AITA for not telling my boyfriend the truth when he asked how he “measures up”?

My boyfriend asked me to compare him to my past partners, insisting on full honesty. I gave him a kinder answer than the truth—and now I'm torn about whether to come clean or leave it alone.

I’ve only been with my boyfriend for a couple of months, but he’s genuinely one of the sweetest men I’ve dated. He plans surprises, cooks for me, rubs my feet after my runs, and just treats me with care in ways I wasn’t used to. I’ve had my fair share of experience—well into double digits—which he knows, and it’s never been a problem. He seemed a little curious and maybe intimidated, but it never affected us. Until recently, during pillow talk after s*x, when he insisted on knowing how he “compares” to the guys I’ve been with. I tried to dodge the question, but he pushed for full honesty, so I told him he was “a bit above average.”

I’m the girlfriend whose sweet, caring boyfriend wanted brutal honesty about how he measures up—so I gave him a gentler lie, and now I’m stuck wondering if keeping the peace makes me the villain.

The truth is, I didn’t answer honestly. He’s actually the smallest partner I’ve ever been with—noticeably so. I don’t remember every hookup in perfect detail, but I’m almost certain. Still, I genuinely don’t care; he treats me well, makes me feel safe, and is attentive in every way that matters. I just couldn’t bring myself to say something that would hurt him after he opened up like that.

"He wanted full honesty and kept pushing until I promised him the truth."

After I told him he was above average, he seemed grateful and relieved. But ever since, I’ve been stuck with this guilt. I know he trusted me to be transparent, yet I felt like honesty in that moment would’ve been cruel. Now I'm second-guessing whether protecting his feelings was the right call—or if lying, even for kindness, could backfire later.

"I didn’t want to humiliate him. But the guilt has been eating at me."

He trusts me, and that trust is what’s making this so messy. I don’t want to break his confidence, but I also don’t know whether bringing it up now would help anything—or just hurt him for no reason. I’m struggling to decide if honesty is still owed, or if the moment has passed and telling him would cause more harm than good.

🏠 The Aftermath

Nothing dramatic happened after the conversation—he accepted the compliment and seemed genuinely reassured. But internally, I’ve been spiraling over the lie.

He feels more confident, while I’m carrying this knot of guilt because I know what I said wasn’t accurate. There’s no fight, no conflict—just this quiet worry that someday the topic will resurface.

The real consequence is the tension between honesty and kindness, and the uncertainty about whether correcting a lie that made him feel good would only break his confidence unnecessarily.

"Sometimes the truth fixes nothing and only deepens insecurities."

I love how he treats me, and I value his vulnerability. That’s what makes this so heavy—hurting him feels unthinkable, but so does carrying a lie he specifically asked me not to tell.

💭 Emotional Reflection

This isn’t a story about anatomy—it’s a story about insecurity, vulnerability, and the delicate balance between truth and compassion in relationships. He asked a question that most people shouldn’t ask, and I tried to protect him from an answer that could shake his confidence.

Could I have told the truth? Yes. But honesty in that moment would’ve been more hurtful than helpful, especially since I’m genuinely satisfied with him and happy in the relationship.

People can debate whether transparency matters more than preserving feelings, but relationships often live in the gray space between blunt honesty and gentle reassurance.

Here’s how the community might see it:

“He never should’ve pushed that hard for a comparison. Some questions don’t need answers.”

“You protected his feelings. Telling the harsh truth now wouldn’t help anyone.”

“If he asks again, set boundaries. But digging up the truth after the fact might just damage his confidence for no reason.”

Reactions vary between defending his vulnerability, criticizing the question, and acknowledging the complicated nature of honesty in intimate relationships.

🌱 Final Thoughts

Sometimes kindness wins over brutal honesty, especially when the truth changes nothing about the relationship. Not every answer improves trust—some only inflame insecurities.

Still, carrying a lie can feel heavy, even when it was meant to protect someone you care about. Navigating that weight is part of the emotional labor of intimacy.

What do you think?
Is protecting someone’s confidence worth bending the truth? Or does honesty matter no matter how much it might sting? Share your thoughts below 👇

1 Comments

CherieiNovember 18, 2025 at 6:42 PM
He might not be very experienced and sounds insecure..so you made the right choice saying that about his size..you boosted his ego which was fragile..
If you say he was really small you know in your heart he woukd always be asking if you are satisfied..ultimately destroying your relationship..
Just let it go and know you did the right thing in telling him a small white lie