I've done these types of dates many times, and the success of the evening is always in the details.
A couple things that worked for me are to make sure that he knows my real first name, in a social situation you don't introduce by last names anyway - people won't expect it but using her real first name is important. If you do run into someone she knows you both can be very clear about the fact that you met in a social situation. If one of your colleagues has met her before, seen the pictures, etc. and decides to out her to you or your coworkers/friends you can simply say "wow, I had no idea. Thanks for the heads up." If on the other hand you run into someone she knows you already know her name and can simply say hello and nice to meet you before politely moving on.
I've also found that not only does age matter (you want to be within 'acceptable' age range) but experience does as well. If this is a work function select a lady that either has 'regular' work experience or is capable of mirroring the female colleagues. If you are 50, working in
Asset Management and recently divorced you don't want to become the gossip by taking a 20 year old student who believes that Asset Management is something to do with home building. Even a business student would seem inappropriate to your peers, however a 35 year old 'consultant' would be normal. On the flipside if you are 25 and recently graduated you don't want to take a 40 year old woman that works part time as an escort and has a marketing business on the side; as cool as the Ashton/Demi thing is it doesn't look professional to colleagues.
Finally meet the lady about an hour in advance, talk to her and get to know her a bit. The first time you hear the story about how you met, what she does, etc. shouldn't be in front of your friends and coworkers. Rather ask her the questions over a water/wine etc. alone and then if you would like any changes to the story to fit the social situation/status etc. you can suggest them in advance.
Unlike many on here I have found these to be some of the best dates, but it's very important to ensure you've done some advance planning.
) our son came down with a bad ear infection that day so my wife decided to stay home and I went with our friends.
