The question

I am a bit sad these days because my girl is always hanging out with her best friend (male) and actually, in the past, they used to date each other. This makes me get angry at her all the time. How can I trust her? In my mind, the thought is always the same: that her "bestie" is going for another try. What should I do?

The answer

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There's a complicated answer to this deceptively short and seemingly simple question.

Basically, it depends on a lot of factors.

But first, allow me to issue a caveat: As time has gone on, I've started to surprise myself by how conservative I seem to be getting on these matters.

A recent Washington Post article mentioned that Vice-President Mike Pence wouldn't dine alone with a woman other than his wife – a marital detail that sent the Twitterverse into a tizzy of frenzied thumb-typing.

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Not just Twitter: Talk-show host Trevor Noah called Pence "Sharia Mike." Many pundits, critics and talking heads opined he was setting the feminist clock back to the dark ages. What if a woman on the team – say, Ivanka Trump (interesting choice, I thought) – wanted to discuss business over dinner? One employment lawyer wondered aloud if Pence's "policy" might even be illegal.

But I liked it. Pence said, "It's about building a zone around your marriage." And, personally, I get that. Adultery is a slippery slope, a series of incremental decisions. E.g: 1) "I'll go out with that sexy intern, but only with a bunch of people around"; 2) "I'll go out alone with the sexy intern, but I won't go up to his apartment"; 3) "I'll go up to his apartment, just for a quick drink, but I won't have sex with him" – at which point, of course, you're pretty much sunk.

Mike Pence is simply declaring he won't even get on the chairlift leading up to that slippery slope.

Anyway, this is all just to say I may be more old-fashioned than some.

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To be clear: I'm not saying you should attempt to restrict your girlfriend's activities in any way. And I most certainly am red-flagging and pooh-poohing you saying you get "angry" at her a lot. Both those retrograde notions are out.

I do think you should do a gut check. Do you feel insecure about her faithfulness?

I hope this doesn't seem contradictory to what I said above, but I have many female friends and will go out alone with them. Doesn't bother my wife a bit. In fact, I could probably be nude in a hot tub sipping champagne with Christina Hendricks, Sofia Vergara and Ivanka Trump – and my wife, passing by, would just inquire: "How's the water?" Maybe ask for an autograph or two. (None of us would have a pen, unfortunately: nowhere to stash it.)

Why? Because she knows I am and will always be as faithful to her as the day is long.

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(An odd expression, I know: What happens when the day is over? What I mean is I'm faithful.)

I wonder why you don't trust your girlfriend. Do you feel like she gives out "the single vibe" with this guy and others? Or perhaps you trust her, but not him?

Also: Do they do a lot of romantic-type things (picnics, ice skating, etc.)?

And, finally: Do they invite you along? Maybe Trevor Noah would call me Sharia Dave here, but I feel like it's common courtesy to invite both parties of a couple.

I know you can't answer these questions. But these are the "factors" I mentioned earlier. What you should do depends on them.

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Put the questions to the man in the mirror. If you believe there is good cause to be jealous, by all means, tell her how you feel. Say something to the effect of, "Listen, your relationship with your ex is setting off alarm bells."

And talk about it. If she's reasonable, she will see reason. Maybe curtail some of the cutesy tête-a-têtes.

But, as I say, at the same time I would be wary of either getting mad at her or trying to restrict her activities in any way. It might have what I call the the Wet Bar of Soap Effect: The harder you try to squeeze her, the more likely she is to slip out of your grasp.

Basically, anger isn't sexy. Jealousy isn't sexy. Confidence is sexy. Maybe if you exude more of it, she'll decide on her own to stop playing with fire with her ex.

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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