Should You Tell Your Boyfriend Who You Slept With During a ‘Break’?


Welcome back to our GuySpeak/GirlSpeak rubric. Over at Loveawake, girls write in and ask real guys real questions. Together, at Loveawake we pick one of the questions and each answer it the only way we know how … the right way. Sometimes we agree, usually we don’t. This week’s question:

This week Alex and Emily help a woman with a guilty conscience. Does what happens during a break stay in the break?

Guy Voice: Alex Wise

At the risk of sounding like the biggest d-bag in history, I’d say that there is absolutely no good reason to tell your boyfriend. That is, of course, if two basic tenets hold true:

1) You won’t ever do it again, and the romance with the friend has totally died down, and 2) you’re sure his friend won’t tell.

Let’s assume that they do hold true. What, then, is the point of telling your boyfriend? You two were broken up. YOU WERE ON A BREAK!!!! (Word to Ross.) Telling your boyfriend about an indiscretion you had during a three-year hiatus is pointless. You both probably did things you aren’t happy about and that led you back to each other. Divulging to him that you slept with his friend will only destroy your relationship because he will never trust you. For some reason, knowing that your friend has seen your girlfriend naked does terrible things to a man’s psyche. Call it pride. Call it hubris. Just don’t call Tyrone.

Additionally, telling your boyfriend is something that you would do to make yourself feel better. It’s not about him — it’s about clearing your own conscience. Clearing that air doesn’t make things better. It will ultimately wear down on him until you break up. I assume that his friend hasn’t told him, or you two wouldn’t be back together after all this time. While most people think that clichés are, well, cliché, they exist for a reason. With that said, ignorance is bliss.

When you and your boyfriend got back together, I presume it was under the auspice that everything prior was water under the bridge and you intended to move forward. To me, that includes everything that happened before you two made that vainglorious decision to be an item again, which in your case is a total mulligan on sleeping with the friend.

Which brings me to the friend: ewwww. What kind of “friend” sleeps with his homie’s ex-girlfriend? What a douche. I think that you should have a conversation with him to make sure that you all are going to agree to keep it to yourselves because THAT’s where it becomes an issue: the jealous friend decides to destroy your relationship, then you come out as the liar and manipulator. But like I said, he hasn’t said anything yet, so I’m guessing he doesn’t want to lose his friendship either.

At the end of the day, you made a mistake (and it’s only a mistake in retrospect, given your current status with the boyfriend). It’s not his business unless you both decide to divulge any dalliances you had, and if you’re over the age of 22, why would you even do that? In the famous words of rapper / philosopher king T.I., keep it moving. What he doesn’t know what won’t kill him. Thank you, and good night.

Girl Voice: Emily Gordon

The rulebook of Sex and Exes dictates that once you break up with a man, his friends are fair game to you. However, the Sex and Exes book also says that if your friend breaks up with someone, that ex is NOT fair game to you, so technically this foul was on the friend. But this matters very little: The bad news is that you have to tell your reboyfriend about this. The good news is that if you guys have decided you should get back together after three years of being apart, you’ve probably thought it through, and a thing like this will just be a tiny speed bump on your way.

Now I know a lot of you (including you, Alex!) probably feel like it’s none of this boyfriend’s business what you were up to during a three-year break, and you’re totally right. I mean, three years ago we still had W as president and Avril Lavigne had a hit song. Telling your boyfriend you slept with his friend isn’t about trying to atone for your sins — it’s merely an act of cleaning house.

The fact is, at some point in time, your frowned-upon nookie will come to light. Period. Stuff like this always comes out, and wouldn’t you rather be in control of how it does? It will always tickle the back of your mind, it will always be the first thing you think of when he says, “Hey, can I talk to you about something?” and if he still hangs out with this friend, you will always be terrified that they’ll get drunk together and the friend will spill the beans, leaving you looking like a secretive slut.

My advice to you is this: Let the Friend know that you’re planning on telling Boyfriend about the tryst (and, please, keep it businesslike!), and then immediately tell Boyfriend so that Friend doesn’t beat you to it. Sit your man down, look him in the eye, and perhaps start the conversation by saying that both of you probably did things you weren’t super-proud of while you were apart. Tell him that you respect him so much that you feel the need to be honest with him about something you did. Then tell him. Spare the details, just keep it dry and factual.

Be ready for him to be furious, miserable, and betrayed. If this friend is still in your social lives, be ready with some ideas on how to set boundaries that will make Boyfriend feel comfortable. Try to not say, “But we were on a break!” even though this is both true and will make you sound like Ross, it’ll also just make it seem like you’re making excuses. Make it clear that you are telling him this out of respect because, truthfully, this shouldn’t destroy any trust the two of you have — he was your ex when this happened. This is more of a matter of disclosure and respect, and once your new/old boyfriend gets over the initial shock, he’ll see it that way too.

This may be one of the reasons my mom always said, “An ex is an ex for a reason.”

Photo by Joshua Ness on Unsplash