Q: I'm crazy for this girl. I've liked her for three years now, and we've been good friends for a while, but she's had a boyfriend that whole time -- and he's one of my good friends, too. In my fraternity, in fact. A few weeks ago, though, she and my friend finally broke up. She broke up with him and keeps telling me she's completely over it (she's hooked up with other people already), but he's incredibly upset about it. So upset that he hasn't come out for a fraternity event since the beginning of September. So, here's my dilemma: I'm dying to make a move on her, but I don't want my friend to kill me. I'm willing to wait until things have blown over a little bit, but it's our senior year, so it's not like I have all the time in the world. I want to let her know how I feel before we both move on to separate lives after college. What do you think I should do? How do I handle the situation?
A: Needless to say, this is a very sticky situation that requires delicate planning and execution. If executed the right way, though, she could become a fantastic new part of your life.
Let me first start by talking about you and your fraternity brother. I see only one way of dealing with the situation while upholding respect and dedication between brothers -- I am firm believer in the "bros before hoes" mantra, no matter the situation. With this in mind, you need to talk to your brother. Console him. Be empathetic.
Once you have made an honest attempt to be there for your brother, then you can delicately bring up your feelings for his ex. Make sure you at least make an attempt to get his permission to go ahead with this girl. The worst possible thing you can do is start hooking up or dating her without at least telling him and trying to figure out a way to solve both of your situations. It doesn't matter what this girl says about whether she is over it; if you are a real brother to this guy, you will talk to him before you move forward with this girl.
Now, about the girl situation. I do not believe for a second that she is "completely over it." If it has only been a couple weeks, then this girl could still be going through a post break-up coping period, where her coping method is hooking up with other guys. She probably still needs another week to settle in with her new single self before you should consider moving forward.
Assuming that your brother knows your plan and enough time has passed since the break-up, let's talk about the acquisition process. Your interactions with her over the next week and a half are crucial to the direction of your relationship with this girl. If she is invested in getting into a relationship with you, and you have sufficiently vetted her to make sure you are not just a rebound, then ask her out on a date.
If you don't know where to take her out on a date, see my first article for some great suggestions on campus. Off campus, I recommend Can Can or Ginger Thai in Carytown, and in downtown Richmond I recommend anywhere in Shockoe Bottom.
To make sure that everything I explained makes sense, here is a quick recap: approval and acceptance from brother plus the consideration of rebound with girl. If both of these are a non-issue, then you my friend are in the clear. Good luck, and I hope nothing but the best for you!