Dear Penny

Dear Penny: Should I stay friends with the married guy who tried to sleep with me?

Whatever you do, don't follow Don Draper's example(s).
Whatever you do, don’t follow Don Draper’s example(s).

Dear Penny,

Recently I got propositioned by a friend of mine who is married (and not one of those open marriage situations). We’ve known each other for many years, wherein no “lines” were ever crossed besides some friendly flirting. When I said no, he backed off, but I’m still feeling unsavory about the situation. It feels like a betrayal of trust and friendship, besides all the skeeviness. Do I cut off the friendship, or pull a Don Draper and pretend it never happened? I am friends with some of his friends, so it complicates things… even though it’s not my fault, we all know what people will assume. Also, Lemonade JUST came out and he has to know I’m listening to that on repeat. Come on!

Not Becky With The Good Hair

Dear Not Becky,

Don Draper did a lot of things on Mad Men. As a married man putting the moves on you, your friend definitely pulled a Don Draper, and you know that old adage: two Don Drapers don’t make a right. So, whatever you do, don’t use him as a role model, especially in this situation.

Anyway, your friend betrayed you and betrayed his wife, so there’s no doubt he acted skeevily. But that doesn’t necessarily make him a horrible human. We’ve all exercised poor judgment at one point or another, and his actions in a moment of poor judgment should not be the downfall of your friendship. It’s rather how he chooses to behave now, in the aftermath of your rejection of his advances, that should determine if your friendship is worth salvaging.

Is he treating you any differently? Do you feel respected? Can you trust him again?

You need to evaluate the years of your friendship with this guy and decide if the relationship’s past is worth its future. You seem to imagine only two options: end the friendship, or pretend it never happened. But there is a third option: talk to him about it. Yes, it will most likely be an uncomfortable conversation, but it’ll help you decide whether his friendship means anything to you, and how you can move forward. (Neither of you can ever ignore that a line was once crossed, so while pretending it didn’t happen just to keep the friendship alive might seem okay now, it will strain the relationship in the future.)

If you’re able to talk to him about what happened and why it happened, you can both gain some closure — regardless of whether you ultimately decide he’s no longer your friend. Yes, we all make bad decisions sometimes. And we should strive to be the kind of friends that warrant forgiveness when those bad decisions come to light. Ask yourself: is he that kind of friend?


Readers, weigh in: have you ever dealt with this situation? Share your own advice in the comments! 

Dear Penny is written by Margaret Bortner. Follow her for more life advice: @askmemargaret.

And do you want advice from Dear Penny? Send her your questions about brokester etiquette, dating, awkwardly splitting the bill and anything else at [email protected]. We’ll keep you anonymous (or give you a shout out on social media if you like). 

Leave a Reply