answer:If this were a friend of mine, and he wanted to keep the friendship with the other guy (let’s call him Joe), I would suggest talking to him: “Say, Joe, I know you and Shelley have split up. I’ve kept my distance from her all this time out of respect for our friendship. But if you two have moved on now, I want to let you know that I’m going to ask her out. I hope that won’t cause any problem between us.” However, the last time I did give this advice, it backfired, because Joe suddenly got all possessive (even though he’d been the one to do the breaking up) and did everything possible to put a wedge between the friend and Shelley. And it worked, too, because Shelley wasn’t really over him. The result was a lot of grief and hassle. In the end she walked away from both of them, and their friendship was never the same either. Love is a damned chancy business. All your friend can do is give it his best shot.