outsdr | Ahhh ... You're a wicked, naughty young man, aren't you, hmmm???

From a thread on Something Awful about embarrassing things that parents have done:

Captain Muffin

I once foolishly put my ex-girlfriends mothers mobile phone number in my phone as "<ex-girlfriends name> MOTHER". The reason for this was I often got the train to come see her at weekends and her mum worked next to the station so it was convenient for me to get a lift with her rather than wait for the bus.

So one day my ex is out in the stable and sends me a text along the lines of "I'm here in my riding gear and everyone has gone home, lets have fun in the hay". I was on the train on the way at the time. I send a nice and detailed reply, scroll to her name but go one too far and send it to her mother instead.

I got one back like five minutes later going "I'm glad to see you and my daughter are getting on so well!". Oh did that make for an awkward dinner time.

Chipyy

My flatmate did the same as above, but accidentally sent the message to his girlfriend's home phone number. In the UK if you do this, British Telecom will ring your landline and an automated service reads out the SMS. At the time the voice overs were recorded by Tom Baker, so his girlfriend's dad was essentially woken in the middle of the night by a dirty phone call from Doctor Who.

A midnight obscene phone call from Tom Baker would totally complete my life.

http://www.somethingawful.com/d/comedy-goldmine/embarrassing-situations-parents.php?page=1