Can you undergo twice breaks with someone?

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I'm missing the boy who I said goodbye to last week.Should I call him? I keep distant with him because he does not have a stable job.Sounds ridiculous? But I did get much prssure from my family for that reason. I hope to be someone close with him,and he once told me"just let it be",but I'm afraid that if someday we break up again,both of us will be hurt painfully.Do I think too much?