>>1730796This is a very good question. One that I would have to put quite a bit of thought into.
Assuming these are prostitutes, personally, I would go for the "Thai milf" as you called the lovely woman in the example. You see, I chose the older women because she most likely would have had less "clients" than the younger female. So that would eliminate much of the nasty psychological baggage that would come with partaking in lovemaking. Speaking of nasty, an older woman would more likely be willing to get down and dirty than the younger girl, who could leave you and find another client. So you can be as intimate as you want and she would probably enjoy the intimacy more than the younger girl too.
Assuming that the women your friend offers you are not prostitutes, I would still choose the same. This is because I am not looking for a clingy girl that wants a long term relationship to rob me of my riches and then leave me. Going ahead and advancing on a Thai milf, she would already have the idea that I most likely would not want to have a long term commitment, and would be much more acceptable of saying our goodbyes. Now a big plus is that the milf would more than likely also NOT know how to use facebook to get in contact with me to reconnect, hell, she probably doesn't even have an account, so she couldn't contact my family members to ask about me (I don't use facebook personally).
tl;dr
You go young Thai--you gonna wanna die.