A Chinese-language joke where near-identical sentences have different meanings: how do I translate this and find the humor? My friend sent me this on WeChat, and I'm told this is an amusing Chinese-language joke:

一、请写出下面两句话的区别在哪里？ 
1、冬天：能穿多少穿多少；夏天：能穿多少穿多少。  
2、剩女产生的原因有两个，一是谁都看不上，二是谁都看不上
3、女孩给男朋友打电话：如果你到了，我还没到，你就等着吧；如果我到了，你还没到，你就等着吧。
4、单身的原因：原来是喜欢一个人，现在是喜欢一个人。
二、附加题：
中国足球和中国乒乓球，一是谁都赢不了，二是谁都赢不了。

Question: How do I translate and find the humor in this?
This is my translation below (spoiler alert), but I don't understand much of the humor:

Winter: Can wear how much wear how much?  Summer: Can wear how much wear how much?  (穿多少穿多少)
No idea why this is funny, or how it's even grammatical.

&quot;Left over women&quot; arise in two ways: one is that nobody sees them (?), one is that everyone hates them (?).  (谁都看不上)
I probably didn't translate this well.

A girl gives her boyfriend a phone call: If you arrive, and I'm not there, you wait for me.  If I arrive, and you're not there, you wait for me.
I'm confident my translation is close to correct, but I don't see why this is funny (or even logical).

The reason for being a bachelor: at first, you like one person (一个人), but now you like being by yourself (一个人).
I think I've both translated this accurately, and understand the humor.

Additional question: Chinese football and Chinese table tennis: one nobody wins, the other nobody wins. (谁都赢不了)
I think the idea is that the Chinese football team always loses, so 谁都赢不了, but the Chinese ping pang team always wins, so for the other team 谁都赢不了.
I am a native Chinese speaker. Let me explain for you.

The humor: Every two sentences look the same but having totally different meanings.


  1、冬天：能穿多少穿多少；夏天：能穿多少穿多少。


Translate: Winter: Put on as much clothing as you can. Summer: Put on as fewer clothing as you can.

Explain: In the Winter sentence, 多少 is interpreted together, means "the quantity of the things that you have". In the sentence, it is exaggerated, and translate to "as much as you can". In the Summer sentence, 多少 should be interpreted separately as: 多 is an adjective "much", and 少 "a few", 多 is an adjective for 少, so 多少 means "very few".


  2、剩女产生的原因有两个，一是谁都看不上，二是谁都看不上


Background: 剩女 is a noun, means old girls (often older than 30) who are still single/unmarried. This is a slightly offensive word. 看上 means "falls in love with", 看不上 means "not falls in love with".

Translate: There are two reasons for being a 剩女: first, (she does) not fall for anybody; second, nobody falls for her.

Explain: The first sentence the "She" is an omission. For the second sentence, there is no omission, so 谁 is the body who is doing 看不上, and hence translates to "nobody falls for her".


  3、女孩给男朋友打电话：如果你到了，我还没到，你就等着吧；如果我到了，你还没到，你就等着吧。


Background: Most Chinese girlfriends are spoiled, and would demand much more from their boyfriends. And most Chinese take it for granted.

Translate: A girl gives her boyfriend a phone call: If you arrive, and I'm not there, you wait for me. If I arrive, and you're not there, you are going to wait for my punishment.

Explain: In Chinese, 等着 is a special word. In some occasions (depends on the context), 等着 translates to "give somebody a lesson". If someone is angry, he would say: 你给我等着. This means "I gonna get some helps and come back to punish you, you'd better stay here and do not go away." 


  4、单身的原因：原来是喜欢一个人，现在是喜欢一个人。


Yours is perfect.


  中国足球和中国乒乓球，一是谁都赢不了，二是谁都赢不了。


Your translation and understanding are both perfect.