I’ve dated my best friend’s younger sister for three years, and he doesn’t know about it. We happened to be in the same town, we got connected, and since then it’s been the two of us. His sister, at one point, came to live with me for over seven months before she finally got accommodation elsewhere.

My friend knows I’m cool with his sister but doesn’t know we’ve gone that far. The reason I’m sharing this story is that currently his sister is pregnant. That’s not a problem because we have plans to do something small and get married after the child is born. How to tell my friend about it is the problem. “Your sister is pregnant and I’m responsible” sounds like my death warrant.

“Don’t worry, I’m going to marry her as soon as possible” also sounds like I had no respect for our friendship. Due to how close we’ve been over the years, I want him to hear it from me. My girlfriend is already talking to her parents, but they don’t know I’m the man she’s talking about. The parents know me very well. Her mom treats me like a son anytime I’m around. Maybe she’ll be shocked too, but that is manageable as long as we are ready to get married.

How do I tell my friend in a way that also reduces the shock? I know there’ll be problems, but how do I manage it in such a way that it doesn’t affect our friendship?

—Pappy

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