Oh well就是表示有点遗憾，或者是以玩笑的口吻假装不安的情绪。

例句：Did you hear, the football team won't make the playoffs this year. Oh well, that's too bad. （听说了吗，足球队今年不能参加决赛。唉，有点糟糕。）

例句：You're not going to give me any chips? (teasing) Oh well, I guess I won't be able to give you a ride home. （你不给我薯片？（开玩笑）唉，那我只好不让你坐我的车回家了。 ）