(I have only recently acquired my first car. I know next to nothing about auto-maintenance, but I know I should check my oil. My parents are lesbians.)
Me: “Hey, mom? How do I check the oil in my jeep?”
Stepmom: “What?!”
Mom: “You mean you don’t know how?”
Me: “No…”
Stepmom: “Didn’t they cover that in your driver’s-ed class?”
Me: “Not really.”
Mom: “How could you have been raised by lesbians and not know how to check your oil?”
(I’m speechless for a second, but then I start laughing.)
Me: “Search me!”
(My mom starts speaking to my stepmom.)
Mom: “Honey, I’m going to go fulfill a stereotype, and show our daughter how to take proper care of a car!”

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514 Thumbs Up!)
(I accidentally answer a phone call from my brother instead of silencing it, while in the middle of making love to my girlfriend, who I haven’t told the family about. I brace myself for embarrassment when I talk to him next.)
Brother: “Did I really hear you—”
Me: “Yes.”
Brother: “With a girl?”
Me: *surprised* “Yes.”
Brother: “Sweet! [Mutual friend] owes me ten bucks.”
Me: “You bet I had a girlfriend?”
Brother: “No, he bet you were gay.”
(There is an awkward pause.)
Me: “Give him five back.”

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603 Thumbs Up!)
(My mom, stepdad, brother, close friend, and I are at a popular restaurant. I am a transgendered female to male, and my friend is also male. This makes my mom the only woman at the table. Mom is not 100% okay with my transition.)
Waitress: “Okay, so are we all ready?”
(We all nod.)
Waitress: “Sweet! Okay, so ladies first!”
(She turns to my mom. My mom looks at me.)
Me: “Well, mom, aren’t you ready to order yet?”
(My mom blushes.)
Mom: “Oh , I guess you meant me!”
(I think that was the first day mom really realized I am not a girl.)
Related:
Simple Genderalisation

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497 Thumbs Up!)
(My dad and I are eating dinner. The topic comes up of two incredibly homophobic people we know.)
Dad: “Yeah, I just feel sorry for their son when he comes out.”
Me: “Really? I don’t think that he’s gay. What made you think that?”
Dad: “Well, he’s in the drama club.”
Me: “Dad, I’m in drama club, and I’m not gay.”
Dad: “Are you sure?”
Me: “I have a girlfriend.”
Dad: “So did Elton John!”

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409 Thumbs Up!)
(My mom and I are visiting my grandmother for a few days. We help her make dinner, and sit down to eat. I can’t help noticing how she watches how I hold my fork.)
Grandmother: “I am so glad you don’t hold your fork like your brother!”
(My brother holds his fork with an outstretched pinky finger.)
Me: “What do you mean? Oh, the whole pinky thing? Yeah, I guess it’s a little weird.”
Grandmother: “Yes! I’m worried that when he does it, people will think he’s queer!”
(There is an awkward silence. I put down my fork.)
Me: “Um… what?”
Grandmother: “Queer! You know… gay!”
Mother: “We know what queer means, mother!”
(My mother and I were pretty weirded out by that statement. The kicker? I came out as a lesbian a couple of years after my grandmother’s passing, and I sure didn’t hold my fork the ‘queer’ way!)

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371 Thumbs Up!)