1: Winter: wear as much as possible, summer: wear as little as possible.
多少 means "how much", but could be read as 多+x "how very x", with x here being 少 （little).
2: 看不上 is ambiguous. She won't give anybody a thought. or Nobody gives her a thought.
3: "... then you just keep waiting." vs. "... then you can wait for your punishment."
4: 喜欢一个人 can mean "to like a person", can also mean "to like to be alone" (a verb like 生活 is implied, 一个人 is an adverb here).
5: 喜欢上 can be read as "started to like" vs. "would like to fuck" with 上 being read differently.
6: 睡过了: "he overslept" vs. "has slept (with her) before".
In winter wear as much as you can; In summer wear as less as you can.
Two reasons: nobody likes her; she likes nobody.
She tells her BF: if you comes here early than me, just wait; if I come here early than you, watch yourself.
Reason of don't have BF/GF: ago I like single, now I like he/she.(don't like others)
Reason of a boy likes(or
is fond of) a girl: he likes her; he want to ML with her.
Reason of a boy was late for appointment: wake up late(oversleep); was slept with the girl.
P.S. 英语不好，希望能看懂 O(∩_∩)O~
P.S. My English is not very good, I hope you can understand. O(∩_∩)O~
These are some interesting Chinese wording and grammar patterns 冬天能穿多少穿多少：多少is one word as a whole. 夏天能穿多少穿多少：多is an adv. for 少
谁都看不上：谁in this sentence could be sub. or obj. In Chinese obj. may be not following verb, but at the beginning
一个人：may be someone (refer to other person), or being alone (refer to oneself)
喜欢上：上could be a 助词 (English has no such part of speech) for 喜欢, means "have fallen in love", or a verb (oral using only, means f**k)，喜欢is the predicate, means "love to f**k"
睡 could be sleep, also, only in oral using, could be f**k. 睡过means "slept for too long", or "f**ked"