When Your Best Friend Is Considering Cheating on Her Husband

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We all have that one friend—the one who knows all our secrets and has been by our side through thick and thin. For me, that’s my bestie, Lisa. We’ve been inseparable for over 30 years, ever since second grade. Back in the day, we would belt out Janet Jackson and Madonna songs using our curling irons as microphones, gossip about crushes, and plan our dream weddings. In our younger years, we partied hard, hitting clubs and living our best lives.

Now, our friendship feels more like sisterhood; we love each other fiercely and bicker like siblings do. We’ve supported one another through everything, and I think we both understand that with all the dirt we know about each other, it’s best to stay friends.

Recently, I returned to my hometown for a summer visit, and within days, Lisa and I were out for drinks, catching up on life. Most of our convo revolved around family trips and the usual updates. Then she dropped a bombshell: “I really need a girls’ trip! Let’s go somewhere warm and just forget everything, like we did in Vegas. You know, what happens in Vegas, stays in Vegas!”

This isn’t the first time Lisa has thought about straying. A few years back, she had a fling with an old coworker. One night of anger led her to dinner and then back to his place. She told me about it, and I didn’t hold back—after all, she had a devoted husband. But Lisa argued that the passion she felt with him was something she hadn’t experienced in her marriage for a while. I tried to hold her accountable, but I also understood her struggle.

That incident really put our friendship to the test. I had been through my own heartache when my daughter’s father cheated on me multiple times. Lisa stood by me as I navigated that pain, so I couldn’t help but feel confused about how she could even think about cheating. It took me a while, but I realized her choices were hers to make, not mine to judge. I thought guilt would consume her, but I can’t say for sure if it did.

Watching a close friend make questionable choices is really tough, though. I’m single now, so the idea of a tropical getaway sounds amazing—lying on a beach, sipping margaritas, and maybe flirting with a couple of cute guys. But the thought of going on a trip with Lisa, knowing her intentions, makes me feel anxious and even a little sick. I don’t want to be in a position where I either judge her or enable her bad decisions. A part of me wonders if we should just go and relive the good old days.

While I grapple with Lisa’s choices, the feminist side of me reminds me that both men and women can separate love from sex. We did it all the time in our 20s! Maybe a little adventure would empower her to deal with her marriage better. She mentioned that after her fling, it became easier to let go of her husband’s shortcomings. But I worry that one misstep could lead to more. Instead of working on her marriage with her husband and their therapist, she might just be looking for a one-night stand. If Oprah wouldn’t be cool with that, I’m sure Dr. Phil wouldn’t be either.

Maybe if Lisa has a weekend of wild fun, it would help her cope with her husband’s flaws. While I can’t condone her actions, knowing the full story of her marriage makes it easier for me to understand her. I’m not sure if we’ll end up booking that girls’ trip, but I do long for simpler times when decisions felt less complicated.

In summary, it’s challenging when a close friend is contemplating actions that could harm their relationships. The dilemma of wanting to support them while also feeling uneasy about their choices can be tough to navigate. Whether or not we take a trip together, I know I’ll always care for Lisa and hope she finds clarity.