Dating advice please (for dealing with an older woman)?

Tomorrow night I am heading out to be a wing man for my buddy who is interested in a woman (let's call her Sue) in her early 40's (we are both in our early 30's). She will be bringing a friend (let's call Mary) out whom I have met on one other occasion (in a group outing). Long story short, they are both very attractive for their age but Mary who I will be left to entertain while my buddy chats up Sue, is kind of a kill-joy. She seemed to have a bit of a chip on her shoulder even as I casually chatted with her (I made zero sexual efforts on her and truth be told I'm not really that interested, short of her jumping my bones with no effort on my part). There is even good reason to believe that Mary c0ckblocked my friend from getting with Sue the first night (she invited him back to her place, but after a ride home with Mary, she didn't answer the door after he showed up)





My questions:


1) How would you handle a person like this in my role?


2) Why would a miserable person like that want to even BE in that type of situation again?Dating advice please (for dealing with an older woman)?
Looks like you are going to have to take one for the team.Dating advice please (for dealing with an older woman)?
Do her a favor. Stay home.





Why would a sophisticated, urbane, intelligent, experienced woman want to spend any time with a supercilious snotnose?





ETA: I REST MY CASE!! Thanks for proving my point. You have no idea what you're talking about. Stay home.
Why would she want to be in that awkward position?





Why do you?





I would deal with Ms. Ice Panties by staying far away.





Unless you owe your buddy a HUUUUGE favor.





Then just grin and edure it.
Make up a bowl of grain punch. Get the only hoot-nanny rockin and bang the dust out of her draws. I say do it for humanity.
Hang on to something and pray until she's finished :P. Yeah baby ;) lol
If they like each other so much, why is there a need for a wingman? He can't get her out alone?





In any case, as a wingman, it's your primary duty to see that the girl you're running interference on has a good time. This is easier said than done as some women go out with the mindset that they're not going to have a good time no matter what. My girlfriend has a friend like that - not only can she not have a good time, but if we're having a good time prior to her being there, she'll see to it that no one has fun after her arrival. We called her the funsucker.





My advice to you - Just let down any guard you have, have a few drinks, loosen up and keep your mind open. It's only for a night (although it certainly gets awkward if your friend hits it off with his date and expects you to hang out with the girls still). Smile, maintain eye contact, pretend you're interested, and be sure to keep her involved in the conversation - ask her questions (open ended ones).





If she's simply not into you or just cold as ice, there's really not much you can do other than be courteous and try to have fun regardless. From the sounds of it, your buddy owes you one.