Dear Wanda and Wayne,
I recently started casually dating a close friend's ex-girlfriend. I brought up the possibility to him of me asking her out, and he seemed amazed that I would even consider it.
The problem is that I didn't tell him that we had already been out on a few dates. I just assumed he'd understand -- they'd only dated for a couple months. Now I feel like I have to choose between breaking things off with a girl I like or breaking things off with a good friend. Can't I have it both ways?
Wanda: Yes, you can have it both ways -- if your friend stops acting like a proprietary poodle who's pouting about another puppy peeing on his fire hydrant. I'm in your corner, BFF.
Anchorage is small. Alaska is small. Populationwise, we simply don't have the options one enjoys in Seattle, Chicago or New York. My feeling is, if a casual and temporary encounter with someone doesn't click and progress, for goodness sake, release him or her back into the pool so they may live to mate and spawn another day. I'm mixing lap dog and salmon metaphors, but you get the point.
The idea that this woman is now off limits to all your buddy's friends because his short-lived deal with her didn't pan out -- ridiculous. And selfish.
A close friend and I recently debated this: Is it OK to date someone a friend has also dated? His perspective was refreshingly altruistic: If you really care about the person, don't you want him or her to be happy? And if that means happiness with someone else, shouldn't you support that?
Yes. It does hurt when someone we have cared for finds someone new -- and it's someone we know. But here's what we forget: This too shall pass. It hurts now. But life goes on, and the people with whom it didn't work out, well, it becomes less and less a big deal.
If your friend had been serious with this woman, my response might be different. As it is, I think he needs to take the high road and give you both permission to be happy. Isn't that what everyone deserves?
Wayne: You really are a close friend! So close you could take notes of this lady's likes and dislikes during their relationship. So close you probably had to run out of the room to make a silent fist-pump after your friend told you about the breakup.
You aren't a friend -- you're a lazy, opportunistic weasel. At a time when you should have your buddy's back, you're sneaking around behind his back with his ex. And you asked him how he would feel about you dating his ex after you're already dating her? That move sealed your Friend of the Year Award!
Wonder how Wanda and her homegirls would feel if their altruistic buddy started seriously dating one of you, then moved on to the next? No biggie, right -- everyone would just want everyone else to be happy. Yeah. Emotions, love, friendships -- those things are never complicated.
Wanda is correct that Anchorage is pretty small, so small that these two won't be able to move around without bumping into mutual friends who say, "Can you believe he's dating the same girl that dated (insert your close friend's name here)?" Oh BFF, you think you and her can just drop right into the social circle and not have things be weird? You really are clueless.
Anchorage isn't so small that you can't find a date. There are hundreds of local singles online at this very second who aren't already attached to your social circle. But that would be too much work.
You know what is really small? The circle of really good friends you'll have in your lifetime. Yours just got smaller. Enjoy your time with this amazing lady -- you deserve each other.
• Wanda is a wise person who has loved, lost and believes in retail therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at firstname.lastname@example.org.