Coworker's sister's dead baby. What should I say?

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One of my coworker's sister had to give birth to her baby which had died in the womb.

What should I say to him, I'm not sure what's appropriate: 'My condolences'? It doesn't seem right in this situation. 'I'm sorry'? It's not my fault. 'That's sad'? Surely he already knows that. 'I hope your sister is alright'? Of course she's not going to be alright right now.

Is this the time to offer a hug? A sad smile? A pat on the back? I didn't know what to do so when someone else told me I just avoided him so I didn't upset him further.

Also how upset should I expect him to be, I'd imagine that would be a really sad thing to happen, but I'm not thinking complete depression because it wasn't his baby and he never got a chance to know him/her. But saying that a girl I work with started crying when he said about it and she doesn't even know his sister, I mean yes it's sad but crying?

I need some help, I have no idea what to do in this situation. Can anyone give me some advice?

Er, don't make any dead baby jokes? For starters?

Well, depending on how close you and your coworker are you may not actually have to bring it up. I don't think you need to hug or touch him either. If he brings it up or you feel you have to say something, you could say "I'm sorry to hear about your loss. You must be worried about your sister." Just acknowledging his loss is probably enough (he did lose a family member and he's probably concerned for his sister). Since he's a coworker he's not likely to show too much emotion at work or even want to share an excessive amount of personal details about the event.

"Sorry about your loss" is a good place to start.

Anytime someone has experienced a death it is awkward to offer condolences. When we say I'm sorry for your loss, that does not mean that we would be responsible. We can say, I am sorry for your loss. Which really means I am sad that you are sad. Your presence and acknowledgement makes them feel better. When people avoid the person, it makes it more difficult. Hope this helps!

This is always tough for me, but my mom is really good at handing these situations like a charm.
First she will acknowlege their suffering by saying. OHHH how awful! Then she would ask if his sister was okay. and how was he handling the situation? Then she would listen to him. And then she would offer a token of help like Is there anything I can do to make things easier for her?? Does she need anything so she can rest?
Then she will finish with something like be strong and send your sister my love.

She should have been a grief councilor...she is really good at it. I try to immitate her, but easier said than done.

I would say the best thing to do is just be as simple as possible. A lot of people who don't even have Asperger's syndrome struggle with this type of thing. I would say say something along the lines "I am very sorry to hear about your loss. If you ever need someone to talk to about it, I am here for you."

Sometimes a handwritten card is the best thing as that shows you really care.

I recommend NOT bringing yourself into such as saying "I remember how such and such happened to me" but instead be 100% focused on them. A lot of non-Asperger's people make this mistake all the time: so often it's just two people have monologues instead of a dialogue.

I saw him at work today before I read all your very helpful comments so i couldn't put your advice into action but thank you very much.
I just didn't say anything about what happened but tried to be supportive. We work in a fast food retailer and it was really busy today so we didn't have much time not serving customers and I went on the till while he did the food prep so we weren't in the same place. We mainly talked about stuff that had to do with work anyway, there's been a lot of drama going on at the moment between other colleagues so we discussed that mainly. I don't think he really wants to talk about it or maybe he realises I'm not the right person to talk about it with.

He's done said things today that have confused me though, he was teasing and he said that it was because he was flirting. I don't know if this was just a joke or not but he has a wife and two children so I wouldn't have an affair/relationship with him anyway. I just didn't understand what he meant. Was that just a joke?