Background
My best girlfriend got divorced about a year ago. i won't go into all the reasons for that, but she was very justified in leaving the marriage. since she left her husband, she has had a string of about 4 guys, all of which have either not lasted or been total and complete psychotic fuckups. She is having some pretty shitty luck, so her m.o. now is to just let things go. She isn't planning on getting serious with anyone, she jsut wants to date, have a good time, make friends.

the dilemma. she has met this dude that she really wants to ask her out. he has said some things that make her think he is into her, but it's been awhile since she really had a "crush" on someone and is not sure how to proceed at this point. she came to me for advice, but I've not dated in almost ten years and have no idea to start.

here's where you come in. How does she proceed from there. she's interested in the dude, and she wants him to know it, but she also wants him to know she doesn't want to get serious. she's also too old fashioned to just ask him out, she wants him to do the asking.

Plus, there are some conflicts that she's dealing with - first and foremost, it's her mom's boss.

help a sister out!

I wouldn't even go there. It's not worth causing conflict between mother and daughter. What if it doesn't work out and he's a jerk. He could get really nasty towards the mom concerning her work. You never know.
Just my humble opinion.

__________________
I am here for only a short time on this earth. My goal is to make everyone I see smile if only for a moment.

Hmmm.....I wouldn't flirt with my mom's employees either. Of course, I think it depends how many options exist in town....if it's a small place, there might not be a choice.

I'd just be friendly and a bit flirtatious and see if I could "encourage" him a bit. Generally, the men that I have dated have wanted to preserve their self-confidence, and only asked me out when they were certain that I would say "yes."

__________________
Life is too short not to love and be loved....preferably multiple times in one night.

I think men talk to women so they can sleep with them and women sleep with men so they can talk to them. ~ Jay McInerney

osuche is correct most men will only ask if they know what the answer will be for sure, the best thig to do is just let him know that you are interrested in him and let it go from there. As for the moms boss thing i would not touch that. It can cause a bad reaction if it does not go well which would not be good for the mother. just my two cents and all

__________________
May you live as long as you want, and want as long as you live!!!!!!!!!!!!