어려운 시기를 겪었잖아.

A: I feel bad for Bob. 어려운 시기를 겪었잖아.
B: I know. He just can’t seem to catch a break.
A: Things were looking up for a while, but all fell apart.
B: I’m sure he could use a good dose of moral support.

A: Bob이 불쌍해. He’s been through the wringer.
B: 그러게. 한시도 편할 날이 없네.
A: 일이 잘되는가 싶더니, 또다시 잘 안되고.
B: 정신적 지원이 많이 필요할 듯싶어.

[Additional expressions]
*I feel bad for Bob.
– I feel sorry about Bob’s situation. / I kind of pity Bob.
*He’s been through the wringer.
– He’s been going through a really hard time. / He’s had it rough.
*I know.
– I’m aware. / I hear what you’re saying. / I’m up to date on that.
*He just can’t seem to catch a break.
– Nothing seems to go right for him. / He’s got continuous bad luck.
*Things were looking up for a while
– He’s was doing OK for a bit / Things were all squared away for a time
*all fell apart
– everything went belly up / it all came crashing down / all went down the drain
*I’m sure he could use
– I’m certain it would be good for him to get / I know he’d benefit from
*a good dose of moral support
– a heaping amount of positive energy / some kind words from friends