Ask Him: My Friend Is Engaged…And Dating

NOTE: Scott changed all of the names in this piece to common stripper names, to protect the anonymity of affected parties and also for fun.

Q: My friend Candy messaged me the other day asking me what I thought about a guy I know named Justin Timbersnake, because she had just gone on a date with him a few nights before. Thing is, Timbersnake is engaged! I just confirmed this with a mutual friend, and speaking of friends, I have more mutual friends with Timbersnake than Candy, and I don’t want to cause a rift with any of them. I also don’t want to see Candy or Timbersnake’s fiancée get hurt. I haven’t responded to Candy yet. What should I do?


A: I must say that you are in quite a pickle. I do not envy your situation—to be caught in a moral dilemma like this where you care about the parties involved on both sides of the metaphorical coin and where your own social standing may be influenced by your decision is never an easy thing to deal with. And before I get started, I should say that my advice may not be the best for you to follow. It’s impossible to know what to do in a clusterf**k of this magnitude. You’re in a situation where no matter what you do, you’re probably not going to feel like a winner. So, at the end of the day you have to follow your heart. I guess.

But of course you can’t ignore something like this. If you were to not respond at all to Candy, she would take your silence as reason for alarm, or she would think that you didn’t care enough about her to give her a quick Yelp review on a guy you knew who was attempting to woo her.

If you sounded the alarm to all your friends about Timbersnake venturing away from his—I don’t know, whatever snakes live in—then you might be viewed as a rattle tale, which could result in you being uninvited from the wedding, leaving you one Save The Date fridge magnet away from a full summer collection.

There’s also the possibility, however unlikely, that Candy misconstrued a simple business meeting as a date, and if this were the case and you sounded the alarm, you could unjustifiably ruin lives, leaving you to feel responsible years later when Timbersnake, in his despondence following his broken engagement, relocates to Alaska to become a crab fisherman and his boat capsizes and he drowns.

So here’s what I think you should do:

Reach out to Timbersnake and fill him in on the situation you have unwittingly and unwillingly found yourself in. Ask him first for an explanation, and then tell him that you will tell Candy he is engaged if he will not, and that he better have a fantastic reason for you not to tell his fiancée that he’s been tryin’ to line up a little something extra on the side behind her back when they are in the midst of planning a wedding.

Give Timbersnake a timetable in which to tell Candy that he is engaged to be married, and tell him that by the deadline you must have heard from both himself and Candy, by voice or FaceTime, that things have been explained, that there is an understanding, that nobody is going to be murdered, nobody is going to be blackmailing the other party, et. al.

While you wait to hear from Candy and Timbersnake, you may want to relocate to an unexpected and undisclosed location. I hope in my heart of hearts that Timbersnake wouldn’t do anything drastic and barbaric, but I’ve also seen enough Lifetime movies to know that you can never, ever be too careful.

If you do find yourself having to tell Candy and the fiancée that Timbersnake is “a real snake, all right,” then try your best to be there for both of them, and rest assured that you ultimately did the right thing. A guy who is cheating on his fiancée before they’re married should always be called out.

Cheating is not cool, y’all.

And if you know where snakes live, or have better advice, lay it on Candy in the comments.


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