Advice from your humble blogger
If said "dating" took place in high school or the first two years of college it doesn't count. I'm sorry, it just doesn't. You're kids then, she doesn't know anything about you. Like, how much money you have, what kind of 401k plan is set up, where you live, what kind of car you drive, and if you have class or not. Considering all these issues can be resolved in high school and college based on how fast you can bong a beer, no, these years are completely out of the scenario. So if you're interested in a girl your buddy was going out with when he was 16 (and you are at least 22) just go for it. No permission even needed.
Escalation is key. If your friend was hooking up with some girl and never took it too serious, but you want to actually date her, this is fine. If you are willing to go at least one step further then your buddy, it's fair game. So if he met the girl at a bar and made out with her, and you would like to hook up with her on a regular basis, that's totally fine. As long as you're willing to take it more seriously then your friend, you're money.
If he cheated. I've got no love for cheaters. If he cheated, she's fair game to anyone. Double edged sword though. You can't use the cheating as a way to get close to her. So if you dig this girl and you know your buddy is cheating on her, you can't tell her about it to get close. That is a major no no.
I was thinking if your friend was the one that ended it, it would be okay to go for her. Upon further review, I don't think that's a good idea. If that is the case, you need to ask permission from your friend. Another double edged sword. If he says no to you dating her, the next five times you guys are out together he must yield to you first if there is a group of girls you are hanging out with before he makes a move on any of them. 10 times if you have irrefutable evidence that she would be really into you. i.e. e-mail, text, or a SWAK.
The plot to Pearl Harbor? Totally fine. If your friend goes off to war and is presumed dead, you and the so called "widow" get together after the fact. Then he shows back up because he was just just missing in action and not dead. You haven't done anything wrong but not must accept whatever her decision is. If she can't make one, a series of tests will take place to win her heart. They may include but are not exclusive to, arm wrestling, beer pong, 1 on 1 game of hoops, quarters, heads up Texas Hold Em, betting on the most random sporting act around (great during winter olympics because of events like Curling and the Spider), and of course a foot race to the girl, whoever touches her first wins. Basically play ground rules. They worked when you were five, they can work again.
Now, any and all of these rules can be broken if you get married. The problem there is you don't know if it's acceptable until years later because let's get real here, nobody that's stable dates a girl once and thinks they're getting married. Key word is stable. The even trickier part is, if you do decide to get married, do you invite said "friend/ex-boyfriend" to the wedding? If he is involved with another girl yes. If not and he isn't in the bridal party, no invite should be extended. That's just rubbing it in. If he is in the bridal party, he gets first pick on what girl to escort during the ceremony.
None of these rules apply to women. On more then one occasion I have been cited for saying women are the master sex. I believe that. When it comes to this though, absolutely not. Women will yes you to death to your face, then bad mouth you all over town, and if we're being brutally honest here, they are probably right to do so.
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