apartment, but just for a quick nightcap. No sex, ha ha – obviously! Duh!"

And winds up with your wife thumbing through the Yellow Pages looking for – oh, wait, people don't do that any more. Let's say: typing "lawyers + divorce" into her Yellow Pages app.

Now, you may howl in protest: "Dave, you got me all wrong! I have searched my soul and can honestly tell you I have no intention of cheating on Domestic Goddess with Awesome Woman."

(I'm barfing into my mouth a little at all these nicknames, btw. And while it's nice you call your wife a goddess, I wonder if she feels so wonderfully about the "domestic" bit.)

But if that's the case, what's all this mumbo-jumbo about a four-way get-together being "difficult to arrange"?

Also, methinks I doth detect a bit of a protest-too-much snake in the tall grass with your hand-on-heart declaration about how well you'd get on with her boyfriend.

You want to get along well with your co-worker's boyfriend? Here's one idea: Don't invite his girlfriend out for private little tête-à-têtes.

If you would truly like to be friends with your co-worker, go the above-board route: Invite both her and her boyfriend to your house or out for drinks or dinner. Introduce Awesome Woman to Domestic Goddess and take it from there.

I'm sure if your co-worker and her boyfriend are likewise interested, they'll be up to the "challenge" of travelling from one place to another to get together.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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