I once had to tell my parents that I was facing a felony charge for sex w/an underage girl. I was 18, she was 16. I don’t think that my relationship with my parents has been the same since. On the plus side, I do not have any criminal record.
When I was 16 I had to tell my parents I was dating a 21 year old. I was afraid that they wouldn’t let me see him if I told them and afraid that if I didn’t tell them they would find out and then use that as the excuse to not let me see him. I thought I was so in love that I would die if I didn’t get to date him. It turned out they were okay…but I wish they had not let me see him. 
I couldn’t call them since they’re deaf, so I once had to fax them the following note: “Mum, dad… try not to panic, but I got admitted to a mental hospital last night”. Heh.
Telling them I was quitting college, albeit temporarally.
- I was dropping out of college
followed a month later by - I’m preggers.
Yup. That was fun.
That my fiance was pregnant.
I didn’t have to tell them the time I was arrested because the cops called’em.
Me and you both MissTake, only mine was
- My husband’s been convicted of burglary and sentenced to a year in prison
followed a week later by - I’m preggers
- That I was in jail
- That I went to jail (again)
- I am an alcoholic
<Monty Python>
but… I got better
</Monty Python>
The hardest thing I ever told my parents was that my girlfriend, of 3 months, was moving in with me. Being from a very Catholic family (my father went to seminary but dropped out to marry my mother) this did not go over well. It resulted in several hours of lecturing and biblical quotes. Followed by several months of no contact.
I showed 'em though. The girlfriend became Mrs. Jim and just this month we celebrated 9 years of marriage.
That I crashed Mom’s car while they were off in the Caribbean on holiday… 
That my boyfriend was abusive.
I still haven’t told them that.
Of course, I did dump the abusive boyfriend and I’m now with my wonderful husband.
I think I was afraid to tell them because I didn’t want them to be right about him.
-
that I was pregnant ( at age 17, still in high school)
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that I was arrested and they had to come pick up my kids from the babysitters.
Both worked out well, I got married at age 17 and am still married. AND my dad offered to pay my fine-- he told me that its ok to stand up for what you believe in, even if it gets you into trouble.
That I was living with my boyfriend.
That I later was planning on marrying same.
Later, I was divorcing the same guy.
Still haven’t told them I met present hub on line.
I’m taking that to my GRAVE.
I struggled to tell my parents they were adopted.
OK, actually, telling them I was atheist wasn’t so easy, but only because I knew my mother (a do-as-I-say, not-as-I-do type of Christian) would flip. Ended up not talking to her for 3 weeks.
That I’m an athiest…
My mom, who has some faith that there exists a god but hasn’t gone to church in some 38 years, ever since I said 8 years ago that I didn’t want to go to a chruch service for christmas has been trying to get me into a chruch because she thinks I need to believe something.
Each time I mention that I’m not a follower of organized religion things get uncomfortable.
Hell, she was more understanding when she and my dad thought I was gay.
I just LOVE going home for the holidays.
On the plus side, their reaction is better than most of the people I know who I did NOT go to college with.
That I was gay.
Actually, I didn’t think it would be such a big deal. I had a brother who died in a mountain climbing accident, a brother with severe disabilities, TWO brothers that impregnated their respective girlfriends (one before he’d finished high school), a sister who’d been raped, a brother that got busted growing pot plants in the basement, not to mention several minor run-ins with the law involving drunken brawls and out-of-control parties amongst all of us, yet I never saw my mother get more upset than the night she found out about me. That’s a catholic mom for ya.
Me: Hi Mom.
Mom: Where’ve you been the last 3 days?
Me: Jail.
Mom: I thought so.
Me: What’s for dinner?
[sub]OK, so it wasn’t really that difficult. Now if I’d actually killed someone…[/sub]
I had to tell them that I missed a credit card payment once, and had a balance of $120.
Nothing interesting ever happens to me.
“What about James?”
(male friend I’ve known forever. Tall, broadshouldered, black hair, blue eyes. Yummy)
“Let’s not do this again.”
“Well, why not?”
“Okay, look. For the last time, no, I am not marrying James.”
“Why not? He obviously cares about and he’s such a sweet young man and certainly the most polite of the men you have brought home.”
“Mom…”
“What is it with you? You just have this thing for jerks? A nice guy would be too much? Your grandmother loves him, I like him, even your Dad likes him…”
“MOM! He’s gay!”
“…”
I told them that my (then) boyfriend was black. I grew up hearing that I would be disowned if I married a black man. So, it was really hard to tell them. But apparently, faced with the actual possibility that I might marry a black man, they backed down and were pretty cool about it. I didn’t marry him, though, as he turned out to be a jerk.