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There was an article on AskMen.com about how to subtly date your ex's friend. Here was the main points of the article:
Don’t ask permission
Step one: Do not ask your ex for permission. She will almost always say “no,” even if the two of you are on good terms. Let’s be real. She doesn’t want you dating anyone, and she certainly doesn’t want you to date her friend. Moreover, as soon as you tell your ex that you’re interested in her friend, she’s going to start running interference. She’ll either directly tell her friend not to see you or she’ll start a subtle smear campaign behind your back.

Your best strategy is to build up attraction with her friend first. If your ex’s friend hasn’t been expressly told not to date you, she’ll be more receptive to your advances, and once a girl likes you, she’ll bend over backward to be with you. She’ll even jeopardize a friendship.
Flirt first
It’s possible that you’ve had an ongoing flirtation with your ex-girlfriend’s friend. Maybe you’ve shared a few lingering glances, some inside jokes, or even a little friendly physical contact. In this respect, picking up your ex’s friend might actually be easier than picking up a stranger. Think about it: You’ve already established a comfort level. Now that you’re single, all you have to do is ratchet up the flirtation a bit. Introduce some sexual innuendo into your standard teasing and gauge her response.
Exploit natural rivalries
It’s a fact of nature: Women are competitive. Even friends -- scratch that, especially friends -- can be jealous of one another. Women compete, particularly for men, and you can use this fact to your advantage when trying to date your ex’s friend. Dating a friend’s ex can be a real ego boost for a woman. You become a tangible sign of her greater desirability, intelligence and beauty.

You can exploit natural rivalries by using very specific types of compliments. Tell her things like “I’ve never met a girl like you before.” Even though you haven’t mentioned your ex by name, her friend’s mind will immediately go there. She’ll recognize that you’re making a comparison between her and your ex, and that she’s coming out on top. One word of caution about natural rivalries: For the same reason her friend will be attracted to you, your ex might start second-guessing the breakup. Be prepared for your ex to make a play for you if you start to date her friend. Do not give in; it’s not you she’s thinking about, it’s all about competing with her friend.
Prepare for the fallout
It’s only a matter of time before your ex finds out you’ve decided to date her friend. When she finds out, she’s probably going to flip out, especially since (if you’ve followed our advice) you’ve been dating her friend behind her back.

If possible, be the one to tell your ex the news (unless her friend volunteers). Don’t let your ex hear the news from someone else and try to avoid scenarios that will cause a scene. For example, don’t surprise your ex by showing up to a party with her friend on your arm. That kind of behavior will result in a three-way screaming match, or possibly even a full on hair-pulling, eye-scratching catfight. (We know it might sound cool, but it’s not.)

If you date her friend, there are going to be consequences. Your main objective is to keep those consequences from being so unpleasant that your ex’s friend will decide the relationship isn’t worth the stress. A little drama can bring you closer together. A lot of drama can kill any chance you have of dating her friend.
it might just be worth it
Date her friend and there will be trouble। It’s certainly not the easiest path to romantic fulfillment. However, if you follow these tips for dealing with your ex while seducing her friend, you’ll see that the task is far from impossible. Just remember, whatever you do, never suggest a threesome.


Ok first of all, this is hilarious. Do NOT ask men. Secondly, a real female, wouldn't compromise their friendship for a man-well it least I wouldn't. If you try and make me competitive sorry-I don't fight for dudes. And lastly, unless you wanna get slapped upside your head, don't ask me to have a threesome. LOL