Dear Athena and Ares,
I like this guy a lot and we're always talking and laughing, and sometimes our eyes will lock for about five seconds. Does he like me? The problem is, his ex-girlfriend is one of my best friends. Should I ask him out or will my friend be mad?
First of all, everyone can be mature in this situation. If you're already hanging out with your friend's ex, then their break-up probably wasn't that bad. Everyone has to move on sometime; it is only healthy to learn from your past relationships, take that knowledge, and move on with your life.
That being said, people sometimes act irrationally in situations like this, so the most important thing is open communication. You won't ever know if the situation will upset your friend if you don't talk to her. And you might never know whether this guy likes you if you don't talk to him. If he does like you, trying a relationship could very well be worth it, although you should definitely move slowly.
You have to weigh the pros and cons: are you willing to risk your friendship for a guy? If you decide you are willing to take that risk, be very open with your friend. Explain why you like this guy, and tell her that her friendship means a lot to you. Friends are meant to support you and usually just want you to be happy, so give her some time.
In the end, she'll probably come to terms with her past and learn to be supportive of your romantic relationship. If you're smart about handling the situation, you might not have to choose between this guy and your friend.
You know the guy wants you, and if you go for him you know your friend will be mad. That is not the issue here. The issue is the age-old doctrine of "chicks before dicks" (known as "bros before hoes" for males) that stipulates you hold your friends over your romantic interests. Breaking this rule outright will bring you much agony, so you need to develop enough plausible deniability to protect you from any accusations. Luckily you can use the idea of male primo acio (Latin for first action). While some may think the idea of the boy making the first move is outdated and sexist, let's not forget that women can't pee standing up. Isn't it time gender differences worked in your favor?
Therefore, place hints to the guy that you are interested in him. Since he is a Rice guy, be extremely simple and direct like ‘I am hungry, ask me to dinner.' When you go on your date, you can tell your friend you just said yes to be polite. Next comes the most beautiful part of the plan. On the second date, your friend might accuse you again of taking her man. Now simply refer to precedent, and say that she was fine with the first date and that she is being a bad friend by not communicating her wants and being passive-aggressive. Accept her apology with the knowledge you have won.