This is going to be a rather long post so I'm going to make up names to make this seem easier for you to read:

John - My friend
Ann - My friend's girlfriend
Kayla - HB

My friends John and Ann have been trying to hook me up with some girls lately because I'm single and they want to go on a double date with me and a girl. Ann has this friend, Kayla, that just got out of a long relationship and wants to hook me up with her that way it could be the four of us and we could go out and do things together since we all get along well. Ann is trying to get Kayla to come with the three of us this weekend to go and hang out.

I'm aware that I should be careful around a girl that just got dumped so that's why I'm coming here. I know what to use as openers and I know how to keep a conversation going, but I don't know what to talk about since she just got dumped. I also wouldn't want to mess anything up with her if I said the wrong thing at the wrong time.

Does anyone have any advice on what I can talk about and what I can do with a girl that's in that position? Should I just have friendly conversation with her until she feels better about being dumped? Should I try and flirt with her a little here and there to get her mind off him and more on me? I just need some ideas here.

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Hey man, here's a few tips from my side... Try to be the opposite of every dude that has been in a relationship for a long time... this is what girls on the rebound are looking for... Be "the cool, interesting guy" and talk about everything else but her recent relationship... if she wants to discuss the topic, let her know that you are not interested in such conversations (that ultimately lead to LJBF) by saying something along the lines of "If you go on I will have to charge you by the hour"... come up with interesting plans (parties, extreme sports, cool events, etc) and gauge her interest... do not openly invite her or show too much interest during this first encounter...

By the tone of your post I get that you value her a lot... this can only mess up your game, so become indifferent about the outcome... one more thing... flirting should come naturally and be part of who you are, watch some James Bond movies and you'll understand what I'm talking about... Good luck and keep us posted!

I get what you're saying. If she comes along this weekend I will definitely try what you suggested.

I like the whole, " If you go on I will have to charge you by the hour" plan, I will use that on her (if she talks about him of course)

I will keep you up-to-date as the weekend comes.

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Okay so here's a little post on what happened last night.

We all planned on going to see a movie last night and by the time we got there we realized the movie wasn't until 9:40P (it was around 8:00P when we found out) so we went back to Ann's house to pass the time.

We hung out in Ann's room for the most part so John and Ann did their own "thing" on the floor and Kayla and I just talked/flirted with each other on Ann's bed. I made her laugh A LOT, but we didn't touch or anything. I was getting some IOI's such as playing with her hair, and getting red in the face when we looked at each other.

Then came the movie. It wasn't what I expected at all really. She actually wanted to see the movie so when we got there she got all comfortable in her seat, put her legs up on the chair in front of her, and slid her hands - which were inside her sleeves - in between her legs. I didn't know what she wanted to I just kept my arm on the arm rest next to her so if she wanted to hold hands she could. Other than that she was just memorized by the movie the whole time.

I did notice her play with her hair a few times during the movie, I'm not sure if that meant anything though.

So that was the first date I guess you can say. I'm sure there will be some more in the future I will keep you updated with.

Please feel free to talk about what I can do or improve for next time.

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Here's one thing... movies make lousy dates, you cannot speak without getting the annoyed "shhh" from the other moviegoers, there's little kino escalation when, as you described, the target is caught in the movie... you should follow the movie at least with a drink or some clubbing later in the evening... otherwise it's kinda awkward to ask the target after sitting for two hours watching the movie to go to your place... you have to build momentum for that...