Dibs and Digs 

Hey McGuinty!

I recently ran into a business associate and discovered that she divorced her husband a year ago and has moved a few minutes from my house. She is totally amazing and someone I was attracted to immediately. It was obvious that she was attracted to me too, and she confided in me that the divorce is not generally known outside her closest friends and relatives. I'm thinking seriously about asking her out. There's one small problem: Her ex is someone I run into at industry events and count among my business associates. That makes this situation somewhat ticklish and makes me wonder: Is it ever cool to date the ex of a friend, relative or business associate?

— Attracted to Associate

ATTRACTED!

It does sound like she wasted no time in telling you of her divorce, doesn't it? And hey man, that's cool. It's been a year and she's giving you the green light. I think you should proceed, but with caution.

Your question is phrased in a very broad way, and there's no one blanket answer that covers everything. The fallout from dating the ex of a friend, relative or business associate varies greatly. Should you ever date your brother's ex? Maybe if you're already not speaking to him, sure, but probably not if you still want to have the cousins over for that annual Easter egg hunt.

Is it cool to date your friend's ex if that friend got divorced 15 years ago and is himself remarried? Potentially. But what if it's only been two years and he's still in love with her? In that case, it depends on how much you want to stay friends. If you truly do, you'd be wise to hang back. That said, dude can't call lifelong dibs on another human being that doesn't want to be with him. See how many shades of grey there are?

In your case though, I'd say you're fine. Your description of this guy isn't evoking images of bro-hugs when your team wins the playoffs. You run into him at industry events and call him a business associate. You don't owe him loyalty if you can't even call him a friend. Will he be pissed? Who knows. Will it be awkward the first time you see him at a ribbon cutting? Maybe. Or maybe he's moved on too, is a total grown-up and is glad his ex is with someone sane and stable. Don't bring the lovely lady to events where you'll see him, and you should be cool.

Hey McGuinty!

A few months ago, I went on a diet and exercise program and it's really working. I've lost a good amount of weight, I feel better and I look a lot better. I'm also in a long relationship that is committed and happy. I have longtime friends — lovely, well-meaning people — who are telling me that I've got to be cautious, that I'm going to be furiously hit upon, and that nothing has prepared me to resist this kind of onslaught.

I've laughed it off so far, but it keeps happening. I don't know whether to be grateful or pissed, and I sure don't know how to respond to my nice but aggravating friends. So McGuinty, what's your take and how should I respond to my friends and their warnings?

— Samoa Slim

SLIM!

My guess is your friends are pretty good at tennis, because they sure can serve up a backhanded compliment. Jeez.

That's one potential response right there, one that would hopefully let them know in a sarcastic-yet-friendly way that they've said too much and should stop talking. I'm with you on the mixed feelings, though the more I think about it, the more I lean to the pissed end of the spectrum. It's fine to acknowledge and commend someone's weight loss efforts but to imply that they're only now going to be attractive to other people is extremely offensive and just completely untrue. Not to mention, I'm sure you've been hit on during the course of your relationship and I'm sure you handled that just fine. I have no doubt that you'll continue to do so post-weight loss. Yeesh.

If you're feeling particularly feisty and want to get your message across in a less polite way I'd go with the classic, "Thank you and fuck you." Say it with a little smile, a slight glint in your eye, and they'll get the message loud and clear that they've crossed a line.

Jessica McGuinty, founder of Jessicurl and master of the joyful laugh, doesn't really think she has all the answers — but she'll give it a try. Write her at [email protected].