When 吧 (ba) is used twice in a sentence, it is used to list two options that the speaker is debating. It gives the sentence an indecisive feel, as though the speaker doesn't know which one to choose. This construction often has a negative connotation, since the options usually are not ideal.

冬天去吧，太冷；夏天去吧，太热。 Dōngtiān qù ba, tài lěng ; xiàtiān qù ba, tài rè.Going in the winter is too cold, going in the summer is too hot.
工作吧，太累；不工作吧，无聊。 Gōngzuò ba, tài lèi ; bù gōngzuò ba, wúliáo.Working is too tiring; I'll be bored if I don't.
买吧，不想花那么多钱；不买吧，又不开心。 Mǎi bā, bù xiǎng huā nàme duō qián ; bù mǎi bā, yòu bù kāixīn. If I buy it, too expensive, but if I don't buy them, I won't be unhappy.
早去吧，需要等；晚去吧，会堵车。 Zǎo qù bā, xūyào děng ; wǎn qù bā, huì dǔchē. If we go early we'll have to wait, but if we go later, there will be too much traffic.
不说吧，他还会做错；说吧，他肯定不高兴。 Bù shuō ba, tā hái huì zuò cuò ; shuō ba, tā kěndìng bù gāoxìng.Not telling him, he will still do it wrong next time; Telling him, he must be upset.
回去吧，机票太贵；不回去吧，家人肯定会想我。 Huíqù ba, jīpiào tài guì ; bù huíqù ba, jiārén kěndìng huì xiǎng wǒ.Going back, the air ticket is too expensive; Not going back, my family definitely miss me.

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Source and Further Reading