If you ask your friend: "Could you imagine me wearing glasses?" you would be giving them a cue to tell you if they had ever, in fact, seen you with glasses before. So they may reply either:
"Yes, in fact I have already seen you wearing glasses a few time." Or,
"Yes, I think I could imagine you wearing glasses." Or,
"No, I can't imagine what you would look like." So any response similar to one of these example replies would inform you whether you have been previously seen wearing glasses!
もし友達に、"Could you imagine me wearing glasses?"「私のメガネ姿を想像できる？」と聞くと、今まで自分のメガネ姿を見たことがあるかどうか、それとなく確認することができます。なので、友達は、
"Yes, in fact I have already seen you wearing glasses a few time."
「うん、実は何回かメガネかけているのみたことがあるよ。」
"Yes, I think I could imagine you wearing glasses."
「うん、メガネ姿が想像できる。」
"No, I can't imagine what you would look like."
「どんな風に見えるのか想像できない。」
などと答えてくれるでしょう。
*Have you ever seen me wearing glasses?
You can ask them using this sentence.
For example:
A:Have you ever seen me wearing glasses?
B:No never.
You can also this sentence to express yourself :"Have you ever seen me with glasses?"
Have you ever seem me wearing glasses?
以下のような会話で尋ねることができます。
例文：
A: Have you ever seem me wearing glasses?
私がメガネをかけているのを見たことがある？
B: No never.
一回もないよ。
または、"Have you ever seen me with glasses?"と聞くこともできます。
I don't think you have ever seen me wearing glasses.
▪ Did you ever see me wearing glasses?
This is asking the person in a direct way if he/she has ever see you wearing glasses.
▪ Have you ever seen me wearing my glasses?
This is asking the person in a direct way if he/she ever seen you wearing your glasses.
▪ I don't think you have ever seen me wearing glasses.
This is telling the person that they have not seen you wearing glasses and it is also asking him/her in an indirect way if they have or not.
Did you ever see me wearing glasses?
私がメガネをかけているところを見たことがある？
誰かに、自分がメガネをかけているのを見たことがあるか尋ねる直接的な言い方です。
▪ Have you ever seen me wearing my glasses?
私がメガネをかけているところを見たことがある？
上記同様、直接的な聞き方です。
▪ I don't think you have ever seen me wearing glasses.
私がメガネをかけているの見たことがないと思う。
相手に、自分のメガネ姿を見たことがないと言っている一方で、見たことがあるかないか間接的に尋ねる表現です。
I look like an idiot when I wear spectacles...Have you ever seen me in glasses?
Some people may feel awkward when they wear glasses...and so they only wear them when no one else is around. (in secret):-D
"I look like an idiot when I wear spectacles...Have you ever seen me in glasses?"
人が眼鏡をかけていると不思議な気分になる人もいますよね。
ですので、誰もいない時にしか眼鏡をかけない人もいます (内緒で):-D
【例】
"I look like an idiot when I wear spectacles...Have you ever seen me in glasses?"
（眼鏡をかけると私間抜けに見えます、私が眼鏡かけたとこ見た事ありますか？）
Two questions you can ask are: "Have you ever seen me when I'm wearing glasses?" or "Have you ever seen me with glasses on?" both carry/have the same meaning.
二通りの聞き方です：
"Have you ever seen me when I'm wearing glasses?"（私が眼鏡をかけているところ見たことある）
もしくは、
"Have you ever seen me with glasses on?"（私が眼鏡をかけているところ見たことある）
どちらも同じ意味です。
If you only wear glasses sometimes then your friend might not have seen you wear them so you might ask 'have you ever seen me wear glasses?
If you ask 'do you know i sometimes wear glasses?' this would tell you if they have seen you wear them
たまに眼鏡をかけるだけなら、友達でも眼鏡をかけたところを見たことがないかもしれませんね。
ですから、次のように聞けます。
'have you ever seen me wear glasses?'（私が眼鏡をかけているところ見たことある？）
また、
'do you know I sometimes wear glasses?'（私が時々眼鏡をかけるの知ってる？）
これでも、相手が「私」の眼鏡をかけたところを見たことがあるかどうかが分かります。
I don't think you've ever seen me wearing glasses, have you?
Have you seen me wearing glasses before?
Have you ever seen me with glasses on?
This sentence asks a question of whether or not someone has been seen wearing glasses.
The person doesn't seem to wear glasses often or not at all and so that is why the question is posed.
The following questions can also be asked:
How do you think I look with glasses on?
How do I look with these glasses on?
How would I look with glasses on?
Do you think I would look good with glasses on?
Would glasses fit my face?
ここでは、「私」が眼鏡をかけているところを見たことがあるかどうか尋ねています。これは、あまりあるいは全く眼鏡をかけない人がする質問だと思います。
次のような質問もあります。
How do you think I look with glasses on?（私に眼鏡は似合うと思う？）
How do I look with these glasses on?（私にこの眼鏡は似合うと思う？）
How would I look with glasses on?（私に眼鏡は似合うと思う？）
Do you think I would look good with glasses on?（私に眼鏡は似合うと思う？）
Would glasses fit my face?（私に眼鏡は似合うと思う？）
'Did you ever see me with glasses?''
This asks the other person if they have ever seen you wearing glasses, maybe you haven't known them a long time or you just haven't worn your glasses around them, but you need to make sure.
''Can you imagine me with glasses?''
This really prompts the other person to try to picture you in their mind wearing glasses. Maybe you have never worn glasses before, and you would like to ask them if it's something that they can imagine you wearing.
'Did you ever see me with glasses?''（私が眼鏡をかけているところ見たことある？）
これは、「私」が眼鏡をかけているところを見たことがあるかどうか尋ねています。まだ知り合って日が浅いとか、あるいは単にその人の前で眼鏡をかけたことがないというだけかれませんが、いずれにせよこれについて確認しています。
~~~~~~~~~
''Can you imagine me with glasses?''（私が眼鏡をかけているところイメージできる？）
これは相手に「私」が眼鏡をかけているところを想像してみるよう促します。あるいは一度も眼鏡をかけたことがなくて、想像できるかどうか聞いてみたいということかもしれません。
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