Dear Winnie, I think my best friend’s boyfriend is cheating. Should I tell her? Meddling in a friend's relationship is often a no-win situation, says Winnie

Dear Winnie,

I hate my best friend’s boyfriend.

I’ve never gotten on with Zul. Initially, I thought I hated him because I was resentful that he was taking time away for me to spend with my best friend, Iman.

But even though they’ve been dating for quite sometime, a couple of years, I have never changed my mind about Zul. I detest him still, even after making efforts to spend more time with the couple to try and change my mind about him, but my hatred that has the heat of a thousand suns has never wavered. I would like to think of myself as someone with a good gut instinct and judge of character, and he has rubbed me the wrong way since Day 1.

Recently, I found out that Zul has been messaging his partner’s friends rather unsavory texts. He’s been treating Iman’s friends as his own personal buffet to cheat with. I’ve heard from no less than three people about Zul’s attempted extra-curricular activities… and I suspect there may be more. And this hasn’t been the first time it’s happened either. I don’t want to break Iman’s heart, but I cannot abide by this horrible behaviour. Should I be the one to tell my best friend, or should I convince the friends that were texted to tell her themselves?

Yours,

Sleepless in Salambigar

Winnie: Yikes! Wading into friends’ romantic relationships is treacherous territory. However much we loathe our friend’s significant other, our friend is obviously not going to see what we see. The fact is, they can’t!

Loving someone makes one a lot more willing to accommodate their flaws. What looks to you as a glaringly negative personality trait in Zul, is to Iman, a minor imperfection. You must understand this to understand why rooting against the partner can be a no-win situation.

If Iman knows you feel strongly against someone she loves, it will ultimately drive a wedge between the two of you. And when it comes to choosing between a best friend or a romantic love, we all know who will win. And it’s not because you’re not valued as a friend, it’s just that romantic love brings with it the fairy tale we’ve all been conditioned to value the most: the happily ever after with the knight in shining armour.

You never explained what it was exactly that you did not like about him, other than a gut feeling that he was no good. Feeling is not fact. Did you ever tell Iman how you felt about him? If so, then you may already be perceived as being unfairly judgmental of him. However, I suspect – even if you were never candid to Iman about your thoughts on Zul – after two years, it’s likely that Iman was able to suss out how you feel.

Because of this, it’s unfortunate that, now that you have actual proof Zul is up to no good, you are not in a good position to break the news to Iman. You might as well be wearing a t-shirt with flashing lights that spell out “TOLD YOU SO”.

Even without any perceived bias, it’s already a difficult position to be in to find out your friend is getting cheated on. There are so many ways it could go wrong. They might “shoot the messenger” and resent you for telling them. They might choose to stay with the partner, and then avoid you because they feel embarrassed or judged. They might not even believe you and accuse you of wanting to break them up. Or, they might already know about their partner’s philandering and will get annoyed at you for getting involved in something that’s none of your business. Or, you can choose to not tell and they’ll get mad at you for not telling!

Now, there are loopholes and ways to mitigate the risk that comes with telling. Look into Iman’s stance on cheating. Has Iman previously been vocal about cheating being an unforgivable and heinous relationship crime? A strong position may make it more likely that Iman will react in the way that you hope and cut Zul out. No excuses, no second chances.

Another way is if you have a previous arrangement in place with Iman, where you agree to tell each other if a mate is cheating. I’ve had these discussions with friends, where I ask them what they would want me to do if I ever caught their partner cheating, and all have said that they would like to be told.

However, it’s easy to answer a question like that, theoretically. It’s a lot messier when it actually happens. Love forgives. And there’s no way to know for sure which way Iman will swing.

What’s your priority here? Is it to break up Iman and Zul (at the risk of hurting your friendship), or to preserve your friendship?

If it is to preserve your friendship, the safest option is to leave it to the friends that Zul hit on to tell Iman. If Iman finds out that you knew and gets upset you didn’t say anything, you are perfectly justifiable to say that it was not your place or your story to tell. It didn’t happen to you. It’s up to the people who got hit on to decide if they should tell.

If it’s more important to you to break them up and save Iman from Zul, then go ahead and tell. But do check yourself first and evaluate if you’re a bit too involved and invested in your friend’s love life. I understand that it’s painful to see your best friend be mistreated. But sometimes you’ve got to let things take their natural course, which means, no meddling.

You also need to prepare yourself on how to act if, or when, Iman does find out. It’s humiliating to be cheated on. As a best friend, you must be there without judgment. Iman can trash-talk Zul, but you will only listen – do not join in. This is in case they get back together.

You should also consider what you will do if Iman chooses to still stay with Zul. Can you accept it and continue to be civil to Zul? Or would it be a deal-breaker and a “Bye, Felicia!” situation?

Gosh, there’s so much to consider! I’m sorry if I’ve ended up making you less sure of what to do. But ultimately, you know your best friend better than I do. Feel out the situation and tread very carefully. Good luck!

Tiwin Aji is a Brunei-based comedienne known for her popular web series, #WinnieonWednesday. Equipped with empathy and a preternatural knack for doling out advice, she discovered at a young age that she loved telling people what to do.

If you’d like to get her take on your dilemma, fill out the contact form below or email your questions to hello@thescoop.co. Answers to reader-submitted questions will be published fortnightly in the ‘Winnie Wisdom’ column. All submissions will remain anonymous.