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Etiquette and tips for setting up dates

post #1 of 11
Thread Starter 
My best friend is 31, single, and is doing well for himself. He is very smart and logical (engineer background), but with an attitude to match. Some would say he's socially somewhat awkward, or immature, or even borderline socially inadequate. That is to say, he says what's logical but not necessarily proper for the situation when he does speak, and the conversation stoppers can be somewhat hard to recover from. To give you a vivid example, think Jack Nicholson in As Good As It Gets. And I have taken it upon myself to find him a good woman. Today I managed to set up a dinner. The dinner party comprised of myself (married), a married couple (friends of mine who are friends with the woman), the woman, and my friend. We went to Dave & Busters to eat dinner and played the games afterwards. D&B turned out to be a poor choice because it was too loud. Not much real conversation. I'll also admit I did a poor job carrying the conversation. Fortunately my friend (wife of the married couple) helped a great deal. I think we can get better at this with practice. It looks like my friend MAY get another shot at her based on the ladies' room conversation and that she said she'll use the D&B (with some credits left) for "next time." Today I didn't get much good words in for my friend, and I plan to do it next time. Could you enlighten me with your experience on this topic? Some of the things I can think of now are 1. the proper etiquette, 2. picking the location and things to do 3. who pays the bill 4. things to lookout for/reminders for someone in my role Any thoughts/experiences on this matter is greatly appreciated. BTW, she's really cool and I like her.
post #2 of 11
Nice of you to help out a friend. Since you have already made the intro, I think it is now up to your friend and the single girl to see if they would like to have a date by themselves. If not, don't force the issue. I don't think you should arrange another group date. They are both adults and should be able to manage without you.

For what its worth, I think D&B was a good idea, as it created a good opportunity for distraction and an activity to focus on. It is also large enough to let people pair off separately for a while. Payment etiquette depends on what you had. If it was a few pitchers that were shared, one check is appropriate and you could offer to pay. If everyone had dinner, each couple should pay. If the singles had a great time, your friend could offer to pay for the girl in a non-awkward way.
post #3 of 11
Etiquette for setting up dates - DONT.

Let the women do this and cause frustration and take your friend out to the bar and be a good wing man. That's a hell of a lot better than setting up a random dinner. It can only end up to ways: They get married and live happily ever after ... or Bad. Most likely it'll end poorly.

Exception: If she is SUPER hot. Then it's acceptable to setup a friend. IF she says it's ok.
post #4 of 11
Well, to me honest, you can't trick a girl into liking a guy that is socially awkward. Either she knows or will find out eventually. A girl will have to like him for who he is. That or he has to do a little more research on this topic and decide for himself that he needs to improve his social skills. Practice is good though. It seems like the women in your group are having some fun with this situation, they love to play matchmaker, just let them handle his affairs.
post #5 of 11
Does your friend want to meet her? If yes, then he needs to call her himself and set up a date at a nice quiet restaurant.
post #6 of 11
find a way to get him moderately but not stumbling drunk to get the edge off his social awkwardness. a dinner will be pretty awkward in a group where everyone basically knows its a setup. maybe a shared birthday party or a "wine tasting" or something.

"real conversation" isn't a good way to start off. Just have fun first.
post #7 of 11
People are who they are and you shouldn't try to change that. Heck, I am sure some ladies would find that sort of guy charming in his own way.
post #8 of 11
I think all that needs to be done is get him out and about and to attend lots of social gatherings and make him meet lots of people.

That's all you should do and all you need to do. Once he meets someone right, things just happen and conversations flow freely, because he will be comfortable and so will she.
post #9 of 11
Every time someone has tried to set me up it has ended up a bigger dissapoint for the person who set me up than for me or the girl. I had found in my cases that the person doing the setting up had overly emotionally invested in the end result rather than thinking through whether I and the girl for that matter had anything in common. I do therefore not believe in setting people up.
post #10 of 11
^^ +1 I've always found disappointing and sabotaging dates -- set up by those friends who enjoy playing matchmake -- to be a source of great entertainment.
post #11 of 11
People who speak in metaphors should shampoo my crotch.
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